MDMA - wikipedia MDMA Not to be confused with MDA, EDMA or 2, 3 - MDMA. MDMA INN : Midomafetamine Clinical data Pronunciation methylenedioxymethamphetamine : / ˈmɛ. θɪ. liːn. daɪ. ˈɒk. si. / / ˌmɛθæmˈfɛtəmiːn / Synonyms 3, 4 - MDMA ; Ecstasy ( E, X, XTC ) ; Molly ; Mandy ; AHFS / Drugs.com MDMA Dependence liability Physical : not typical Psychological : moderate Addiction liability Low -- moderate Routes of administration Common : by mouth Uncommon : snorting, inhalation ( vaporization ), injection, rectal Drug class empathogen -- entactogen stimulant ATC code none Legal status Legal status AU : S9 ( Prohibited ) BR : Class F ( Prohibited substances ) CA : Schedule I DE : Anlage I ( Authorized scientific use only ) NZ : Class B UK : Class A US : Schedule I UN : Psychotropic Schedule I Pharmacokinetic data Metabolism Liver, CYP450 extensively involved, including CYP2D6 Metabolites MDA, HMMA, HMA, DHA, MDP2P, MDOH Onset of action 30 -- 45 minutes ( by mouth ) Biological half - life ( R ) - MDMA : 5.8 ± 2.2 hours ( variable ) ( S ) - MDMA : 3.6 ± 0.9 hours ( variable ) Duration of action 4 -- 6 hours Excretion Kidney Identifiers IUPAC name ( RS ) - 1 - ( 1, 3 - benzodioxol - 5 - yl ) - N - methylpropan - 2 - amine CAS Number 42542 - 10 - 9 PubChem CID 1615 IUPHAR / BPS 4574 DrugBank DB01454 ChemSpider 1556 UNII KE1SEN21RM KEGG C07577 ChEBI CHEBI : 1391 ChEMBL CHEMBL43048 PDB ligand B41 ( PDBe, RCSB PDB ) Chemical and physical data Formula C H NO Molar mass 193.25 g mol 3D model ( JSmol ) Interactive image Chirality Racemic mixture Boiling point 105 ° C ( 221 ° F ) at 0.4 mmHg ( experimental ) SMILES CC ( NC ) CC1 = CC = C ( OCO2 ) C2 = C1 InChI InChI = 1S / C11H15NO2 / c1 - 8 ( 12 - 2 ) 5 - 9 - 3 - 4 - 10 - 11 ( 6 - 9 ) 14 - 7 - 13 - 10 / h3 - 4, 6, 8, 12H, 5, 7H2, 1 - 2H3 Key : SHXWCVYOXRDMCX - UHFFFAOYSA - N ( verify ) 3, 4 - Methylenedioxymethamphetamine ( MDMA ), commonly known as ecstasy ( E ), is a psychoactive drug used primarily as a recreational drug. The desired recreational effects include increased empathy, euphoria, and heightened sensations. When taken by mouth, effects begin after 30 -- 45 minutes and last 3 -- 6 hours. As of 2017, MDMA has no accepted medical uses. Adverse effects of MDMA use include addiction, memory problems, paranoia, difficulty sleeping, teeth grinding, blurred vision, sweating, and a rapid heartbeat. Use may also lead to depression and fatigue. Deaths have been reported due to increased body temperature and dehydration. MDMA increases the release and slows the reuptake of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain. It has stimulant and psychedelic effects. The initial increase is followed by a short - term decrease in the neurotransmitters. MDMA belongs to the substituted methylenedioxyphenethylamine and substituted amphetamine classes of drugs. MDMA was first made in 1912. It was used to improve psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s. MDMA is commonly associated with dance parties, raves, and electronic dance music. It is often sold mixed with other substances such as ephedrine, amphetamine, and methamphetamine. In 2014, between 9 and 29 million people between the ages of 15 and 64 used ecstasy ( 0.2 % to 0.6 % of the world population ). This was broadly similar to the percentage of people who use cocaine, amphetamines, and opioids, but fewer than for cannabis. In the United States, about 0.9 million people used ecstasy in 2010. MDMA is generally illegal in most countries. Limited exceptions are sometimes made for research. Researchers are investigating whether a few low doses of MDMA may assist in treating severe, treatment - resistant posttraumatic stress disorder ( PTSD ). In November 2016, phase 3 clinical trials for PTSD were approved by the United States Food and Drug Administration ( FDA ) to assess effectiveness and safety. The FDA granted MDMA a breakthrough therapy designation for the treatment of PTSD in August 2017. Contents 1 Effects 2 Use 2.1 Recreational 2.2 Medical 2.3 Other 2.4 Forms 3 Adverse effects 3.1 Short - term 3.2 Long - term 3.3 During pregnancy 3.4 Reinforcement disorders 3.5 Harm assessment 4 Overdose 5 Interactions 6 Pharmacology 6.1 Pharmacodynamics 6.2 Pharmacokinetics 7 Chemistry 7.1 Synthesis 7.2 Detection in body fluids 8 History 8.1 Early research and use 8.2 Shulgin 's research and early use in therapy 8.3 Rising recreational use 8.4 Media attention and scheduling 8.4. 1 United States 8.4. 2 United Nations 8.5 Post-scheduling 9 Society and culture 9.1 Legal status 9.1. 1 Australia 9.1. 2 United Kingdom 9.1. 3 United States 9.1. 4 Netherlands 9.1. 5 Canada 9.2 Demographics 9.3 Economics 9.3. 1 Europe 9.3. 2 North America 9.3. 3 Australia 9.3. 4 Corporate logos on pills 10 Research 11 Notes 12 References 13 External links Effects In general, MDMA users report feeling the onset of subjective effects within 30 -- 60 minutes of MDMA consumption and reaching the peak effect at 75 -- 120 minutes, which then plateaus for about 3.5 hours. The desired short - term psychoactive effects of MDMA have been reported to include : Euphoria -- a sense of general well - being and happiness Increased self - confidence, sociability and feelings of communication being easy or simple Entactogenic effects -- increased empathy or feelings of closeness with others and oneself Relaxation and reduced anxiety Increased emotionality A sense of inner peace Mild hallucination Enhanced sensation, perception, or sexuality Altered sense of time The experience elicited by MDMA depends on the dose, setting, and user. The variability of the induced altered state by MDMA is lower compared to other psychedelics. For example, MDMA used at parties is associated with high motor activity, reduced sense of self - identity as well as poor awareness of the background surroundings. Use of MDMA individually or in a small groups in a quiet environment and when concentrating, is associated with increased lucidity, capability of concentration, sensitivity of aesthetic aspects of the background and emotions, as well as greater capability of communication with others. In psychotherapeutic settings MDMA effects have been described by infantile ideas, alternating phases of mood, sometimes memories and moods connected with childhood experiences. Sometimes MDMA is labelled as an `` empathogenic '' drug, because of its empathy - producing effects. Results of different studies show its effects of powerful empathy with others. When testing the MDMA for medium and high dosage ranges it showed increase on hedonic as well as arousal continuum. The effect of MDMA increasing sociability is consistent, however effects on empathy have been more mixed. Use Recreational MDMA is often considered the drug of choice within the rave culture and is also used at clubs, festivals and house parties. In the rave environment, the sensory effects from the music and lighting are often highly synergistic with the drug. The psychedelic amphetamine quality of MDMA offers multiple reasons for its appeal to users in the rave setting. Some users enjoy the feeling of mass communion from the inhibition - reducing effects of the drug, while others use it as party fuel because of the drug 's stimulatory effects. MDMA is used less frequently than other stimulants, typically less than once per week. MDMA is sometimes taken in conjunction with other psychoactive drugs known as such as LSD, psilocybin mushrooms, and ketamine, an act called `` candy - flipping ''. Medical See also : MDMA § Research As of 2017, MDMA has no accepted medical indications. Before it was widely banned, it saw limited use in therapy. Other A small number of therapists continue to use MDMA in therapy despite its illegal status. Small doses of MDMA are used as an entheogen to enhance prayer or meditation by some religious practitioners. MDMA has been used as an adjunct to New Age spiritual practices. Forms MDMA has become widely known as ecstasy ( shortened `` E '', `` X '', or `` XTC '' ), usually referring to its tablet form, although this term may also include the presence of possible adulterants or dilutants. The UK term `` mandy '' and the US term `` molly '' colloquially refer to MDMA in a crystalline powder form that is thought to be free of adulterants. MDMA is also sold in the form of the hydrochloride salt, either as loose crystals or in gelcaps. In part due to the global supply shortage of sassafras oil, substances that are sold as molly frequently contain no MDMA and instead contain methylone, ethylone, MDPV, mephedrone, or any other of the group of compounds commonly known as bath salts. Powdered MDMA ranges from pure MDMA to crushed tablets with 30 -- 40 % purity. MDMA tablets typically have low purity due to bulking agents that are added to dilute the drug and increase profits ( e.g., lactose ) and binding agents. Tablets sold as ecstasy sometimes contain 3, 4 - methylenedioxyamphetamine ( MDA ), 3, 4 - methylenedioxyethylamphetamine ( MDEA ), other amphetamine derivatives, caffeine, opiates, or painkillers. Some tablets contain little or no MDMA. The proportion of seized ecstasy tablets with MDMA - like impurities has varied annually and by country. The average content of MDMA in a preparation is 70 to 120 mg with the purity having increased since the 1990s. MDMA is usually consumed by mouth. It is also sometimes snorted. Ecstasy tablets which may contain MDMA A salt of MDMA ( typically white ) with impurities, resulting in a tan discoloration Crushed MDMA ( 1 gram ) crystals High purity MDMA in capsules Adverse effects Short - term The most serious short - term physical health risks of MDMA are hyperthermia and dehydration. Cases of life - threatening or fatal hyponatremia ( excessively low sodium concentration in the blood ) have developed in MDMA users attempting to prevent dehydration by consuming excessive amounts of water without replenishing electrolytes. The immediate adverse effects of MDMA use can include : Dehydration Hyperthermia Bruxism ( grinding and clenching of the teeth ) Increased wakefulness or insomnia Increased perspiration and sweating Increased heart rate and blood pressure Increased psychomotor activity Loss of appetite Nausea and vomiting Diarrhea Erectile dysfunction Visual and auditory hallucinations ( rarely ) Mydriasis The adverse effects that last up to a week following cessation of moderate MDMA use include : Physiological Trismus Loss of appetite Insomnia Tiredness or lethargy Psychological Anxiety or paranoia Depression Irritability Impulsiveness Restlessness Memory impairment Anhedonia Long - term As of 2015, the long - term effects of MDMA on human brain structure and function have not been fully determined. However, there is consistent evidence of structural and functional deficits in MDMA users with a high lifetime exposure. In contrast, there is no evidence of structural or functional changes in MDMA users with only a moderate ( < 50 doses used and < 100 tablets consumed ) lifetime exposure. MDMA use at high doses has been shown to produce brain lesions, a form of brain damage, in the serotonergic neural pathways of humans and animals. It is unclear if typical MDMA users may develop neurotoxic brain lesions. Long - term exposure to MDMA in humans has been shown to produce marked neurodegeneration in striatal, hippocampal, prefrontal, and occipital serotonergic axon terminals. Neurotoxic damage to serotonergic axon terminals has been shown to persist for more than two years. Elevations in brain temperature from MDMA use are positively correlated with MDMA - induced neurotoxicity. Adverse neuroplastic changes to brain microvasculature and white matter also occur in humans using low doses of MDMA. Reduced gray matter density in certain brain structures has also been noted in human MDMA users. Global reductions in gray matter volume, thinning of the parietal and orbitofrontal cortices, and decreased hippocampal activity have been observed in long term users. The effects established so far for recreational use of ecstasy lie in the range of moderate to large effects for SERT reduction. Impairments in multiple aspects of cognition, including attention, learning, memory, visual processing, and sleep have been found in regular MDMA users. The magnitude of these impairments is correlated with lifetime MDMA usage and are partially reversible with abstinence. Several forms of memory are impaired by chronic ecstasy use ; however, the effect sizes for memory impairments in ecstasy users are generally small overall. MDMA use is also associated with increased impulsivity and depression. Serotonin depletion following MDMA use can cause depression in subsequent days. In some cases depressive symptoms persist for longer. Some studies indicate repeated recreational users of ecstasy have increased rates of depression and anxiety, even after quitting the drug. Depression is one of the main factors for cessation of use. At high doses, MDMA induces a neuroimmune response which, through several mechanisms, increases the permeability of the blood - brain barrier, thereby making the brain more susceptible to environmental toxins and pathogens. In addition, MDMA has immunosuppressive effects in the peripheral nervous system and pro-inflammatory effects in the central nervous system. During pregnancy Addiction experts in psychiatry, chemistry, pharmacology, forensic science, epidemiology, and the police and legal services engaged in delphic analysis regarding 20 popular recreational drugs. Ecstasy was ranked 16th in dependence, physical harm, and social harm. MDMA is a moderately teratogenic drug ( i.e., it is toxic to the fetus ). In utero exposure to MDMA is associated with a neuro - and cardiotoxicity and impaired motor functioning. Motor delays may be temporary during infancy or long - term. The severity of these developmental delays increases with heavier MDMA use. Reinforcement disorders Approximately 60 % of MDMA users experience withdrawal symptoms when they stop taking MDMA. Some of these symptoms include fatigue, loss of appetite, depression, and trouble concentrating. Tolerance to some of the desired and adverse effects of MDMA is expected to occur with consistent MDMA use. A 2007 analysis estimated MDMA to have a psychological dependence and physical dependence potential roughly three fourths and four fifths that of cannabis. MDMA has been shown to induce ΔFosB in the nucleus accumbens. Because MDMA releases dopamine in the striatum, the mechanisms by which it induces ΔFosB in the nucleus accumbens are analogous to other dopaminergic psychostimulants. Therefore, chronic use of MDMA at high doses can result in altered brain structure and drug addiction, which occur as a consequence of ΔFosB overexpression in the nucleus accumbens. MDMA is less addictive than other stimulants such as methamphetamine and cocaine. Compared with amphetamine, MDMA and its metabolite MDA are less reinforcing. One study found approximately 15 % of chronic MDMA users met the DSM - IV diagnostic criteria for substance dependence. However, there is little evidence for a specific diagnosable MDMA dependence syndrome because MDMA is typically used relatively infrequently. There are currently no medications to treat MDMA addiction. Harm Assessment A 2007 UK study ranked MDMA 18th in harmfulness out of 20 recreational drugs. Rankings for each drug were based on the risk for acute physical harm, the propensity for physical and psychological dependency on the drug, and the negative familial and societal impacts of the drug. The authors did not evaluate or rate the negative impact of ecstasy on the cognitive health of ecstasy users ( e.g. impaired memory and concentration ). Overdose MDMA overdose symptoms vary widely due to the involvement of multiple organ systems. Some of the more overt overdose symptoms are listed in the table below. The number of instances of fatal MDMA intoxication is low relative to its usage rates. In most fatalities MDMA was not the only drug involved. Acute toxicity is mainly caused by serotonin syndrome and sympathomimetic effects. MDMA 's toxicity in overdose may be exacerbated by caffeine, with which it is frequently cut ( mixed with to increase volume ). A scheme for management of acute MDMA toxicity has been published focusing on treatment of hyperthermia, hyponatraemia, seratonin syndrome, and multiple organ failure. Symptoms of overdose System Minor or moderate overdose Severe overdose Cardiovascular Disseminated intravascular coagulation Intracranial hemorrhage Severe hypertension or hypotension Hypotensive bleeding Central nervous system Abnormally fast reflexes Agitation Mental confusion Paranoia Stimulant psychosis Cognitive and memory impairment potentially to the point of retrograde or anterograde amnesia Coma Convulsions Hallucinations Loss of consciousness Serotonin syndrome Musculoskeletal Muscle rigidity Rhabdomyolysis ( i.e., rapid muscle breakdown ) Respiratory Acute respiratory distress syndrome Urinary Acute kidney injury Other Cerebral edema Hepatitis Hyperpyrexia ( a life - threatening elevation of body temperature ) Hyponatremia ( Syndrome of inappropriate antidiuretic hormone ) Interactions A number of drug interactions can occur between MDMA and other drugs, including serotonergic drugs. MDMA also interacts with drugs which inhibit CYP450 enzymes, like ritonavir ( Norvir ), particularly CYP2D6 inhibitors. Concurrent use of MDMA high dosages with another serotonergic drug can result in a life - threatening condition called serotonin syndrome. Severe overdose resulting in death has also been reported in people who took MDMA in combination with certain monoamine oxidase inhibitors, such as phenelzine ( Nardil ), tranylcypromine ( Parnate ), or moclobemide ( Aurorix, Manerix ). Pharmacology Pharmacodynamics MDMA binds to serotonin transporters. MDMA acts primarily as a presynaptic releasing agent of serotonin, norepinephrine, and dopamine, which arises from its activity at trace amine - associated receptor 1 ( TAAR1 ) and vesicular monoamine transporter 2 ( VMAT2 ). MDMA is a monoamine transporter substrate ( i.e., a substrate for DAT, NET, and SERT ), so it enters monoamine neurons via these neuronal membrane transport proteins ; by acting as a monoamine transporter substrate, MDMA produces competitive reuptake inhibition at the neuronal membrane transporters ( i.e., it competes with endogenous monoamines for reuptake ). MDMA inhibits both vesicular monoamine transporters ( VMATs ), the second of which ( VMAT2 ) is highly expressed within monoamine neurons at vesicular membranes. Once inside a monoamine neuron, MDMA acts as a VMAT2 inhibitor and a TAAR1 agonist. Inhibition of VMAT2 by MDMA results in increased concentrations of the associated neurotransmitter ( serotonin, norepinephrine, or dopamine ) in the cytosol of a monoamine neuron. Activation of TAAR1 by MDMA triggers protein kinase A and protein kinase C signaling events which then phosphorylates the associated monoamine transporters -- DAT, NET, or SERT -- of the neuron. In turn, these phosphorylated monoamine transporters either reverse transport direction -- i.e., move neurotransmitters from the cytosol to the synaptic cleft -- or withdraw into the neuron, respectively producing neurotransmitter efflux and noncompetitive reuptake inhibition at the neuronal membrane transporters. MDMA has ten times more affinity for uptake at serotonin transporters compared to dopamine and norepinephrine transporters and consequently has mainly serotonergic effects. In summary, MDMA enters monoamine neurons by acting as a monoamine transporter substrate. MDMA activity at VMAT2 moves neurotransmitters out from synaptic vesicles and into the cytosol ; MDMA activity at TAAR1 moves neurotransmitters out of the cytosol and into the synaptic cleft. MDMA also has weak agonist activity at postsynaptic serotonin receptors 5 - HT and 5 - HT receptors, and its more efficacious metabolite MDA likely augments this action. Cortisol, prolactin, and oxytocin quantities in serum are increased by MDMA. A placebo - controlled study in 15 human volunteers found 100 mg MDMA increased blood levels of oxytocin, and the amount of oxytocin increase was correlated with the subjective prosocial effects of MDMA. ( S ) - MDMA is more effective in eliciting 5 - HT, NE, and DA release, while ( D ) - MDMA is overall less effective, and more selective for 5 - HT and NE release ( having only a very faint efficacy on DA release ). MDMA is a ligand at both sigma receptor subtypes, though its efficacies at the receptors have not yet been elucidated. Pharmacokinetics Diagram showing the sequence of MDMA metabolization. MDMA reaches maximal concentrations in the blood stream between 1.5 and 3 hours after ingestion. It is then slowly metabolized and excreted, with levels of MDMA and its metabolites decreasing to half their peak concentration over the next several hours. The duration of action of MDMA is usually four to six hours, after which serotonin levels in the brain are depleted. Serotonin levels typically return to normal within 24 -- 48 hours. Metabolites of MDMA that have been identified in humans include 3, 4 - methylenedioxyamphetamine ( MDA ), 4 - hydroxy - 3 - methoxymethamphetamine ( HMMA ), 4 - hydroxy - 3 - methoxyamphetamine ( HMA ), 3, 4 - dihydroxyamphetamine ( DHA ) ( also called alpha - methyldopamine ( α - Me - DA ) ), 3, 4 - methylenedioxyphenylacetone ( MDP2P ), and 3, 4 - Methylenedioxy - N - hydroxyamphetamine ( MDOH ). The contributions of these metabolites to the psychoactive and toxic effects of MDMA are an area of active research. 80 % of MDMA is metabolised in the liver, and about 20 % is excreted unchanged in the urine. MDMA is known to be metabolized by two main metabolic pathways : ( 1 ) O - demethylenation followed by catechol - O - methyltransferase ( COMT ) - catalyzed methylation and / or glucuronide / sulfate conjugation ; and ( 2 ) N - dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. The metabolism may be primarily by cytochrome P450 ( CYP450 ) enzymes CYP2D6 and CYP3A4 and COMT. Complex, nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8, resulting in zeroth order kinetics at higher doses. It is thought that this can result in sustained and higher concentrations of MDMA if the user takes consecutive doses of the drug. MDMA and metabolites are primarily excreted as conjugates, such as sulfates and glucuronides. MDMA is a chiral compound and has been almost exclusively administered as a racemate. However, the two enantiomers have been shown to exhibit different kinetics. The disposition of MDMA may also be stereoselective, with the S - enantiomer having a shorter elimination half - life and greater excretion than the R - enantiomer. Evidence suggests that the area under the blood plasma concentration versus time curve ( AUC ) was two to four times higher for the ( R ) - enantiomer than the ( S ) - enantiomer after a 40 mg oral dose in human volunteers. Likewise, the plasma half - life of ( R ) - MDMA was significantly longer than that of the ( S ) - enantiomer ( 5.8 ± 2.2 hours vs 3.6 ± 0.9 hours ). However, because MDMA excretion and metabolism have nonlinear kinetics, the half - lives would be higher at more typical doses ( 100 mg is sometimes considered a typical dose ). Chemistry ( R ) - MDMA ( S ) - MDMA MDMA is a racemic mixture and exists as two enantiomers : ( R ) - and ( S ) - MDMA. A powdered salt of MDMA Reactors used to synthesize MDMA on an industrial scale in a clandestine chemical factory in Cikande, Indonesia MDMA is in the substituted methylenedioxyphenethylamine and substituted amphetamine classes of chemicals. As a free base, MDMA is a colorless oil insoluble in water. The most common salt of MDMA is the hydrochloride salt ; pure MDMA hydrochloride is water - soluble and appears as a white or off - white powder or crystal. Synthesis There are numerous methods available to synthesize MDMA via different intermediates. The original MDMA synthesis described in Merck 's patent involves brominating safrole to 1 - ( 3, 4 - methylenedioxyphenyl ) - 2 - bromopropane and then reacting this adduct with methylamine. Most illicit MDMA is synthesized using MDP2P ( 3, 4 - methylenedioxyphenyl - 2 - propanone ) as a precursor. MDP2P in turn is generally synthesized from piperonal, safrole or isosafrole. One method is to isomerize safrole to isosafrole in the presence of a strong base, and then oxidize isosafrole to MDP2P. Another method uses the Wacker process to oxidize safrole directly to the MDP2P intermediate with a palladium catalyst. Once the MDP2P intermediate has been prepared, a reductive amination leads to racemic MDMA ( an equal parts mixture of ( R ) - MDMA and ( S ) - MDMA ). Relatively small quantities of essential oil are required to make large amounts of MDMA. The essential oil of Ocotea cymbarum, for example, typically contains between 80 and 94 % safrole. This allows 500 ml of the oil to produce between 150 and 340 grams of MDMA. Synthesis of MDMA from piperonal Synthesis of MDMA and related analogs from safrole Detection in body fluids MDMA and MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDMA or its major metabolites, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10 % those of the parent drug. History Early research and use German patents for MDMA synthesis and the subsequent methylhydrastinine synthesis filed by Merck on 24 December 1912 and issued in 1914. MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch. At the time, Merck was interested in developing substances that stopped abnormal bleeding. Merck wanted to avoid an existing patent held by Bayer for one such compound : hydrastinine. Köllisch developed a preparation of a hydrastinine analogue, methylhydrastinine, at the request of fellow lab members, Walther Beckh and Otto Wolfes. MDMA ( called methylsafrylamin, safrylmethylamin or N - Methyl - a-Methylhomopiperonylamin in Merck laboratory reports ) was an intermediate compound in the synthesis of methylhydrastinine. Merck was not interested in MDMA itself at the time. On 24 December 1912, Merck filed two patent applications that described the synthesis and some chemical properties of MDMA and its subsequent conversion to methylhydrastinine. Merck records indicate its researchers returned to the compound sporadically. A 1920 Merck patent describes a chemical modification to MDMA. In 1927, Max Oberlin studied the pharmacology of MDMA while searching for substances with effects similar to adrenaline or ephedrine, the latter being structurally similar to MDMA. Compared to ephedrine, Oberlin observed that it had similar effects on vascular smooth muscle tissue, stronger effects at the uterus, and no `` local effect at the eye ''. MDMA was also found to have effects on blood sugar levels comparable to high doses of ephedrine. Oberlin concluded that the effects of MDMA were not limited to the sympathetic nervous system. Research was stopped `` particularly due to a strong price increase of safrylmethylamine '', which was still used as an intermediate in methylhydrastinine synthesis. Albert van Schoor performed simple toxicological tests with the drug in 1952, most likely while researching new stimulants or circulatory medications. After pharmacological studies, research on MDMA was not continued. In 1959, Wolfgang Fruhstorfer synthesized MDMA for pharmacological testing while researching stimulants. It is unclear if Fruhstorfer investigated the effects of MDMA in humans. Outside of Merck, other researchers began to investigate MDMA. In 1953 and 1954, the United States Army commissioned a study of toxicity and behavioral effects in animals injected with mescaline and several analogues, including MDMA. Conducted at the University of Michigan in Ann Arbor, these investigations were declassified in October 1969 and published in 1973. A 1960 Polish paper by Biniecki and Krajewski describing the synthesis of MDMA as an intermediate was the first published scientific paper on the substance. MDMA may have been in non-medical use in the western United States in 1968. An August 1970 report at a meeting of crime laboratory chemists indicates MDMA was being used recreationally in the Chicago area by 1970. MDMA likely emerged as a substitute for its analog methylenedioxyamphetamine ( MDA ), a drug at the time popular among users of psychedelics which was made a Schedule 1 substance in the United States in 1970. Shulgin 's research and early use in therapy Alexander and Ann Shulgin in December 2011 American chemist and psychopharmacologist Alexander Shulgin reported he synthesized MDMA in 1965 while researching methylenedioxy compounds at Dow Chemical Company, but did not test the psychoactivity of the compound at this time. Around 1970, Shulgin sent instructions for N - methylated MDA ( MDMA ) synthesis to the founder of a Los Angeles chemical company who had requested them. This individual later provided these instructions to a client in the Midwest. Shulgin may have suspected he played a role in the emergence of MDMA in Chicago. Shulgin first heard of the psychoactive effects of N - methylated MDA around 1975 from a young student who reported `` amphetamine - like content ''. Around 30 May 1976, Shulgin again heard about the effects of N - methylated MDA, this time from a graduate student in a medicinal chemistry group he advised at San Francisco State University who directed him to the University of Michigan study. She and two close friends had consumed 100 mg of MDMA and reported positive emotional experiences. Following the self - trials of a colleague at the University of San Francisco, Shulgin synthesized MDMA and tried it himself in September and October 1976. Shulgin first reported on MDMA in a presentation at a conference in Bethesda, Maryland in December 1976. In 1978, he and David E. Nichols published a report on the drug 's psychoactive effect in humans. They described MDMA as inducing `` an easily controlled altered state of consciousness with emotional and sensual overtones '' comparable `` to marijuana, to psilocybin devoid of the hallucinatory component, or to low levels of MDA ''. While not finding his own experiences with MDMA particularly powerful, Shulgin was impressed with the drug 's disinhibiting effects and thought it could be useful in therapy. Believing MDMA allowed users to strip away habits and perceive the world clearly, Shulgin called the drug `` window ''. Shulgin occasionally used MDMA for relaxation, referring to it as `` my low - calorie martini '', and gave the drug to friends, researchers, and others who he thought could benefit from it. One such person was Leo Zeff, a psychotherapist who had been known to use psychedelic substances in his practice. When he tried the drug in 1977, Zeff was impressed with the effects of MDMA and came out of his semi-retirement to promote its use in therapy. Over the following years, Zeff traveled around the US and occasionally to Europe, eventually training an estimated four thousand psychotherapists in the therapeutic use of MDMA. Zeff named the drug `` Adam '', believing it put users in a state of primordial innocence. Psychotherapists who used MDMA believed the drug eliminated the typical fear response and increased communication. Sessions were usually held in the home of the patient or the therapist. The role therapist was minimized in favor of patient self - discovery accompanied by MDMA induced feelings of empathy. Depression, substance abuse, relationship problems, premenstrual syndrome, and autism were among several psychiatric disorders MDMA assisted therapy was reported to treat. According to psychiatrist George Greer, therapists who used MDMA in their practice were impressed by the results. Anecdotally, MDMA was said to greatly accelerate therapy. Rising recreational use In the late 1970s and early 1980s, `` Adam '' spread through personal networks of psychotherapists, psychiatrists, users of psychedelics, and yuppies. Hoping MDMA could avoid criminalization like LSD and mescaline, psychotherapists and experimenters attempted to limit the spread of MDMA and information about it while conducting informal research. Early MDMA distributors were deterred from large scale operations by the threat of possible legislation. Between the 1970s and the mid-1980s, this network of MDMA users consumed an estimated 500,000 doses. A small recreational market for MDMA developed by the late 1970s, consuming perhaps 10,000 doses in 1976. By the early 1980s MDMA was being used in Boston and New York City nightclubs such as Studio 54 and Paradise Garage. Into the early 1980s, as the recreational market slowly expanded, production of MDMA was dominated by a small group of therapeutically minded Boston chemists. Having commenced production in 1976, this `` Boston Group '' did not keep up with growing demand and shortages frequently occurred. Perceiving a business opportunity, Michael Clegg, the Southwest distributor for the Boston Group, started his own `` Texas Group '' backed financially by Texas friends. In 1981, Clegg had coined `` Ecstasy '' as a slang term for MDMA to increase its marketability. Starting in 1983, the Texas Group mass - produced MDMA in a Texas lab or imported it from California and marketed tablets using pyramid sales structures and toll - free numbers. MDMA could be purchased via credit card and taxes were paid on sales. Under the brand name `` Sassyfras '', MDMA tablets were sold in brown bottles. The Texas Group advertised `` Ecstasy parties '' at bars and discos, describing MDMA as a `` fun drug '' and `` good to dance to ''. MDMA was openly distributed in Austin and Dallas - Fort Worth area bars and nightclubs, becoming popular with yuppies, college students, and gays. Recreational use also increased after several cocaine dealers switched to distributing MDMA following experiences with the drug. A California laboratory that analyzed confidentially submitted drug samples first detected MDMA in 1975. Over the following years the number of MDMA samples increased, eventually exceeding the number of MDA samples in the early 1980s. By the mid-1980s, MDMA use had spread to colleges around the United States. Media attention and scheduling United States 27 July 1984 Federal Register notice of the proposed MDMA scheduling In an early media report on MDMA published in 1982, a Drug Enforcement Administration ( DEA ) spokesman stated the agency would ban the drug if enough evidence for abuse could be found. By mid-1984, MDMA use was becoming more noticed. Bill Mandel reported on `` Adam '' in a 10 June San Francisco Chronicle article, but misidentified the drug as methyloxymethylenedioxyamphetamine ( MMDA ). In the next month, the World Health Organization identified MDMA as the only substance out of twenty phenethylamines to be seized a significant number of times. After a year of planning and data collection, MDMA was proposed for scheduling by the DEA on 27 July 1984 with a request for comments and objections. The DEA was surprised when a number of psychiatrists, psychotherapists, and researchers objected to the proposed scheduling and requested a hearing. In a Newsweek article published the next year, a DEA pharmacologist stated that the agency had been unaware of its use among psychiatrists. An initial hearing was held on 1 February 1985 at the DEA offices in Washington, D.C. with administrative law judge Francis L. Young presiding. It was decided there to hold three more hearings that year : Los Angeles on 10 June, Kansas City, Missouri on 10 -- 11 July, and Washington, D.C. on 8 -- 11 October. Sensational media attention was given to the proposed criminalization and the reaction of MDMA proponents, effectively advertising the drug. In response to the proposed scheduling, the Texas Group increased production from 1985 estimates of 30,000 tablets a month to as many as 8,000 per day, potentially making two million ecstasy tablets in the months before MDMA was made illegal. By some estimates the Texas Group distributed 500,000 tablets per month in Dallas alone. According to one participant in an ethnographic study, the Texas Group produced more MDMA in eighteen months than all other distribution networks combined across their entire histories. By May 1985, MDMA use was widespread in California, Texas, southern Florida, and the northeastern United States. According to the DEA there was evidence of use in twenty - eight states and Canada. Urged by Senator Lloyd Bentsen, the DEA announced an emergency Schedule I classification of MDMA on 31 May 1985. The agency cited increased distribution in Texas, escalating street use, and new evidence of MDA ( an analog of MDMA ) neurotoxicity as reasons for the emergency measure. The ban took effect one month later on 1 July 1985 in the midst of Nancy Reagan 's `` Just Say No '' campaign. As a result of several expert witnesses testifying that MDMA had an accepted medical usage, the administrative law judge presiding over the hearings recommended that MDMA be classified as a Schedule III substance. Despite this, DEA administrator John C. Lawn overruled and classified the drug as Schedule I. Later Harvard psychiatrist Lester Grinspoon sued the DEA, claiming that the DEA had ignored the medical uses of MDMA, and the federal court sided with Grinspoon, calling Lawn 's argument `` strained '' and `` unpersuasive '', and vacated MDMA 's Schedule I status. Despite this, less than a month later Lawn reviewed the evidence and reclassified MDMA as Schedule I again, claiming that the expert testimony of several psychiatrists claiming over 200 cases where MDMA had been used in a therapeutic context with positive results could be dismissed because they were n't published in medical journals. No double blind studies had yet been conducted as to the efficacy of MDMA for therapy. United Nations While engaged in scheduling debates in the United States, the DEA also pushed for international scheduling. In 1985 the World Health Organization 's Expert Committee on Drug Dependence recommended that MDMA be placed in Schedule I of the 1971 United Nations Convention on Psychotropic Substances. The committee made this recommendation on the basis of the pharmacological similarity of MDMA to previously scheduled drugs, reports of illicit trafficking in Canada, drug seizures in the United States, and lack of well - defined therapeutic use. While intrigued by reports of psychotherapeutic uses for the drug, the committee viewed the studies as lacking appropriate methodological design and encouraged further research. Committee chairman Paul Grof dissented, believing international control was not warranted at the time and a recommendation should await further therapeutic data. The Commission on Narcotic Drugs added MDMA to Schedule I of the convention on 11 February 1986. Post-scheduling A 1995 Vibe Tribe rave in Erskineville, New South Wales, Australia being broken up by police. MDMA use spread globally along with rave culture. Play media A 2000 United States Air Force video dramatizing the dangers of MDMA abuse. The use of MDMA in Texas clubs declined rapidly after criminalization, although by 1991 the drug remained popular among young middle - class whites and in nightclubs. In 1985, MDMA use became associated with Acid House on the Spanish island of Ibiza. Thereafter in the late 1980s, the drug spread alongside rave culture to the UK and then to other European and American cities. Illicit MDMA use became increasingly widespread among young adults in universities and later, in high schools. Since the mid-1990s, MDMA has become the most widely used amphetamine - type drug by college students and teenagers. MDMA became one of the four most widely used illicit drugs in the US, along with cocaine, heroin, and cannabis. According to some estimates as of 2004, only marijuana attracts more first time users in the US. After MDMA was criminalized, most medical use stopped, although some therapists continued to prescribe the drug illegally. Later, Charles Grob initiated an ascending - dose safety study in healthy volunteers. Subsequent legally - approved MDMA studies in humans have taken place in the US. in Detroit ( Wayne State University ), Chicago ( University of Chicago ), San Francisco ( UCSF and California Pacific Medical Center ), Baltimore ( NIDA -- NIH Intramural Program ), and South Carolina, as well as in Switzerland ( University Hospital of Psychiatry, Zürich ), the Netherlands ( Maastricht University ), and Spain ( Universitat Autònoma de Barcelona ). `` Molly '', short for ' molecule ', was recognized as a slang term for crystalline or powder MDMA in the 2000s. In 2010, the BBC reported that use of MDMA had decreased in the UK in previous years. This may be due to increased seizures during use and decreased production of the precursor chemicals used to manufacture MDMA. Unwitting substitution with other drugs, such as mephedrone and methamphetamine, as well as legal alternatives to MDMA, such as BZP, MDPV, and methylone, are also thought to have contributed to its decrease in popularity. Society and culture Global estimates of illegal drug users in 2014 ( in millions of users ) Substance Best estimate Low estimate High estimate Amphetamine - type stimulants 35.65 15.34 55.90 Cannabis 182.50 127.54 233.65 Cocaine 18.26 14.88 22.08 Ecstasy 19.40 9.89 29.01 Opiates 17.44 13.74 21.59 Opioids 33.12 28.57 38.52 Legal status MDMA is legally controlled in most of the world under the UN Convention on Psychotropic Substances and other international agreements, although exceptions exist for research and limited medical use. In general, the unlicensed use, sale or manufacture of MDMA are all criminal offences. Australia In Australia, MDMA was declared an illegal substance in 1986 because of its harmful effects and potential for abuse. It is classed as a Schedule 9 Prohibited Substance in the country, meaning it is available for scientific research purposes only. Any other type of sale, use or manufacture is strictly prohibited by law. Permits for research uses on humans must be approved by a recognized ethics committee on human research. In Western Australia under the Misuse of Drugs Act 1981 4.0 g of MDMA is the amount required determining a court of trial, 2.0 g is considered a presumption with intent to sell or supply and 28.0 g is considered trafficking under Australian law. United Kingdom In the United Kingdom, MDMA was made illegal in 1977 by a modification order to the existing Misuse of Drugs Act 1971. Although MDMA was not named explicitly in this legislation, the order extended the definition of Class A drugs to include various ring - substituted phenethylamines. The drug is therefore illegal to sell, buy, or possess the drug without a licence in the UK. Penalties include a maximum of seven years and / or unlimited fine for possession ; life and / or unlimited fine for production or trafficking. Some researchers such as David Nutt have criticized the current scheduling of MDMA, what he determined to be a relatively harmless drug. An editorial he wrote in the Journal of Psychopharmacology, where he compared the risk of harm for horse riding ( 1 adverse event in 350 ) to that of ecstasy ( 1 in 10,000 ) resulted in his dismissal as well as the resignation of his colleagues from the ACMD. United States In the United States, MDMA is currently placed in Schedule I of the Controlled Substances Act. In a 2011 federal court hearing the American Civil Liberties Union successfully argued that the sentencing guideline for MDMA / ecstasy is based on outdated science, leading to excessive prison sentences. Other courts have upheld the sentencing guidelines. The United States District Court for the Eastern District of Tennessee explained its ruling by noting that `` an individual federal district court judge simply can not marshal resources akin to those available to the Commission for tackling the manifold issues involved with determining a proper drug equivalency. '' Netherlands In the Netherlands, the Expert Committee on the List ( Expertcommissie Lijstensystematiek Opiumwet ) issued a report in June 2011 which discussed the evidence for harm and the legal status of MDMA, arguing in favor of maintaining it on List I. Canada In Canada, MDMA is listed as a Schedule 1 as it is an analogue of amphetamine. The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule III to Schedule I in March 2012. Demographics UNODC map showing the use of ecstasy by country in 2014 for the global population aged 15 -- 64. In 2014, 3.5 % of 18 to 25 year - olds had used MDMA in the United States. In Europe, an estimated 37 % of regular club - goers aged 14 to 35 used MDMA in the past year according to the 2015 European Drug report. The highest one - year prevalence of MDMA use in Germany in 2012 was 1.7 % among people aged 25 to 29 compared with a population average of 0.4 %. Among adolescent users in the United States between 1999 and 2008, girls were more likely to use MDMA than boys. Economics Europe In 2008 the European Monitoring Centre for Drugs and Drug Addiction noted that although there were some reports of tablets being sold for as little as € 1, most countries in Europe then reported typical retail prices in the range of € 3 to € 9 per tablet, typically containing 25 -- 65 mg of MDMA. By 2014 the EMCDDA reported that the range was more usually between € 5 and € 10 per tablet, typically containing 57 -- 102 mg of MDMA, although MDMA in powder form was becoming more common. North america The United Nations Office on Drugs and Crime stated in its 2014 World Drug Report that US ecstasy retail prices range from US $ 1 to $70 per pill, or from $15,000 to $32,000 per kilogram. A new research area named Drug Intelligence aims to automatically monitor distribution networks based on image processing and machine learning techniques, in which an Ecstasy pill picture is analyzed to detect correlations among different production batches. These novel techniques allow police scientists to facilitate the monitoring of illicit distribution networks. As of October 2015, most of the MDMA in the United States is produced in British Columbia, Canada and imported by Canada - based Asian transnational criminal organizations. The market for MDMA in the United States is relatively small compared to methamphetamine, cocaine, and heroin. In the United States, about 0.9 million people used ecstasy in 2010. Australia MDMA is particularly expensive in Australia, costing A $ 15 -- A $30 per tablet. In terms of purity data for Australian MDMA, the average is around 34 %, ranging from less than 1 % to about 85 %. The majority of tablets contain 70 -- 85 mg of MDMA. Most MDMA enters Australia from the Netherlands, the UK, Asia, and the US. Corporate logos on pills A number of ecstasy manufacturers brand their pills with a logo, often being a corporate logo, to help distinguish between suppliers ; one of the most notable logos that appears on pills is the Mitsubishi logo. Some pills depict logos of products or shows popular with children, such as Shaun the Sheep. Research See also : List of investigational anxiolytics The Multidisciplinary Association for Psychedelic Studies ( MAPS ) is funding pilot studies and clinical trials investigating the use of MDMA in psychotherapy to treat posttraumatic stress disorder ( PTSD ), social anxiety in autistic adults, and anxiety in terminal illness. In November 2016, the United States Food and Drug Administration ( FDA ) approved large - scale phase 3 clinical trials involving the use of MDMA for the treatment of PTSD in individuals who do not respond to traditional prescription drugs or psychotherapy. MDMA has also been proposed as an adjunct to substance abuse treatment. In 2017, doctors in the UK began the first clinical study of MDMA in alcohol addiction. The potential for MDMA to be used as a rapid - acting antidepressant has been studied in clinical trials, but as of 2017 the evidence on efficacy and safety were insufficient to reach a conclusion. A 2014 review of the safety and efficacy of MDMA as a treatment for various disorders, particularly PTSD, indicated that MDMA has therapeutic efficacy in some patients ; however, it emphasized that issues regarding the control - ability of MDMA - induced experiences and neurochemical recovery must be addressed. The author noted that oxytocin and D - cycloserine are potentially safer co-drugs in PTSD treatment, albeit with limited evidence of efficacy. This review and a second corroborating review by a different author both concluded that, because of MDMA 's demonstrated potential to cause lasting harm in humans ( e.g., serotonergic neurotoxicity and persistent memory impairment ), `` considerably more research must be performed '' on its efficacy in PTSD treatment to determine if the potential treatment benefits outweigh its potential to harm to a patient. Notes Jump up ^ The term MDMA is a contraction of 3, 4 - methylenedioxy - methamphetamine ; it is also known as ecstasy ( shortened to `` E '', `` X '', or `` XTC '' ), mandy, and molly. The international nonproprietary name is midomafetamine. 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Jump up ^ `` Schedule I ''. Controlled Drugs and Substances Act. Isomer Design. Retrieved 9 December 2013. Jump up ^ `` Definitions and interpretations ''. Controlled Drugs and Substances Act. Isomer Design. Retrieved 9 December 2013. Jump up ^ Wu, Ping ; Liu, Xinhua ; Pham, Trang Hoang ; Jin, Jue ; Fan, Bin ; Jin, Zhezhen ( 1 November 2010 ). `` Ecstasy use among US adolescents from 1999 to 2008 ''. Drug and Alcohol Dependence. 112 ( 1 -- 2 ) : 33 -- 38. PMC 2967577. PMID 20570447. doi : 10.1016 / j. drugalcdep. 2010.05. 006. Retrieved 7 October 2015. Jump up ^ European Monitoring Centre for Drugs and Drug Addiction ( 2008 ). Annual report : the state of the drugs problem in Europe ( PDF ). Luxembourg : Office for Official Publications of the European Communities. p. 49. ISBN 978 - 92 - 9168 - 324 - 6. Jump up ^ `` European Drug Report 2014, page 26 '' ( PDF ). Jump up ^ `` Ecstasy - type substances Retail and wholesale prices * and purity levels, by drug, region and country or territory ''. United Nations Office on Drugs and Crime. Archived from the original on 8 December 2015. Retrieved 2 January 2015. Jump up ^ Camargo J, Esseiva P, González F, Wist J, Patiny L ( 30 November 2012 ). `` Monitoring of illicit pill distribution networks using an image collection exploration framework ''. Forensic Science International. 223 ( 1 ) : 298 -- 305. PMID 23107059. doi : 10.1016 / j. forsciint. 2012.10. 004. Retrieved 9 December 2013. Jump up ^ Drugtext -- 10 years of ecstasy and other party drug use in Australia : What have we done and what is there left to do ?. Drugtext.org. Retrieved on 11 June 2011. Archived 9 February 2012 at the Wayback Machine. Jump up ^ `` Erowid MDMA Vault : Images ''. Retrieved 3 March 2016. Jump up ^ Steven B. Karch. ( 2011 ). `` A Historical Review of MDMA '' ( PDF ). The Open Forensic Science Journal. 4 : 20 -- 24. doi : 10.2174 / 1874402801104010020. Archived from the original ( PDF ) on 7 April 2016. Jump up ^ `` Now sick dealers peddle Shaun the Sheep Ecstasy tablets ''. Western Daily Press. Retrieved 3 March 2016. Jump up ^ Danforth, Alicia L. ; Struble, Christopher M. ; Yazar - Klosinski, Berra ; Grob, Charles S. ( March 2015 ). `` MDMA - assisted therapy : A new treatment model for social anxiety in autistic adults ''. Progress in Neuro - Psychopharmacology and Biological Psychiatry. 64 : 237 -- 249. doi : 10.1016 / j. pnpbp. 2015.03. 011. Retrieved 17 April 2015. Jump up ^ Maxmen, Amy. `` Psychedelic Compound in Ecstasy Moves Closer to Approval to Treat PTSD ''. Scientific American. Retrieved 18 May 2017. Jump up ^ Maxmen, Amy. `` Psychedelic compound in ecstasy moves closer to approval to treat PTSD ''. Nature. doi : 10.1038 / nature. 2017.21917. Retrieved 18 May 2017. Jump up ^ Waldman, Ayelet ( 2017 - 01 - 10 ). A Really Good Day : How Microdosing Made a Mega Difference in My Mood, My Marriage, and My Life. Knopf Doubleday Publishing Group. ISBN 9780451494108. Retrieved 18 May 2017. Jump up ^ Lattin, Don ( 19 March 2015 ). `` Patients in ecstasy clinical trial find drug beneficial ''. San Francisco Chronicle. Hearst Corporation. Archived from the original on 24 April 2016. Retrieved 28 April 2016. Jump up ^ Mithoefer, Michael C. ; Grob, Charles S. ; Brewerton, Timothy D. ( 2016 ). `` Novel psychopharmacological therapies for psychiatric disorders : psilocybin and MDMA ''. The Lancet. Psychiatry. 3 ( 5 ) : 481 -- 8. ISSN 2215 - 0374. PMID 27067625. doi : 10.1016 / S2215 - 0366 ( 15 ) 00576 - 3. Jump up ^ Hannah Devlin ( 30 June 2017 ). `` World 's first trials of MDMA to treat alcohol addiction set to begin ''. The Guardian. Jump up ^ Patel, Rachel ; Titheradge, Daniel ( 11 January 2017 ). `` MDMA for the treatment of mood disorder : all talk no substance ? ''. 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External links Find more aboutMDMAat Wikipedia 's sister projects Definitions from Wiktionary Media from Commons News from Wikinews Data from Wikidata MDMA Facts and Statistics National Institute on Drug Abuse Methylenedioxymethamphetamine ( MDMA or ' Ecstasy ' ) drug profile European Monitoring Centre for Drugs and Drug Addiction MDMA - Assisted Psychotherapy Multidisciplinary Association for Psychedelic Studies Recreational uses Recreational drug use Major recreational drugs Depressants Barbiturates Benzodiazepines Carbamates Ethanol ( alcohol ) Alcoholic drinks Beer Wine Gabapentinoids GHB Inhalants Medical Nitrous oxide Hazardous solvents contact adhesives Gasoline nail polish remover Paint thinner Other Freon Kava Nonbenzodiazepines Quinazolinones Opioids Buprenorphine Suboxone Subutex Codeine Desomorphine Krokodil Dextropropoxyphene Darvocet Darvon Fentanyl Diamorphine Heroin Hydrocodone Hydromorphone Dilaudid Methadone Mitragyna speciosa Kratom Morphine Opium Oxycodone / paracetamol Tramadol Stimulants Amphetamine Arecoline Areca Betel Caffeine Coffee Energy drinks Tea Cathinone Khat Cocaine Coca Crack Ephedrine Ephedra MDPV Mephedrone Methamphetamine Methylone Methylphenidate Modafinil Nicotine Tobacco Theobromine Cocoa Chocolate Entactogens 2C series 6 - APB Benzofury AMT MDA MDMA Ecstasy Hallucinogens Psychedelics Bufotenin Psychoactive toads Vilca Yopo DMT Ayahuasca LSA LSD - 25 Mescaline Peruvian torch Peyote San Pedro Psilocybin / Psilocin Psilocybin mushrooms Dissociatives DXM Glaucine Inhalants Nitrous oxide alkyl nitrites poppers amyl nitrite Ketamine MXE Muscimol Amanita muscaria PCP Salvinorin A Salvia divinorum Deliriants Atropine and Scopolamine Atropa belladonna Datura Hyoscyamus niger Mandragora officinarum Dimenhydrinate Diphenhydramine Cannabinoids JWH - 018 THC Cannabis Hashish Hash oil Marijuana Oneirogens Calea zacatechichi Silene capensis Club drugs Cocaine Quaaludes MDMA ( Ecstasy ) Nitrous oxide Poppers Drug culture Cannabis culture 420 Cannabis cultivation Cannabis smoking Head shop Legal history of cannabis in the United States Legality of cannabis Marijuana Policy Project Medical cannabis NORML Cannabis and religion Stoner film Coffee culture Coffee break Coffeehouse Latte art Tea house Drinking culture Bartending Beer culture Beer festival Binge drinking Diethyl ether Drinking games Drinking song Happy hour Hip flask Nightclub Pub Pub crawl Sommelier Sports bar Tailgate party Wine bar Wine tasting Psychedelia Psychonautics Art Drug Era Experience Literature Music Microdosing Therapy Smoking culture Cigarette card Fashion cigarettes Cloud - chasing Loosie Smokeasy Smoking fetishism Tobacco smoking Other Club drug Counterculture of the 1960s Dance party Drug paraphernalia Drug tourism Entheogen Hippie Nootropic Party and play Poly drug use Rave Religion and drugs Self - medication Sex and drugs Whoonga Drug production and trade Drug production Coca production in Colombia Drug precursors Opium production in Afghanistan Rolling meth lab Drug trade Illegal drug trade Colombia Darknet market Drug distribution Beer shop Cannabis shop Liquor store Liquor license Issues with drug use Abuse Date rape drug Impaired driving Drug harmfulness Effects of cannabis Addiction Dependence Prevention Opioid replacement therapy Rehabilitation Responsible use Drug - related crime Fetal alcohol spectrum disorder Long - term effects of cannabis Neurotoxicity Overdose Passive smoking of tobacco or other substances Legality of drug use International 1961 Narcotic Drugs 1971 Psychotropic Substances 1988 Drug Trafficking Council of the European Union decisions on designer drugs State level Drug policy Decriminalization Prohibition Supply reduction Policy reform Demand reduction Drug Policy Alliance Harm reduction Law Enforcement Action Partnership Liberalization Latin America Students for Sensible Drug Policy Transform Drug Policy Foundation Drug policy by country Australia Canada Germany India Netherlands Portugal Slovakia Soviet Union Sweden Switzerland United States Just Say No Office of National Drug Control Policy School district drug policies California Colorado Maryland Virginia Other Arguments for and against drug prohibition Capital punishment for drug trafficking Cognitive liberty Designer drug Drug court Drug possession Drug test Narc Politics of drug abuse War on Drugs Mexican Drug War Plan Colombia Philippine Drug War Zero tolerance Lists of countries by... Alcohol legality Alcohol consumption Anabolic steroid legality Cannabis legality Annual use Lifetime use Cigarette consumption Cocaine legality Cocaine use Methamphetamine legality Opiates use Psilocybin mushrooms legality Salvia legality Empathogens / entactogens Phenylalkyl - amines ( other than cathinones ) Unfused benzene ring : 4 - CAB 4 - FA 4 - FMA 4 - MTA 4, 4 ' - DMAR Ariadne Metaescaline MMA PMA PMEA PMMA Benzodioxine : EDMA Benzodioxoles : Phenethylamine : ( Lophophine ) Amphetamines : ( 2 - Methyl - MDA 2, 3 - MDA 3, 4 - MDA ( tenamfetamine ) 5 - Methyl - MDA 6 - Methyl - MDA DiFMDA DMMDA DMMDA - 2 EIDA MDEA MDMA ( midomafetamine ) MDMOH MDOH MMDA MMDA - 2 MMDMA ) 1 - Phenylbutan - 2 - amines : ( BDB EBDB MBDB ) Phentermines : ( MDMP MDPH ) Benzofurans and dihidrobenzofurans : 5 - APB 5 - APDB 5 - EAPB 5 - MAPB 5 - MAPDB 5 - MBPB 6 - APB 6 - APDB 6 - EAPB 6 - MAPB 6 - MAPDB Indanes : 5 - APDI 5 - MAPDI Indole : 6 - API Naphtalenes : Methamnetamine Naphthylaminopropane Tetralin : 6 - APT Cyclized phenyl - alkylamines Aminoindanes : 5 - IAI AMMI ETAI MDAI MDMAI MMAI NM - 2 - AI TAI Aminotetralins : 6 - CAT MDAT MDMAT Cathinones 3 - MMC 4 - EMC Brephedrone Butylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone Pentylone Tryptamines 4 - Methyl - αET αET αMT Chemical classes Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine Euphoriants μ - Opioid receptor agonists ( opioids ) ( e.g., morphine, heroin, hydrocodone, oxycodone, opium, kratom ) α δ subunit - containing voltage - dependent calcium channels blockers ( gabapentinoids ) ( e.g., gabapentin, pregabalin, phenibut ) AMPA receptor antagonists ( e.g., perampanel ) CB receptor agonists ( cannabinoids ) ( e.g., THC, cannabis ) Dopamine receptor agonists ( e.g., levodopa ) Dopamine releasing agents ( e.g., amphetamine, methamphetamine, MDMA, mephedrone ) Dopamine reuptake inhibitors ( e.g., cocaine, methylphenidate ) GABA receptor positive allosteric modulators ( e.g., barbiturates, benzodiazepines, carbamates, ethanol ( alcohol ) ( alcoholic drink ), inhalants, nonbenzodiazepines, quinazolinones ) GHB ( sodium oxybate ) and analogues Glucocorticoids ( corticosteroids ) ( e.g., dexamethasone, prednisone ) nACh receptor agonists ( e.g., nicotine, tobacco, arecoline, areca nut ) Nitric oxide prodrugs ( e.g., alkyl nitrites ( poppers ) ) NMDA receptor antagonists ( e.g., DXM, ketamine, methoxetamine, nitrous oxide, phencyclidine, inhalants ) Orexin receptor antagonists ( e.g., suvorexant ) See also : Recreational drug use Hallucinogens Psychedelics ( 5 - HT agonists ) Benzofurans 2C - B - FLY 2CBFly - NBOMe 5 - MeO - BFE 5 - MeO - DiBF Bromo - DragonFLY F - 2 F - 22 TFMFly Lyserg ‐ amides 1P - ETH - LAD 1P - LSD 2 - Butyllysergamide 3 - Pentyllysergamide AL - LAD ALD - 52 BU - LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH - LAD IP - LAD LAE - 32 LPD - 824 LSA LSD LSD - Pip LSH LSM - 775 LSZ Methylergometrine Methylisopropyllysergamide Methysergide MLD - 41 PARGY - LAD PRO-LAD Phenethyl ‐ amines 2C - x 2C - B 2C - B - AN 2C - Bn 2C - Bu 2C - C 2C - CN 2C - CP 2C - D 2C - E 2C - EF 2C - F 2C - G 2C - G - 1 2C - G - 2 2C - G - 3 2C - G - 4 2C - G - 5 2C - G - 6 2C - G-N 2C - H 2C - I 2C - iP 2C - N 2C - NH2 2C - O 2C - O - 4 2C - P 2C - Ph 2C - SE 2C - T 2C - T - 2 2C - T - 3 2C - T - 4 2C - T - 5 2C - T - 6 2C - T - 7 2C - T - 8 2C - T - 9 2C - T - 10 2C - T - 11 2C - T - 12 2C - T - 13 2C - T - 14 2C - T - 15 2C - T - 16 2C - T - 17 2C - T - 18 2C - T - 19 2C - T - 20 2C - T - 21 2C - T - 22 2C - T - 22.5 2C - T - 23 2C - T - 24 2C - T - 25 2C - T - 27 2C - T - 28 2C - T - 30 2C - T - 31 2C - T - 32 2C - T - 33 2C - TFE 2C - TFM 2C - YN 2C - V 25x - NBx 25x - NB3OMe 25B - NB3OMe 25C - NB3OMe 25D - NB3OMe 25E - NB3OMe 25H - NB3OMe 25I - NB3OMe 25N - NB3OMe 25P - NB3OMe 25T2 - NB3OMe 25T4 - NB3OMe 25T7 - NB3OMe 25TFM - NB3OMe 25x - NB4OMe 25B - NB4OMe 25C - NB4OMe 25D - NB4OMe 25E - NB4OMe 25H - NB4OMe 25I - NB4OMe 25N - NB4OMe 25P - NB4OMe 25T2 - NB4OMe 25T4 - NB4OMe 25T7 - NB4OMe 25TFM - NB4OMe 25x - NBF 25B - NBF 25C - NBF 25D - NBF 25E - NBF 25H - NBF 25I - NBF 25P - NBF 25T2 - NBF 25T7 - NBF 25TFM - NBF 25x - NBMD 25B - NBMD 25C - NBMD 25D - NBMD 25E - NBMD 25F - NBMD 25H - NBMD 25I - NBMD 25P - NBMD 25T2 - NBMD 25T7 - NBMD 25TFM - NBMD 25x - NBOH 25B - NBOH 25C - NBOH 25CN - NBOH 25D - NBOH 25E - NBOH 25F - NBOH 25H - NBOH 25I - NBOH 25P - NBOH 25T2 - NBOH 25T7 - NBOH 25TFM - NBOH 25x - NBOMe 25B - NBOMe 25C - NBOMe 25CN - NBOMe 25D - NBOMe 25E - NBOMe 25F - NBOMe 25G - NBOMe 25H - NBOMe 25I - NBOMe 25iP - NBOMe 25N - NBOMe 25P - NBOMe 25T2 - NBOMe 25T4 - NBOMe 25T7 - NBOMe 25TFM - NBOMe Atypical structures 25I - NB34MD 2CBCB - NBOMe 2CBFly - NBOMe NBOMe - mescaline 3C - x 3C - AL 3C - BZ 3C - DFE 3C - E 3C - P 4C - x 4C - B 4C - D 4C - T - 2 DOx DOT DOB DOC DOEF DOET DOF DOI DOiPR DOM DON DOPR DOTFM MEM HOT - x HOT - 2 HOT - 7 HOT - 17 MDxx DMMDA DMMDA - 2 Lophophine MDA MMDA MMDA - 2 MMDA - 3a MMDMA Mescaline ( subst. ) 2 - Bromomescaline 3 - TE 4 - TE 3 - TM 4 - TM Allylescaline Asymbescaline Buscaline Cyclopropylmescaline Difluoromescaline Difluoroescaline Escaline Fluoroproscaline Isobuscaline Isoproscaline Jimscaline Mescaline Metaescaline Methallylescaline Proscaline Thioproscaline Trifluoroescaline Trifluoromescaline TMAs TMA TMA - 2 TMA - 3 TMA - 4 TMA - 5 TMA - 6 Others 2C - B - BUTTERFLY 2C - B - DragonFLY 2CB - 5 - hemifly 2 - TOM 5 - TOET 5 - TOM 2CB - Ind 2CD - 5EtO BOB BOD βk - 2C - B βk - 2C - I DESOXY DMCPA DMBMPP DOB - FLY Fenfluramine Ganesha Macromerine MMA TCB - 2 TOMSO Piperazines BZP pFPP Tryptamines alpha - alkyltryptamines 4, 5 - DHP - α - MT 5 - MeO - α - ET 5 - MeO - α - MT α - ET α - MT x - DALT ( Daltocin ) 4 - HO - DALT ( Daltacetin ) 4 - AcO - DALT 5 - MeO - DALT DALT x - DET ( Ethacetin ) 4 - AcO - DET ( Ethocin ) 4 - HO - DET 5 - MeO - DET ( T - 9 ) DET ( Ethocybin ) 4 - PO - DET x - DiPT 1 - Me - 5 - MeO - DiPT ( Ipracetin ) 4 - AcO - DiPT ( Iprocin ) 4 - HO - DiPT ( Foxy Methoxy ) 5 - MeO - DiPT DiPT x - DMT 4, 5 - DHP - DMT 2, N, N - TMT 4 - AcO - DMT 4 - HO - 5 - MeO - DMT 4, N, N - TMT 4 - Propionyloxy - DMT 5, 6 - diBr - DMT 5 - AcO - DMT 5 - Bromo - DMT 5 - MeO - 2, N, N - TMT 5 - MeO - 4, N, N - TMT 5 - MeO - α, N, N - TMT 5 - MeO - DMT 5 - N, N - TMT 7, N, N - TMT α, N, N - TMT ( Bufotenin ) 5 - HO - DMT DMT Norbaeocystin ( Psilocin ) 4 - HO - DMT ( Psilocybin ) 4 - PO - DMT x - DPT ( Depracetin ) 4 - AcO - DPT ( Deprocin ) 4 - HO - DPT 5 - MeO - DPT ( The Light ) DPT Ibogaine - related 18 - MAC 18 - MC Coronaridine Ibogaine Ibogamine ME - 18 - MC Noribogaine Tabernanthine Voacangine x - MET ( Metocin ) 4 - HO - MET ( Metocetin ) 4 - AcO - MET 5 - MeO - MET MET x - MiPT ( Mipracetin ) 4 - AcO - MiPT ( Miprocin ) 4 - HO - MiPT 5 - Me - MiPT ( Moxy ) 5 - MeO - MiPT MiPT Others 4 - HO - DBT 4 - HO - EPT 4 - HO - McPT ( Lucigenol ) 4 - HO - MPMI ( Meprocin ) 4 - HO - MPT 5 - MeO - EiPT 5 - MeO - MALT 5 - MeO - MPMI Aeruginascin Baeocystin DBT DCPT EiPT EPT MPT PiPT Others 5 - MeO - DiBF AL - 38022A ALPHA Dimemebfe Efavirenz Lorcaserin M - ALPHA RH - 34 Also empathogens in general ( e.g. : 5 - APB, 5 - MAPB, 6 - APB and other substituted benzofurans, MDAI, MDMA ). Dissociatives ( NMDAR antagonists ) Arylcyclo ‐ hexylamines Ketamine - related 2 - Fluorodeschloroketamine Arketamine ( ( R ) - ketamine ) Deschloroketamine Ethketamine ( N - Ethylnorketamine ) Esketamine ( ( S ) - ketamine ) Ketamine Methoxetamine Methoxmetamine Methoxyketamine Norketamine Tiletamine PCP - related 3 ' - HO - PCP 3 ' - MeO - PCE 3 ' - MeO - PCMo 3 ' - MeO - PCP BDPC Dieticyclidine ( PCDE ) Eticyclidine ( PCE ) Methoxydine ( 4 ' - MeO - PCP ) PCPr Phencyclidine ( PCP ) Rolicyclidine ( PCPy ) Tenocyclidine ( TCP ) Others BTCP Gacyclidine PRE-084 Diarylethylamines Diphenidine Ephenidine Fluorolintane Methoxphenidine Morphinans Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan Others 2 - EMSB 2 - MDP 8A - PDHQ Aptiganel Budipine Delucemine Dexoxadrol Dizocilpine Etoxadrol Herkinorin Ibogaine Midafotel NEFA Neramexane Nitrous oxide Noribogaine Perzinfotel RB - 64 Remacemide Salvinorin A Selfotel Xenon Deliriants ( mAChR antagonists ) Atropine Benactyzine Benzatropine Benzydamine Biperiden BRN - 1484501 Brompheniramine BZ CAR - 226,086 CAR - 301,060 CAR - 302,196 CAR - 302,282 CAR - 302,368 CAR - 302,537 CAR - 302,668 Chloropyramine Chlorphenamine Clemastine CS - 27349 Cyclizine Cyproheptadine Dicycloverine Dimenhydrinate Diphenhydramine Ditran Doxylamine EA - 3167 EA - 3443 EA - 3580 EA - 3834 Elemicin Flavoxate Hyoscyamine JB - 318 JB - 336 Meclozine Mepyramine Myristicin Orphenadrine Oxybutynin Pheniramine Phenyltoloxamine Procyclidine Promethazine Scopolamine Tolterodine Trihexyphenidyl Tripelennamine Triprolidine WIN - 2299 Others Cannabinoids ( CB agonists ) Natural THC ( Dronabinol ) THCV Synthetic AM - x AM - 087 AM - 251 AM - 279 AM - 281 AM - 356 AM - 374 AM - 381 AM - 404 AM - 411 AM - 630 AM - 661 AM - 678 AM - 679 AM - 694 AM - 735 AM - 855 AM - 881 AM - 883 AM - 905 AM - 906 AM - 919 AM - 926 AM - 938 AM - 1116 AM - 1172 AM - 1220 AM - 1221 AM - 1235 AM - 1241 AM - 1248 AM - 1710 AM - 1714 AM - 1902 AM - 2201 AM - 2212 AM - 2213 AM - 2232 AM - 2233 AM - 2389 AM - 3102 AM - 4030 AM - 4054 AM - 4056 AM - 4113 AM - 6545 CP x CP 47,497 CP 55,244 CP 55,940 ( ± ) - CP 55,940 ( + ) - CP 55,940 ( - ) - CP 55,940 HU - x HU - 210 HU - 211 HU - 239 HU - 243 HU - 308 HU - 320 HU - 331 HU - 336 HU - 345 JWH - x JWH - 007 JWH - 015 JWH - 018 JWH - 019 JWH - 030 JWH - 047 JWH - 048 JWH - 051 JWH - 057 JWH - 073 JWH - 081 JWH - 098 JWH - 116 JWH - 120 JWH - 122 JWH - 133 JWH - 139 JWH - 147 JWH - 148 JWH - 149 JWH - 149 JWH - 161 JWH - 164 JWH - 166 JWH - 167 JWH - 171 JWH - 175 JWH - 176 JWH - 181 JWH - 182 JWH - 184 JWH - 185 JWH - 192 JWH - 193 JWH - 193 JWH - 194 JWH - 195 JWH - 196 JWH - 197 JWH - 198 JWH - 199 JWH - 200 JWH - 203 JWH - 205 JWH - 210 JWH - 210 JWH - 213 JWH - 220 JWH - 229 JWH - 234 JWH - 249 JWH - 250 JWH - 251 JWH - 253 JWH - 258 JWH - 300 JWH - 302 JWH - 307 JWH - 336 JWH - 350 JWH - 359 JWH - 387 JWH - 398 JWH - 424 Misc. designer cannabinoids 4 - HTMPIPO 5F - AB - FUPPYCA 5F - AB - PINACA 5F - ADB 5F - ADB - PINACA 5F - ADBICA 5F - AMB 5F - APINACA 5F - CUMYL - PINACA 5F - NNE1 5F - PB - 22 5F - SDB - 006 A-796,260 A-836,339 AB - 001 AB - 005 AB - CHFUPYCA AB - CHMINACA AB - FUBINACA AB - PINACA ADAMANTYL - THPINACA ADB - CHMINACA ADB - FUBINACA ADB - PINACA ADBICA ADSB - FUB - 187 AMB - FUBINACA APICA APINACA APP - FUBINACA CB - 13 CUMYL - PICA CUMYL - PINACA CUMYL - THPINACA DMHP EAM - 2201 FAB - 144 FDU - PB - 22 FUB - 144 FUB - APINACA FUB - JWH - 018 FUB - PB - 22 FUBIMINA JTE 7 - 31 JTE - 907 Levonantradol MDMB - CHMICA MDMB - CHMINACA MDMB - FUBINACA MEPIRAPIM MAM - 2201 MDA - 19 MN - 18 MN - 25 NESS - 0327 NESS - 040C5 Nabilone Nabitan NM - 2201 NNE1 Org 28611 Parahexyl PTI - 1 PTI - 2 PX - 1 PX - 2 PX - 3 QUCHIC QUPIC RCS - 4 RCS - 8 SDB - 005 SDB - 006 STS - 135 THC - O - acetate THC - O - phosphate THJ - 018 THJ - 2201 UR - 144 WIN 55,212 - 2 XLR - 11 D agonists Apomorphine Aporphine Bromocriptine Cabergoline Lisuride Memantine Nuciferine Pergolide Phenethylamine Piribedil Pramipexole Ropinirole Rotigotine Salvinorin A Also indirect D agonists, such as dopamine reuptake inhibitors ( cocaine, methylphenidate ), releasing agents ( amphetamine, methamphetamine ), and precursors ( levodopa ). GABA enhancers CI - 966 Eszopiclone Ibotenic acid Muscimol ( Amanita muscaria ) Zaleplon Zolpidem Zopiclone Inhalants ( Mixed MOA ) Aliphatic hydrocarbons Butane Gasoline Kerosene Propane Aromatic hydrocarbons Toluene Ethers Diethyl ether Enflurane Haloalkanes Chlorofluorocarbons Chloroform κOR agonists 2 - EMSB Alazocine Bremazocine Butorphan Butorphanol Cyclazocine Cyclorphan Cyprenorphine Diprenorphine Enadoline Herkinorin Heroin HZ - 2 Ibogaine Ketazocine Levallorphan Levomethorphan Levorphanol LPK - 26 Metazocine Morphine Nalbuphine Nalmefene Nalorphine Noribogaine Oxilorphan Pentazocine Phenazocine Proxorphan Racemethorphan Racemorphan Salvinorin A Spiradoline Tifluadom U-50488 U-69,593 Xorphanol Others Glaucine Isoaminile Noscapine Pukateine Stimulants Adamantanes Adapromine Amantadine Bromantane Memantine Rimantadine Adenosine antagonists 8 - Chlorotheophylline 8 - Cyclopentyltheophylline 8 - Phenyltheophylline Aminophylline Caffeine CGS - 15943 Dimethazan Paraxanthine SCH - 58261 Theobromine Theophylline Alkylamines Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane Ampakines CX - 516 CX - 546 CX - 614 CX - 691 CX - 717 IDRA - 21 LY - 404,187 LY - 503,430 Nooglutyl Org 26576 PEPA S - 18986 Sunifiram Unifiram Arylcyclohexylamines Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine Benzazepines 6 - Br - APB SKF - 77434 SKF - 81297 SKF - 82958 Cholinergics A-84,543 A-366,833 ABT - 202 ABT - 418 AR - R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS - 21 Ispronicline Nicotine PHA - 543,613 PNU - 120,596 PNU - 282,987 Pozanicline Rivanicline Sazetidine A SIB - 1553A SSR - 180,711 TC - 1698 TC - 1827 TC - 2216 Tebanicline UB - 165 Varenicline WAY - 317,538 Convulsants Anatoxin - a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil CRL - 40,940 CRL - 40,941 Fluorenol JZ - IV - 10 Modafinil Oxazolines 4 - Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines 1 - ( 4 - Methylphenyl ) - 2 - aminobutane 1 - Methylamino - 1 - ( 3, 4 - methylenedioxyphenyl ) propane 2 - Fuoroamphetamine 2 - Fuoromethamphetamine 2 - OH - PEA 2 - Phenyl - 3 - aminobutane 2, 3 - MDA 3 - Fuoroamphetamine 3 - Fluoroethamphetamine 3 - Fluoromethcathinone 3 - Methoxyamphetamine 3 - Methylamphetamine 3, 4 - DMMC 4 - BMC 4 - CMC 4 - Ethylamphetamine 4 - Fluoroamphetamine 4 - Fluoromethamphetamine 4 - MA 4 - Methylbuphedrone 4 - Methylcathinone 4 - MMA 4 - Methylpentedrone 4 - MTA 6 - FNE AL - 1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine 2 - Amino - 1, 2 - dihydronaphthalene 2 - Aminoindane 5 - ( 2 - Aminopropyl ) indole 2 - Aminotetralin Acridorex Amphetamine ( Dextroamphetamine, Levoamphetamine ) Amphetaminil Arbutamine β - Methylphenethylamine β - Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH 3 - Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D - Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA ( Dextrodopa, Levodopa ) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine ( Dexfenfluramine, Levofenfluramine ) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4 - Hydroxyamphetamine 5 - Iodo - 2 - aminoindane Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L - Deprenyl ( Selegiline ) Lefetamine Lisdexamfetamine Lophophine MBDB MDA ( tenamfetamine ) MDBU MDEA MDMA ( midomafetamine ) MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine ( Dextromethamphetamine, Levomethamphetamine ) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N, alpha - Diethylphenylethylamine N - Ethylbuphedrone N - Ethylhexedrone N, N - Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L - Norpseudoephedrine Octopamine ( drug ) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol ( Levosalbutamol ) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine Phenylmorpholines 3 - Fluorophenmetrazine Fenbutrazate Fenmetramide G - 130 Manifaxine Morazone Morforex Oxaflozane PD - 128,907 Phendimetrazine Phenmetrazine 2 - Phenyl - 3, 6 - dimethylmorpholine Pseudophenmetrazine Radafaxine Piperazines 2C - B - BZP 3C - PEP BZP CM156 DBL - 583 GBR - 12783 GBR - 12935 GBR - 13069 GBR - 13098 GBR - 13119 MeOPP MBZP oMPP Vanoxerine Piperidines 1 - Benzyl - 4 - ( 2 - ( diphenylmethoxy ) ethyl ) piperidine 2 - Benzylpiperidine 2 - Methyl - 3 - phenylpiperidine 3, 4 - Dichloromethylphenidate 4 - Benzylpiperidine 4 - Fluoromethylphenidate 4 - Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate Methylphenidate ( Dexmethylphenidate ) Nocaine Phacetoperane Pipradrol Propylphenidate SCH - 5472 Pyrrolidines 2 - Diphenylmethylpyrrolidine 5 - DBFPV α - PPP α - PBP α - PHP α - PVP α - PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone Racetams Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide Tropanes 4 - fluorotropacocaine 4 ' - Fluorococaine Altropane ( IACFT ) Brasofensine CFT ( WIN 35,428 ) β - CIT ( RTI - 55 ) Cocaethylene Cocaine Dichloropane ( RTI - 111 ) Difluoropine FE - β - CPPIT FP - β - CPPIT Ioflupane ( I ) Norcocaine PIT PTT RTI - 31 RTI - 32 RTI - 51 RTI - 112 RTI - 113 RTI - 120 RTI - 121 ( IPCIT ) RTI - 126 RTI - 150 RTI - 177 RTI - 229 RTI - 336 RTI - 354 RTI - 371 RTI - 386 Salicylmethylecgonine Tesofensine Troparil ( β - CPT, WIN 35,065 - 2 ) Tropoxane WF - 23 WF - 33 Tryptamines 4 - HO - αMT 4 - Methyl - αET 4 - Methyl - αMT 5 - Chloro - αMT 5 - Fluoro - αMT 5 - MeO - αET 5 - MeO - αMT 5 - MeO - DIPT 6 - Fluoro - αMT 7 - Methyl - αET αET αMT Others 2 - MDP 3, 3 - Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D - 161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI - 52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ - 7925476 Lazabemide Leptacline Lomevactone LR - 5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O - 2172 Oxaprotiline PNU - 99,194 PRC200 - SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH - 232 Yohimbine ATC code : N06B Pharmacodynamics Monoamine neurotoxins Adrenergic DSP - 4 Oxidopamine ( 6 - OHDA ) Dopaminergic Fenpropathrin Methamphetamine MPP MPTP Norsalsolinol Oxidopamine ( 6 - OHDA ) Rotenone Serotonergic 3 - CA 4 - CAB 5, 7 - DHT α - Me - DA ( 3, 4 - DHA ) αET αMT DCA MDA ( tenamfetamine ) MDMA ( midomafetamine ) PBA PCA PIA See also : Receptor / signaling modulators Adrenergics Dopaminergics Melatonergics Serotonergics Monoamine reuptake inhibitors Monoamine releasing agents Monoamine metabolism modulators Monoamine releasing agents DRAs Morpholines : Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine Oxazolines : 4 - MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines : 2 - OH - PEA 4 - CAB 4 - FA 4 - FMA 4 - MA 4 - MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine ( Dextroamphetamine Levoamphetamine ) Amphetaminil β - Me - PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D - Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4 - Hydroxyamphetamine Iofetamine ( 123I ) Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA ( tenamfetamine ) MDEA MDMA ( midomafetamine ) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine Piperazines : 2C - B - BZP BZP MBZP MDBZP MeOPP oMPP Others : 2 - ADN 2 - AI 2 - AT 4 - BP 5 - APDI 5 - IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine Levopropylhexedrine NRAs Morpholines : Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine Oxazolines : 4 - MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines : 2 - OH - PEA 4 - CAB 4 - FA 4 - FMA 4 - MA 4 - MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β - Me - PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4 - Hydroxyamphetamine 5 - APDI ( IAP ) 5 - MAPDI ( IMP ) Iofetamine ( 123I ) Lisdexamfetamine Lophophine MBDB MDA ( tenamfetamine ) MDEA MDMA ( midomafetamine ) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline ( also D - Deprenyl ) Tiflorex Tyramine Xylopropamine Zylofuramine Piperazines : 2C - B - BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP Others : 2 - ADN 2 - AI 2 - AT 2 - BP 4 - BP 5 - IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine ( Levopropylhexedrine ) Tuaminoheptane SRAs Aminoindanes : 5 - IAI AMMI ETAI MDAI MDMAI MMAI TAI Aminotetralins : 6 - CAT 8 - OH - DPAT MDAT MDMAT Oxazolines : 4 - Methylaminorex Aminorex Clominorex Fluminorex Phenethylamines : 2 - Methyl - MDA 4 - CAB 4 - FA 4 - FMA 4 - HA 4 - MTA 5 - APDB 5 - Methyl - MDA 6 - APDB 6 - Methyl - MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP IMP Iofetamine Levofenfluramine Lophophine MBDB MDA ( tenamfetamine ) MDEA MDHMA MDMA ( midomafetamine ) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDMA MMMA NAP Norfenfluramine 4 - TFMA pBA pCA pIA PMA PMEA PMMA TAP Piperazines : 2C - B - BZP 3 - MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP Tryptamines : 4 - Methyl - αET 4 - Methyl - αMT 5 - CT 5 - MeO - αET 5 - MeO - αMT 5 - MT αET αMT DMT Tryptamine Others : Indeloxazine Viqualine Others Monoamine activity enhancers : BPAP PPAP DAT modulators : Agonist - like : SoRI - 9804 SoRI - 20040 ; Antagonist - like : SoRI - 20041 Adrenergic release blockers : Bethanidine Bretylium Guanadrel Guanazodine Guanethidine Guanoxan See also : Receptor / signaling modulators Monoamine reuptake inhibitors Adrenergics Dopaminergics Serotonergics Monoamine metabolism modulators Monoamine neurotoxins Serotonin receptor modulators 5 - HT 5 - HT Agonists : 8 - OH - DPAT Adatanserin Amphetamine Antidepressants ( e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine ) Atypical antipsychotics ( e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone ) Azapirones ( e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone ) Bay R 1531 Befiradol BMY - 14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines ( e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine ( methylergonovine ), methysergide, pergolide ) F - 11461 F - 12826 F - 13714 F - 14679 F - 15063 F - 15599 Flesinoxan Flibanserin Flumexadol Lesopitron LY - 293284 LY - 301317 mCPP MKC - 242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU - 24969 S - 14506 S - 14671 S - 15535 Sarizotan Serotonin ( 5 - HT ) SSR - 181507 Sunepitron Tryptamines ( e.g., 5 - CT, 5 - MeO - DMT, 5 - MT, bufotenin, DMT, indorenate, N - Me - 5 - HT, psilocin, psilocybin ) TGBA01AD U-92016A Urapidil Vilazodone Xaliproden Yohimbine Antagonists : Atypical antipsychotics ( e.g., iloperidone, risperidone, sertindole ) AV965 Beta blockers ( e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol ) BMY - 7378 CSP - 2503 Dotarizine Ergolines ( e.g., metergoline ) Flopropione GR - 46611 Isamoltane Lecozotan Mefway Metitepine ( methiothepin ) MIN - 117 ( WF - 516 ) MPPF NAN - 190 Robalzotan S - 15535 SB - 649915 SDZ 216 - 525 Spiperone Spiramide Spiroxatrine UH - 301 WAY - 100135 WAY - 100635 Xylamidine Unknown / unsorted : Acetryptine Ergolines ( e.g., ergometrine ( ergonovine ) ) 5 - HT Agonists : CGS - 12066A CP - 93129 CP - 94253 CP - 122,288 CP - 135807 Eltoprazine Ergolines ( e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine ( methylergonovine ), methysergide, pergolide ) mCPP RU - 24969 Serotonin ( 5 - HT ) Triptans ( e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan ) TFMPP Tryptamines ( e.g., 5 - BT, 5 - CT, 5 - MT, DMT ) Vortioxetine Antagonists : AR - A000002 Beta blockers ( e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol ) Elzasonan Ergolines ( e.g., metergoline ) GR - 127935 Isamoltane LY - 393558 Metitepine ( methiothepin ) SB - 216641 SB - 224289 SB - 236057 Yohimbine Unknown / unsorted : Ergolines ( e.g., cabergoline, ergometrine ( ergonovine ), lisuride ) 5 - HT Agonists : CP - 122,288 CP - 135807 CP - 286601 Ergolines ( e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide ) GR - 46611 L - 694247 L - 772405 mCPP PNU - 109291 PNU - 142633 Serotonin ( 5 - HT ) TGBA01AD Triptans ( e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan ) Tryptamines ( e.g., 5 - BT, 5 - CT, 5 - Et - DMT, 5 - MT, 5 - ( nonyloxy ) tryptamine, DMT ) Antagonists : Alniditan BRL - 15572 Elzasonan Ergolines ( e.g., metergoline ) GR - 127935 Ketanserin LY - 310762 LY - 367642 LY - 393558 LY - 456219 LY - 456220 Metitepine ( methiothepin ) Mianserin Ritanserin Yohimbine Ziprasidone Unknown / unsorted : Acetryptine Ergolines ( e.g., lisuride, lysergol, pergolide ) 5 - HT Agonists : BRL - 54443 Ergolines ( e.g., methysergide ) Serotonin ( 5 - HT ) Triptans ( e.g., eletriptan ) Tryptamines ( e.g., tryptamine ) Antagonists : Metitepine ( methiothepin ) Unknown / unsorted : Ergolines ( e.g., ergometrine ( ergonovine ), lysergol, methylergometrine ( methylergonovine ) 5 - HT Agonists : BRL - 54443 CP - 122,288 Ergolines ( e.g., bromocriptine, lysergol, methylergometrine ( methylergonovine ) methysergide ) Lasmiditan LY - 334370 Serotonin ( 5 - HT ) Triptans ( e.g., eletriptan, naratriptan, sumatriptan ) Tryptamines ( e.g., 5 - MT ) Antagonists : Mianserin Metitepine ( methiothepin ) 5 - HT 5 - HT Agonists : 25H / NB series ( e.g., 25I - NBF, 25I - NBMD, 25I - NBOH, 25I - NBOMe, 25B - NBOMe, 25C - NBOMe, 25TFM - NBOMe, 2CBCB - NBOMe, 25CN - NBOH, 2CBFly - NBOMe ) 2Cs ( e.g., 2C - B, 2C - E, 2C - I, 2C - T - 2, 2C - T - 7, 2C - T - 21 ) 2C - B - FLY 2CB - Ind 5 - Methoxytryptamines ( 5 - MeO - DET, 5 - MeO - DiPT, 5 - MeO - DMT, 5 - MeO - DPT, 5 - MT ) α - Alkyltryptamines ( e.g., 5 - Cl - αMT, 5 - Fl - αMT, 5 - MeO - αET, 5 - MeO - αMT, α - Me - 5 - HT, αET, αMT ) AL - 34662 AL - 37350A Bromo - DragonFLY Dimemebfe DMBMPP DOx ( e.g., DOB, DOC, DOI, DOM ) Efavirenz Ergolines ( e.g., 1P - LSD, ALD - 52, bromocriptine, cabergoline, ergine ( LSA ), ergometrine ( ergonovine ), ergotamine, lisuride, LA - SS - Az, LSB, LSD, LSD - Pip, LSH, LSP, methylergometrine ( methylergonovine ), pergolide ) Flumexadol Jimscaline Lorcaserin MDxx ( e.g., MDA ( tenamfetamine ), MDMA ( midomafetamine ), MDOH, MMDA ) O - 4310 Oxaflozane PHA - 57378 PNU - 22394 PNU - 181731 RH - 34 Phenethylamines ( e.g., lophophine, mescaline ) Piperazines ( e.g., BZP, quipazine, TFMPP ) Serotonin ( 5 - HT ) TCB - 2 TFMFly Tryptamines ( e.g., 5 - BT, 5 - CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine ) Antagonists : 5 - I - R91150 5 - MeO - NBpBrT AC - 90179 Adatanserin Altanserin Antihistamines ( e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine ) AMDA Atypical antipsychotics ( e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine ) Cinanserin CSP - 2503 Deramciclane Dotarizine Eplivanserin Ergolines ( e.g., amesergide, LY - 53857, LY - 215840, mesulergine, metergoline, methysergide, sergolexole ) Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML - 010 Landipirdine LY - 393558 mCPP Medifoxamine Metitepine ( methiothepin ) MIN - 101 MIN - 117 ( WF - 516 ) Naftidrofuryl Nantenine Nelotanserin Opiranserin ( VVZ - 149 ) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin S - 14671 Sarpogrelate Serotonin antagonists and reuptake inhibitors ( e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone ) SR - 46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants ( e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine ) Tricyclic antidepressants ( e.g., amitriptyline ) Typical antipsychotics ( e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine ) Volinanserin Xylamidine Yohimbine Unknown / unsorted : Ergolines ( e.g., dihydroergotamine, nicergoline ) 5 - HT Agonists : 4 - Methylaminorex Aminorex Amphetamines ( e.g., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine ) BW - 723C86 DOx ( e.g., DOB, DOC, DOI, DOM ) Ergolines ( e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine ( methylergonovine ), methysergide, pergolide ) Lorcaserin MDxx ( e.g., MDA ( tenamfetamine ), MDMA ( midomafetamine ), MDOH, ( MMDA ( drug ) Antagonists : Agomelatine Atypical antipsychotics ( e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N - desalkylquetiapine ( norquetiapine ), N - desmethylclozapine ( norclozapine ), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone ) Cyproheptadine EGIS - 7625 Ergolines ( e.g., amesergide, bromocriptine, lisuride, LY - 53857, LY - 272015, mesulergine ) Ketanserin LY - 393558 mCPP Metadoxine Metitepine ( methiothepin ) Pirenperone Pizotifen Propranolol PRX - 08066 Rauwolscine Ritanserin RS - 127445 Sarpogrelate SB - 200646 SB - 204741 SB - 206553 SB - 215505 SB - 221284 SB - 228357 SDZ SER - 082 Tegaserod Tetracyclic antidepressants ( e.g., amoxapine, mianserin, mirtazapine ) Trazodone Typical antipsychotics ( e.g., chlorpromazine ) TIK - 301 Yohimbine Unknown / unsorted : Ergolines ( e.g., ergometrine ( ergonovine ) ) 5 - HT Agonists : 2Cs ( e.g., 2C - B, 2C - E, 2C - I, 2C - T - 2, 2C - T - 7, 2C - T - 21 ) 5 - Methoxytryptamines ( 5 - MeO - DET, 5 - MeO - DiPT, 5 - MeO - DMT, 5 - MeO - DPT, 5 - MT ) α - Alkyltryptamines ( e.g., 5 - Cl - αMT, 5 - Fl - αMT, 5 - MeO - αET, 5 - MeO - αMT, α - Me - 5 - HT, αET, αMT ) A-372159 AL - 38022A Alstonine CP - 809101 Dimemebfe DOx ( e.g., DOB, DOC, DOI, DOM ) Ergolines ( e.g., ALD - 52, cabergoline, dihydroergotamine, ergine ( LSA ), ergotamine, lisuride, LA - SS - Az, LSB, LSD, LSD - Pip, LSH, LSP, pergolide ) Flumexadol Lorcaserin MDxx ( e.g., MDA ( tenamfetamine ), MDMA ( midomafetamine ), MDOH, MMDA ) MK - 212 Org 12962 Org 37684 Oxaflozane PHA - 57378 Phenethylamines ( e.g., lophophine, mescaline ) Piperazines ( e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP ) PNU - 22394 PNU - 181731 Ro60 - 0175 Ro60 - 0213 Serotonin ( 5 - HT ) Tryptamines ( e.g., 5 - BT, 5 - CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine ) Vabicaserin WAY - 629 WAY - 161503 YM - 348 Antagonists : Adatanserin Agomelatine Atypical antipsychotics ( e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine ) Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines ( e.g., amesergide, bromocriptine, LY - 53857, LY - 215840, mesulergine, metergoline, methysergide, sergolexole ) Etoperidone Fluoxetine FR - 260010 Irindalone Ketanserin Ketotifen Latrepirdine ( dimebolin ) Medifoxamine Metitepine ( methiothepin ) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS - 102221 S - 14671 SB - 200646 SB - 206553 SB - 221284 SB - 228357 SB - 242084 SB - 243213 SDZ SER - 082 Tedatioxetine Tetracyclic antidepressants ( e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine ) TIK - 301 Tramadol Trazodone Tricyclic antidepressants ( e.g., amitriptyline, nortriptyline ) Typical antipsychotics ( e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine ) Xylamidine Unknown / unsorted : Efavirenz Ergolines ( e.g., ergometrine ( ergonovine ), methylergometrine ( methylergonovine ) ) 5 - HT 5 - HT Agonists : Alcohols ( e.g., butanol, ethanol ( alcohol ), trichloroethanol ) m - CPBG Phenylbiguanide Piperazines ( e.g., BZP, mCPP, quipazine ) RS - 56812 Serotonin ( 5 - HT ) SR - 57227 SR - 57227A Tryptamines ( e.g., 2 - Me - 5 - HT, 5 - CT, bufotenidine ( 5 - HTQ ) ) Volatiles / gases ( e.g., halothane, isoflurane, toluene, trichloroethane ) YM - 31636 Antagonists : Alosetron AS - 8112 Atypical antipsychotics ( e.g., clozapine, olanzapine, quetiapine ) Azasetron Batanopride Bemesetron ( MDL - 72222 ) Bupropion Cilansetron CSP - 2503 Dazopride Dolasetron Galanolactone Granisetron Hydroxybupropion ICS - 205930 Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants ( e.g., amoxapine, mianserin, mirtazapine ) Thujone Tropanserin Tropisetron Typical antipsychotics ( e.g., loxapine ) Volatiles / gases ( e.g., nitrous oxide, sevoflurane, xenon ) Vortioxetine Zacopride Zatosetron Unknown / unsorted : LY - 53857 Piperazines ( e.g., naphthylpiperazine ) 5 - HT Agonists : 5 - MT BIMU8 Capeserod Cinitapride Cisapride CJ - 033466 Dazopride Metoclopramide Minesapride Mosapride Prucalopride PRX - 03140 Renzapride RS - 67333 RS - 67506 Serotonin ( 5 - HT ) Tegaserod Velusetrag Zacopride Antagonists : GR - 113808 GR - 125487 L - Lysine Piboserod RS - 39604 RS - 67532 SB - 203186 SB - 204070 5 - HT Agonists : Ergolines ( e.g., 2 - Br - LSD ( BOL - 148 ), ergotamine, LSD ) Serotonin ( 5 - HT ) Tryptamines ( e.g., 5 - CT ) Valerenic Acid Antagonists : Asenapine Latrepirdine ( dimebolin ) Metitepine ( methiothepin ) Ritanserin SB - 699551 Unknown / unsorted : Ergolines ( e.g., metergoline, methysergide ) Piperazines ( e.g., naphthylpiperazine ) 5 - HT Agonists : Ergolines ( e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide ) Serotonin ( 5 - HT ) Tryptamines ( e.g., 2 - Me - 5 - HT, 5 - BT, 5 - CT, 5 - MT, Bufotenin, E-6801, E-6837, EMD - 386088, EMDT, LY - 586713, N - Me - 5 - HT, tryptamine ) WAY - 181187 WAY - 208466 Antagonists : ABT - 354 Atypical antipsychotics ( e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone ) AVN - 101 AVN - 211 AVN - 322 AVN - 397 BGC20 - 760 BVT - 5182 BVT - 74316 Cerlapirdine EGIS - 12233 GW - 742457 Idalopirdine Ketanserin Landipirdine Latrepirdine ( dimebolin ) Metitepine ( methiothepin ) MS - 245 PRX - 07034 Ritanserin Ro 04 - 6790 Ro 63 - 0563 SB - 258585 SB - 271046 SB - 357134 SB - 399885 SB - 742457 Tetracyclic antidepressants ( e.g., amoxapine, mianserin ) Tricyclic antidepressants ( e.g., amitriptyline, clomipramine, doxepin, nortriptyline ) Typical antipsychotics ( e.g., chlorpromazine, loxapine ) Unknown / unsorted : Ergolines ( e.g., 2 - Br - LSD ( BOL - 148 ), bromocriptine, lergotrile, pergolide ) Piperazines ( e.g., naphthylpiperazine ) 5 - HT Agonists : 8 - OH - DPAT AS - 19 Bifeprunox E-55888 Ergolines ( e.g., LSD ) LP - 12 LP - 44 RU - 24969 Sarizotan Serotonin ( 5 - HT ) Triptans ( e.g., frovatriptan ) Tryptamines ( e.g., 5 - CT, 5 - MT, bufotenin, N - Me - 5 - HT ) Antagonists : Atypical antipsychotics ( e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine ) Butaclamol DR - 4485 EGIS - 12233 Ergolines ( e.g., 2 - Br - LSD ( BOL - 148 ), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY - 53857, LY - 215840, mesulergine, metergoline, methysergide, sergolexole ) JNJ - 18038683 Ketanserin LY - 215840 Metitepine ( methiothepin ) Ritanserin SB - 258719 SB - 258741 SB - 269970 SB - 656104 SB - 656104A SB - 691673 SLV - 313 SLV - 314 Spiperone SSR - 181507 Tetracyclic antidepressants ( e.g., amoxapine, maprotiline, mianserin, mirtazapine ) Tricyclic antidepressants ( e.g., amitriptyline, clomipramine, imipramine ) Typical antipsychotics ( e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide ) Vortioxetine Unknown / unsorted : Ergolines ( e.g., lisuride, pergolide ) Piperazines ( e.g., naphthylpiperazine ) See also : Receptor / signaling modulators Adrenergics Dopaminergics Melatonergics Monoamine reuptake inhibitors and releasing agents Monoamine metabolism modulators Monoamine neurotoxins Sigma receptor modulators σ Agonists : 3 - PPP 4 - PPBP 5 - MeO - DMT Alazocine ( SKF - 10047 ) Amantadine ANAVEX2 - 73 Arketamine BD - 737 BD - 1052 Captodiame Citalopram CGRP Cloperastine Cocaine Cutamesine ( SA - 4503 ) Cyclazocine Dehydroepiandrosterone ( DHEA ) ( prasterone ) Dehydroepiandrosterone sulfate ( DHEA - S ) ( prasterone sulfate ) Dextrallorphan Dextromethorphan ( DXM ) Dextrorphan ( DXO ) Dimemorfan Dimethyltryptamine ( DMT ) Ditolylguanidine ( DTG ) Donepezil Eliprodil Escitalopram Fabomotizole ( afobazole ) Fluoxetine Fluvoxamine Ifenprodil Igmesine ( JO - 1784 ) IPAB Ketamine L - 687384 MDMA ( midomafetamine ) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC - 14523 Opipramol Pentazocine Pentoxyverine ( carbetapentane ) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan ( methorphan ) Racemorphan ( morphanol ) UMB - 23 UMB - 82 Antagonists : 3 - PPP AC - 927 BD - 1008 BD - 1031 BD - 1047 BD - 1060 BD - 1063 BD - 1067 BMY - 14802 ( BMS - 181100 ) CM - 156 Dup - 734 E-5842 E-52862 ( S1RA ) Haloperidol LR - 132 LR - 172 MS - 377 NE - 100 NPC - 16377 Panamesine ( EMD - 57455 ) PD - 144418 Pentazocine Progesterone Rimcazole ( BW - 234U ) Sertraline SR - 31742A Allosteric modulators : Phenytoin ; Positive : Methylphenylpiracetam SOMCL - 668 Unknown / unsorted : 3 - Methoxydextrallorphan 3 - MeO - PCP 4C - T - 2 4 - IBP 4 - IPBS 4 - MeO - PCP 5 - MeO - DALT 5 - MeO - DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D - Deprenyl DiPT DPT Ibogaine Imipramine KCR - 12 - 83.1 Nemonapride Noribogaine RHL - 033 RS - 67,333 RTI - 55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W - 18 YKP10A σ Agonists : 3 - PPP Arketamine BD - 1047 BD1063 Ditolylguanidine ( DTG ) DKR - 1005 DKR - 1051 Haloperidol Ifenprodil Ketamine MDMA ( midomafetamine ) Methamphetamine OPC - 14523 Opipramol PB - 28 Phencyclidine Siramesine ( Lu 28 - 179 ) UKH - 1114 Antagonists : AC - 927 BD - 1008 BD - 1067 CM - 156 CT - 1812 LR - 172 MIN - 101 Panamesine ( EMD - 57455 ) SAS - 0132 Unknown / unsorted : 3 - Methoxydextrallorphan 3 - MeO - PCE 4 - MeO - PCP 5 - MeO - DALT 5 - MeO - DiPT Clemastine DiPT DPT Ibogaine Nemonapride Nepinalone Noribogaine Pentazocine RS - 67,333 Safinamide TMA UMB - 23 UMB - 82 W - 18 Unsorted Agonists : Berberine Ethylketazocine Fourphit Metaphit Nalbuphine Naluzotan Tapentadol Tenocyclidine Antagonists : AHD1 AZ66 Lamotrigine Naloxone SM - 21 UMB - 100 UMB - 101 UMB - 103 UMB - 116 YZ - 011 YZ - 069 YZ - 185 Allosteric modulators : SKF - 83959 Unknown / unsorted : 18 - Methoxycoronaridine BMY - 13980 Butaclamol Caramiphen Carvotroline Chlorphenamine ( chlorpheniramine ) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD - 59983 Hypericin ( St. John 's wort ) Fluphenazine Gevotroline ( WY - 47384 ) Mepyramine ( pyrilamine ) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR - 31747A Tiospirone ( BMY - 13859 ) Venlafaxine See also : Receptor / signaling modulators Human trace amine - associated receptor ligands TAAR1 Agonists Endogenous Classical monoamine neurotransmitters Dopamine Histamine Norepinephrine Serotonin Trace amines 3 - Iodothyronamine 3 - Methoxytyramine N - Methylphenethylamine N - Methyltyramine m - Octopamine p - Octopamine Phenethylamine Phenylethanolamine Synephrine Tryptamine m - Tyramine p - Tyramine Synthetic Amphetamine DOB DOET 4 - Hydroxyamphetamine Isoprenaline MDA ( tenamfetamine ) MDMA ( midomafetamine ) 2 - Methylphenethylamine 3 - Methylphenethylamine 4 - Methylphenethylamine β - Methylphenethylamine Methamphetamine 3 - MMA Norfenfluramine Phentermine o - PIT Propylhexedrine RO5166017 N, N - Dimethylphenethylamine Neutral antagonists Inverse agonists EPPTB ( RO5212773 ) TAAR2 Agonists 3 - Iodothyronamine Phenethylamine Tyramine Neutral antagonists TAAR5 Agonists Dimethylethylamine Trimethylamine Neutral antagonists Inverse agonists 3 - Iodothyronamine References for all endogenous human TAAR1 ligands are provided at List of trace amines References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see TAAR for references. See also : Receptor / signaling modulators Phenethylamines Phenethylamines Psychedelics : 25B - NBOMe 25C - NBOMe 25D - NBOMe 25I - NBOMe 25N - NBOMe 2C - B 2C - B - AN 2C - Bn 2C - Bu 2C - C 2C - CN 2C - CP 2C - D 2C - E 2C - EF 2C - F 2C - G 2C - G - 1 2C - G - 2 2C - G - 3 2C - G - 4 2C - G - 5 2C - G - 6 2C - G-N 2C - H 2C - I 2C - iP 2C - N 2C - NH2 2C - O 2C - O - 4 2C - P 2C - Ph 2C - SE 2C - T 2C - T - 2 2C - T - 3 2C - T - 4 2C - T - 5 2C - T - 6 2C - T - 7 2C - T - 8 2C - T - 9 2C - T - 10 2C - T - 11 2C - T - 12 2C - T - 13 2C - T - 14 2C - T - 15 2C - T - 16 2C - T - 17 2C - T - 18 2C - T - 19 2C - T - 20 2C - T - 21 2C - T - 22 2C - T - 22.5 2C - T - 23 2C - T - 24 2C - T - 25 2C - T - 27 2C - T - 28 2C - T - 30 2C - T - 31 2C - T - 32 2C - T - 33 2C - TFE 2C - TFM 2C - YN 2C - V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi - 2C - T - 4 TCB - 2 Stimulants : Phenylethanolamine Hordenine Phenethylamine α - Methylphenethylamine ( amphetamine ) β - Methylphenethylamine m - Methylphenethylamine N - Methylphenethylamine o - Methylphenethylamine p - Methylphenethylamine Entactogens : Lophophine MDPEA MDMPEA Others : BOH DMPEA Amphetamines Psychedelics : 3C - BZ 3C - E 3C - P Aleph Beatrice Bromo - DragonFLY D - Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA - 2 Psi - DOM TMA TeMA Stimulants : 2 - FA 2 - FMA 3 - FA 3 - FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine ( Dextroamphetamine, Levoamphetamine ) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine ( Dexfenfluramine, Levofenfluramine ) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4 - Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine ( Dextromethamphetamine, Levomethamphetamine ) Methoxyphenamine MMA Morforex Norfenfluramine L - Norpseudoephedrine N, alpha - Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens : 4 - FA 4 - FMA 4 - MA 4 - MMA 4 - MTA 5 - APB 5 - APDB 5 - EAPB 5 - IT 5 - MAPB 5 - MAPDB 6 - APB 6 - APDB 6 - Chloro - MDMA 6 - EAPB 6 - IT 6 - MAPB 6 - MAPDB EDA IAP 2, 3 - MDA 3, 4 - MDA ( tenamfetamine ) MDEA MDHMA MDMA ( midomafetamine ) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others : 3, 4 - DCA Amiflamine DiFMDA Selegiline ( also D - Deprenyl ) Phentermines Stimulants : Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens : MDPH MDMPH Others : Cericlamine Cathinones Stimulants : 3 - FMC 4 - MC 4 - BMC 4 - CMC 4 - EMC 4 - FMC 4 - MEC 4 - MeMABP 4 - MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB Pentedrone Pentylone Radafaxine Entactogens : 3, 4 - DMMC 3 - MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone Phenylisobutylamines Entactogens : 4 - CAB 4 - MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants : Phenylisobutylamine Phenylalkylpyrrolidines Stimulants : α - PBP α - PHP α - PPP α - PVP MDPBP MDPPP MDPV 4 - MePBP 4 - MePHP 4 - MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone Catecholamines ( and close relatives ) 6 - FNE 6 - OHDA a-Me - DA a-Me - TRA Adrenochrome Ciladopa D - DOPA ( Dextrodopa ) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L - DOPA ( Levodopa ) L - DOPS ( Droxidopa ) L - Phenylalanine L - Tyrosine m - Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N, N - Dimethyldopamine Nordefrin ( Levonordefrin ) Norepinephrine Norfenefrine ( m - Octopamine ) Normetanephrine Orciprenaline p - Octopamine p - Tyramine Phenylephrine Synephrine Miscellaneous AL - LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH - LAD Famprofazone Fluorolintane Hexapradol IP - LAD Lysergic acid amide Lysergic acid 2 - butyl amide Lysergic acid 2, 4 - dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT - 45 PARGY - LAD Phenibut PRO-LAD Pronethalol Salbutamol ( Levosalbutamol ) Solriamfetol Theodrenaline Thiamphenicol UWA - 101 Drugs from PiHKAL AEM AL Aleph Aleph - 2 Aleph - 4 Aleph - 6 Aleph - 7 Ariadne Asymbescaline Buscaline Beatrice Bis - TOM BOB BOD BOH BOHD BOM 4 - Bromo - 3, 5 - dimethoxyamphetamine 2 - Bromo - 4, 5 - methylenedioxyamphetamine 2C - B 3C - BZ 2C - C 2C - D 2C - E 3C - E 2C - F 2C - G 2C - G - 3 2C - G - 4 2C - G - 5 2C - G-N 2C - H 2C - I 2C - N 2C - O 2C - O - 4 2C - P CPM 2C - SE 2C - T 2C - T - 2 2C - T - 4 psi - 2C - T - 4 2C - T - 7 2C - T - 8 2C - T - 9 2C - T - 13 2C - T - 15 2C - T - 16 2C - T - 17 2C - T - 19 2C - T - 21 4 - D beta - D DESOXY 2, 4 - DMA 2, 5 - DMA 3, 4 - DMA DMCPA DME DMMDA DMMDA - 2 DMPEA DOAM DOB DOBU DOC DOEF DOET DOI DOM psi - DOM DON DOPR Escaline EEE EEM EME EMM Ethyl - J ( EBDB ) Ethyl - K F - 2 F - 22 Flea G - 3 G - 4 G - 5 G-N Ganesha HOT - 2 HOT - 7 HOT - 17 IDNNA Isomescaline Isoproscaline Iris J ( BDB ) Lophophine PMA Mescaline Madam - 6 Methallylescaline MDA MDAL MDBU MDBZ MDCPM MDDM MDE MDHOET MDIP MDMA MDMC ( EDMA ) MDMEO MDMEOET MDMP MDOH MDPEA MDPH MDPL MDPR Metaescaline MEDA MEE MEM MEPEA Meta - DOB Meta - DOT Methyl - DMA Methyl - DOB Methyl - J ( MBDB ) Methyl - K Methyl - MA ( PMMA ) Methyl - MMDA - 2 MMDA MMDA - 2 MMDA - 3a MMDA - 3b MME Metaproscaline MPM Ortho - DOT Proscaline Phenescaline Phenethylamine Propynyl Symbescaline 2, 3, 4, 5 - Tetramethoxyamphetamine 3 - TASB 4 - TASB 5 - TASB Thiobuscaline 3 - TE 4 - TE 3 - TIM 4 - TIM 5 - TIM 3 - TM 4 - TM TMA TMA - 2 TMA - 3 TMA - 4 TMA - 5 TMA - 6 3 - TME 4 - TME 5 - TME 2T - MMDA - 3a 4T - MMDA - 2 2 - TOET 5 - TOET 2 - TOM 5 - TOM TOMSO Thioproscaline Trisescaline 3 - TSB 4 - TSB 3 - T - Trisescaline 4 - T - Trisescaline Retrieved from `` https://en.wikipedia.org/w/index.php?title=MDMA&oldid=807119712 '' Categories : Drugs not assigned an ATC code 5 - HT1A agonists 5 - HT2A agonists 5 - HT2B agonists 5 - HT2C agonists Substituted amphetamines Benzodioxoles Entactogens and empathogens Entheogens Euphoriants German inventions Methamphetamines Serotonin - norepinephrine - dopamine releasing agents Serotonin receptor agonists Stimulants TAAR1 agonists VMAT inhibitors Hidden categories : CS1 maint : Extra text : editors list CS1 maint : Uses authors parameter CS1 maint : Uses editors parameter CS1 maint : Extra text : authors list CS1 maint : Multiple names : authors list Pages using web citations with no URL Pages with DOIs inactive since 2017 CS1 Polish - language sources ( pl ) Webarchive template wayback links Wikipedia pages semi-protected against vandalism Use dmy dates from August 2017 Infobox drug articles with non-default infobox title Drugboxes which contain changes to watched fields Articles containing potentially dated statements from 2017 All articles containing potentially dated statements Articles containing potentially dated statements from 2015 Wikipedia articles needing page number citations from September 2015 All pages needing factual verification Wikipedia articles needing factual verification from October 2014 All articles with unsourced statements Articles with unsourced statements from January 2015 Articles with unsourced statements from April 2015 Articles with unsourced statements from August 2015 All articles with vague or ambiguous time Vague or ambiguous time from January 2015 Articles containing potentially dated statements from October 2015 Articles containing video clips Talk View source Contents About Wikipedia Български Boarisch Català Čeština Cymraeg Dansk Deutsch Eesti Español Esperanto Euskara فارسی Føroyskt Français Gaeilge Galego 한국어 Hrvatski Bahasa Indonesia Íslenska Italiano עברית Latina Latviešu Lietuvių Limburgs Magyar Bahasa Melayu Nederlands 日本 語 Norsk Norsk nynorsk ଓଡ଼ିଆ Polski Português Română Русский Scots Simple English Slovenčina Slovenščina Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska Türkçe Українська Tiếng Việt 粵語 中文 Edit links This page was last edited on 26 October 2017, at 01 : 10. 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Question: where did the name molly come from for the drug
Answer: short for 'molecule'