# 5-MeO-AMT

5-MeO-αMT, or 5-methoxy-α-methyltryptamine, also known as α,O-dimethylserotonin (Alpha-O), is a serotonergic psychedelic of the tryptamine family. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.

## Recreational use

5-MeO-AMT is supposedly sold in 4 mg tablets by the street name Alpha-O and taken as a recreational drug. Since the DEA arrests of the makers of a huge percentage of the United States' LSD in 2000, 5-MeO-AMT may have occasionally been sold under the guise of LSD in liquid, sugar cube, or blotter form, though this may be due to DEA reports of finding it on sugar cubes and blotters like LSD.
The most common route of administration for 5-MeO-AMT is orally. Anecdotal reports, however, have described snorting or smoking the substance. Intravenous (IV) and intramuscular (IM) routes are rarely, if ever, used outside research settings due to the high potency, powerful effects and quicker onset.

## Effects

The effects of 5-MeO-AMT occur at 4–7 mg orally for most users.
Erowid lists the following effects:

### Positive

* Increased energy
* Improved mood heading into euphoria at higher doses
* Increased sociability, gregariousness
* Increased giggling and laughter
* Increased sense of creative thinking
* Increased pleasure from sense of touch
* Intensification of sex for some users

### Neutral

* Lightheadedness
* Brightening of colors
* Visuals including motion, waves, breathing walls, etc. (usually at higher doses, over 4–5 mg)
* Increased attention to detail
* Auditory distortions and/or hallucinations (usually at higher doses)

### Negative

* Headache
* Body fatigue
* Chills from elevated body temperature (potential dehydration)
* Stress and extreme fatigue from long duration of effects.
* Nausea, diarrhea
* Vomiting
* Difficulty sleeping or resting for 12–24 hours after ingestion.
* Paranoia, irritability, anxiety (increasing with dose).
* Delusional, aggressive, or dissociated behaviour at very high doses (20+ mg)
* Risk of death

## Dangers

If misrepresented as LSD, 5-MeO-AMT can be extremely dangerous; users may take a number of "hits" of 5-MeO-AMT, assuming that it is LSD. Unlike LSD, which is very safe in overdose, 5-MeO-AMT can be very harmful or fatal. Particularly sensitive individuals can experience symptoms of overdose at dosages in the normal (for most users) range — as low as 20 mg. This has led to at least a few hospitalizations and possibly more than one death. It is likely that the overdose potential of the compound is due to its sympathomimetic effects, as the side effects noted in overdose cases include cardiac arrhythmia and seizure. It also seems that oral consumption is safer than insufflation.
Gloria Discerni, 18, died after overdosing on a drug initially believed to be LSD. Authorities learned months later that the drug wasn't LSD but a "designer drug" identified as 5-MeO-AMT.

## Pharmacology
### Pharmacodynamics

5-MeO-AMT activities :
| Target | Affinity (K$_i$, nM) |
| 5-HT$_{1A}$ | 46–194 (K$_i$) 680 (EC$_{50}$Tooltip Half-maximal effective concentration) |
| 5-HT$_{1B}$ | 417 (rat) |
| 5-HT$_{2A}$ | 3.1–34 (K$_i$) 2–8.4 (EC$_{50}$) |
| 5-HT$_{2B}$ | 4 (EC$_{50}$) |
| 5-HT$_{2C}$ | 90 |
| α$_{1A}$ | >12,000 |
| α$_{2A}$ | 11,000 |
| D$_1$ | >25,000 |
| D$_2$ | >25,000 |
| D$_3$ | >25,000 |
| H$_1$ | >25,000 |
| TAAR$_1$ | 1,100 (K$_i$) (rat) 4,800 (K$_i$) (mouse) >10,000 (EC$_{50}$) (human) |
| SERTTooltip Serotonin transporter | 8,270–12,000 (K$_i$) 1,980–17,000 (IC$_{50}$Tooltip half-maximal inhibitory concentration) 460 (EC$_{50}$) |
| NETTooltip Norepinephrine transporter | >22,000 (K$_i$) 37,000–78,000 (IC$_{50}$) 8,900 (EC$_{50}$) |
| DATTooltip Dopamine transporter | >26,000 (K$_i$) 2,690–43,000 (IC$_{50}$) 1,500 (EC$_{50}$) |
| MAO-ATooltip Monoamine oxidase A | 31,000 (IC$_{50}$) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: ||
5-MeO-AMT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT$_{1A}$, 5-HT$_{2A}$, and 5-HT$_{2B}$ receptors, among others. Its EC$_{50}$Tooltip half-maximal effective concentration at the serotonin 5-HT$_{2A}$ receptor has been found to be 2 to 8.4 nM. In relation to this, it is an extremely potent agonist of the serotonin 5-HT$_{2A}$ receptor in vitro, showing the highest potency of any other tryptamine assessed in one study. Its potency in activating the serotonin 5-HT$_{2A}$ receptor was 38-fold higher than that of dimethyltryptamine (DMT) and 361-fold higher than that of psilocin in the same study. It is also a highly potent agonist of the serotonin 5-HT$_{2B}$ receptor, with an EC$_{50}$ of 4 nM.
Whereas tryptamine, serotonin (5-hydroxytryptamine), and αMT show potent activity as monoamine releasing agents, including of serotonin, norepinephrine, and/or dopamine, the monoamine-releasing activity of 5-methoxylated tryptamine derivatives, like 5-methoxytryptamine, 5-MeO-NMT, and 5-MeO-DMT among others, is dramatically reduced or abolished. Accordingly, whereas the EC$_{50}$ values of αMT for induction of monoamine release are 22 to 68 nM for serotonin, 79 to 112 nM for norepinephrine, and 79 to 180 nM for dopamine, the EC$_{50}$ values in the case of 5-MeO-AMT are 460 nM for serotonin, 8,900 nM for norepinephrine, and 1,500 nM for dopamine. Similarly, it is of very low potency as a monoamine reuptake inhibitor (IC$_{50}$Tooltip half-maximal inhibitory concentration values >1,000 nM). Considering the very high potency of 5-MeO-AMT in activating the serotonin 5-HT$_{2A}$ receptor, its weak activities as a monoamine releasing agent and reuptake inhibitor are of questionable significance.
5-MeO-AMT is a weak monoamine oxidase A (MAO-A) inhibitor, with an IC$_{50}$ of 31,000 nM. For comparison, the IC$_{50}$ of AMT for MAO-A inhibition was 380 nM (~82-fold more potent than 5-MeO-AMT) and the IC$_{50}$ values of amphetamine (and its enantiomers) for MAO-A inhibition have been reported to be 11,000 to 70,000 nM.
5-MeO-AMT produces the head-twitch response, a behavioral proxy of psychedelic effects, in animals, and this is reversed by the serotonin 5-HT$_{2A}$ receptor antagonist ketanserin. It substitutes for other psychedelics such as DOM and LSD in animal drug discrimination tests, but does not substitute for entactogens like MDMA or psychostimulants like dextromethamphetamine or cocaine. The drug does not produce locomotor hyperactivity, behavioral sensitization, conditioned place preference, or self-administration, further indicating a lack of psychostimulant-like effects as well as misuse potential. 5-MeO-AMT is known to produce sympathomimetic effects, but these effects likely depend on serotonin 5-HT$_{2A}$ receptor activation rather than on monoamine release or reuptake inhibition. Other serotonergic psychedelics are also well known to produce sympathomimetic effects.

## Chemistry

5-MeO-AMT, also known as 5-methoxy-α-methyltryptamine, is a substituted tryptamine derivative. It is a derivative of tryptamine (T), 5-methoxytryptamine (5-MeO-T or 5-MT), and α-methyltryptamine (AMT or αMT) and is an analogue of other tryptamines like α-methylserotonin (5-HO-AMT) and 5-MeO-DMT. Some derivatives of 5-MeO-AMT include α,N-dimethyl-5-methoxytryptamine (5-MeO-α-Me-NMT or α,N,O-TMS) and α,N,N-trimethyl-5-methoxytryptamine (5-MeO-α-Me-DMT or α,N,N,O-TMS). As noted by Alexander Shulgin, the α-methylated tryptamines can be looked at as the tryptamine homologues of the amphetamines (α-methylated phenethylamines).
5-MeO-AMT is soluble in ethanol.

## History

5-MeO-AMT was first described in the scientific literature by 1980. It was described by Alexander Shulgin and colleagues.

## Legal status
### Australia

5-MeO-AMT is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.

### Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 5-MeO-αMT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Oct 1, 2004, in their regulation SFS 2004:696 listed as 5-metoxi-alfametyltryptamin (5-MeO-AMT), making it illegal to sell or possess.

### United Kingdom

5-MeO-αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT. This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that 5-MeO-αMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.

### United States

5-MeO-AMT is unscheduled at the federal level in the United States. However, the DEA considers the chemical a controlled substance analogue. The agency's opinion on this matter may change at any time.

#### Florida

5-MeO-AMT is a Schedule I controlled substance in the state of Florida, making it illegal to buy, sell, or possess.