alpha-Methyltryptamine

α-Methyltryptamine

Systematic (IUPAC) name
2-(1H-indol-3-yl)-1-methyl-ethylamine
Clinical data
Pregnancy cat.	?
Legal status	Controlled (S8) (AU) Uncontrolled (CA) Legal (UK) Schedule I (US)
Routes	Oral, Insufflation, Rectal, Smoked, IM, IV
Identifiers
CAS number	299-26-3 Y
ATC code	None
PubChem	CID 9287
DrugBank	DB01446
ChemSpider	8930 Y
ChEBI	CHEBI:59020 Y
ChEMBL	CHEMBL30713 Y
Synonyms	Indopan; IT-290, IT-403, U-14,164E, 3-IT
Chemical data
Formula	C11H14N2
Mol. mass	174.24 g/mol
SMILES NC(C)CC1=C[N]C2=C1C=CC=C2
InChI InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3 Y Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

α-Methyltryptamine (αMT, AMT, Indopan), is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s.

Chemistry

αMT is tryptamine with a methyl substituent at the alpha carbon. Its chemical relation to tryptamine is analogous to that of amphetamine to phenethylamine, amphetamine being α-methylphenethylamine. αMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action.

Pharmacology

αMT acts as relatively balanced releasing agent of serotonin, norepinephrine, and dopamine, and as a non-selective serotonin receptor agonist. It acts as a very weak, non-selective and reversible inhibitor of the enzyme monoamine oxidase (MAO), but this is unlikely to be very significant if at all with typical doses.

Dosage and effects

Like many other serotonin releasing agents, αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity at very high doses.

Reported side effects include anxiety, restlessness, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, among other effects that might commonly be attributed to LSD, psilocybin and MDMA, such as delusions and hallucinations.

With 20–30 milligrams, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours. A dose exceeding 40mg is generally considered as strong. In rare cases or extreme doses the duration of effects might exceed 24 hours. αMT in freebase form is reported by users to have been smoked, with doses of between and 2–5 milligrams being cited.

In spite of some reported experiential similarities to MDMA, the chemicals are structurally unrelated; αMT is a tryptamine while MDMA is a phenethylamine.

Legality

In the 1990s, αMT resurfaced as a drug of recreational use courtesy of easy access on the Internet, leading to its placement, along with 5-MeO-DiPT, as a schedule I substance in the Controlled Substances Act of the United States on April 4, 2003.

It is legal in the United Kingdom, however, and does not fall under the tryptamine clause as its substituent is not on the nitrogen position. See "2001 Misuse of Drugs Act: Schedule 1, Regulation 3" for more information. Similarly, Canada has no mention of this substance in the Controlled Drugs and Substances Act.

The 5-Methoxy cousin, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this.

See also

• 4-Methyl-αMT
• 5-Fluoro-αMT
• 5-API
• 5-MeO-αMT
• α-Ethyltryptamine
• α,N-DMT
• α,N,N-TMT
• α-Methyl-5-HT

External links

• TiHKAL entry
• αMT Entry in TiHKAL • info
• Erowid page on αMT
• Lycaeum page on αMT