Compound: MDMA
SMILES: O1c2c(ccc(c2)CC(NC)C)OC1
InChIKey: SHXWCVYOXRDMCX-UHFFFAOYSA-N
Synonyms: MDMA, Ecstasy, 3,4-methylenedioxymethamphetamine, Midomafetamine, 42542-10-9, Methylenedioxymethamphetamine, DL-(3,4-Methylenedioxy)methamphetamine, N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE, (RS)-3,4-(methylenedioxy)methamphetamine, N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine, 1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine, midomafetamina, KE1SEN21RM, Methylenedioxymetamphetamine, Methylenedioxymethamfetamine, (+-)-(3,4-Methylenedioxy)methamphetamine, CHEBI:1391, 1,3-Benzodioxole-5-ethanamine, N,alpha-dimethyl-, 3,4-methylenedioxymetamphetamine, Mandy [Street Name], Molly [Street Name], XTC [Street Name], Phenethylamine, N,alpha-dimethyl-3,4-methylenedioxy-, 3,4-Methylenedioxy-N,alpha-dimethyl-beta-phenylethylamine, (+-)-N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane, Mandy (Street Name), Molly (Street Name), XTC (Street Name), [1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine, Ecstasy (Drug), midomafetaminum, (1-(2H-1,3-benzodioxol-5-yl)propan-2-yl)(methyl)amine, RefChem:6368, N Methyl 3,4 methylenedioxyamphetamine, N Methyl 3,4 methylenedioxyamphetamine Hydrochloride, Hydrochloride, N-Methyl-3,4-methylenedioxyamphetamine, 980-806-5, Molly, HSDB 6929, MANDY, DEA No. 7405, Midomafetamine [USAN], (+-)-N-Methyl-3,4-(methylenedioxy)amphetamine, CHEMBL43048, XTC, 1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine, 1,3-Benzodioxole-5-ethanamine, N,.alpha.-dimethyl-, NCGC00168266-02, UNII-KE1SEN21RM, CCRIS 9277, (+)-3,4-methylenedioxymethamphetamine, MDMA (Ecstasy), rac-3,4-Methylenedioxymethamphetamine-D5, (+/-)-(3,4-Methylenedioxy)methamphetamine, Midomafetamine [WHO-DD], Epitope ID:178091, MDMA [MI], Midomafetamine (USAN/INN), MIDOMAFETAMINE [INN], SCHEMBL44210, Methylenedioxy Methamphetamine, DivK1c_000962, 3,4-MDMA, GTPL4574, SCHEMBL29353930, KBio1_000962, DTXSID90860791, NINDS_000962, BDBM707600, LFA76543, RCA14289, BDBM50010588, PDSP1_001522, PDSP2_001506, 3,4-methylenedioxy-n-methylamphetamine, AKOS006283463, DB01454, IDI1_000962, NCGC00168266-01, METHYLENEDIOXYMETHAMFETAMINE [MART.], D,L-3,4-METHYLENEDIOXYMETHAMPHETAMINE, NS00010441, C07577, D11172, Q69488, (+/-)-3,4-METHYLENEDIOXYMETHAMPHETAMINE, (+/-)-N-Methyl-3,4-(methylenedioxy)amphetamine, N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE [HSDB], 1-(2H-1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine, PHENETHYLAMINE, N,.ALPHA.-DIMETHYL-3,4-METHYLENEDIOXY-, (RS)-1-(BENZO(D)(1,3)DIOXOL-5-YL)-N-METHYLPROPAN-2-AMINE, (+/-)-N,.ALPHA.-DIMETHYL-3,4-(METHYLENEDIOXY)PHENETHYLAMINE, (+/-)-N-METHYL-1-(3,4-METHYLENEDIOXYPHENYL)-2-AMINOPROPANE, rac-MDMA (rac-3,4-Methylenedioxymethamphetamine) 1.0 mg/ml in Methanol
Theoretical properties:
molecular_formula: C11H15NO2
molecular_weight: 193.24 g/mol
exact_mass: 193.110278721 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 14
topological_polar_surface_area: 30.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Oil
color: Oil
boiling_point: BP: 100-110 °C at 0.4 mmHg
Descriptions:
{"pubchem": "3,4-methylenedioxymethamphetamine is a member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5. It has a role as a neurotoxin. It is a member of amphetamines and a member of benzodioxoles.", "chebi": "A member of the class of  benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.", "chembl": "MIDOMAFETAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.", "wikipedia": "3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy in tablet form, and molly in crystal form, is an entactogen with stimulant and minor psychedelic properties. \nMDMA was first synthesized in 1912 by Merck chemist Anton K\u00f6llisch. It was used to enhance 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. Tablets sold as ecstasy may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine. In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population). In the United States, as of 2017, about 7% of people have used MDMA at some point in their lives and 0.9% have used it in the last year. The lethal risk from one dose of MDMA is estimated to be from 1 death in 20,000 instances to 1 death in 50,000 instances.\nThe purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours. Short-term adverse effects include grinding of the teeth, blurred vision, sweating, and a rapid heartbeat, and extended use can also lead to addiction, memory problems, paranoia, and difficulty sleeping. Deaths have been reported due to increased body temperature and dehydration. MDMA acts primarily by increasing the release of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain. It belongs to the substituted amphetamine classes of drugs. MDMA is structurally similar to mescaline (a psychedelic), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin, norepinephrine, and dopamine.\nMDMA has limited approved medical uses in a small number of countries, but is illegal in most jurisdictions. MDMA-assisted psychotherapy may substantially improve PTSD symptoms, response, and remission rates compared to psychotherapy alone, but the evidence is low to very low certainty and safety data are limited, with some increased transient adverse events. In the United States, the Food and Drug Administration (FDA) has given MDMA breakthrough therapy status (though there are no current clinical indications in the US). Canada has allowed limited distribution of MDMA upon application to and approval by Health Canada. In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.\n\n"}