alpha-Methyltryptamine

α-Methyltryptamine

Systematic (IUPAC) name
2-(1H-indol-3-yl)-1-methyl-ethylamine
Clinical data
Pregnancy cat.	?
Legal status	Controlled (S8) (AU) ? (CA) ? (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	eMolecules & PubChem
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.

History

In the 1990s αMT resurfaced as a drug of recreational use via easy access through the internet, leading to its placement along with 5-MeO-DiPT as schedule I controlled substances in the Controlled Substances Act of the United States on April 4, 2003. αMT is still legal in most of the world.

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 also 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.^{[citation needed]}

Like many other serotonin releasing agents, αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity at very high doses, and the same likely holds true for αMT as well, though no studies have been performed to verify this as of yet. However, based on anecdotal reports, both αMT and αET appear to produce considerably less of a hangover in comparison to MDMA, although this is not necessarily an indication of long-term safety.

Despite some experiential similarities, αMT is fairly different chemically from MDMA, and is part of the tryptamine family. It can cause strong distortions, delusions and hallucinations, and many other effects similar to those of LSD, psilocin and MDMA.

Dosage and effects

αMT was used as an antidepressant at doses of 5–10 mg. At these levels it improves mood and produces stimulation. With 20–30 mg, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours. 40+ mg is generally considered a strong dose, and may in rare cases or extreme doses last for 24 hours or more. αMT in freebase form can be smoked, and 2–5 mg is typically used.

Side effects

αMT can produce side effects including anxiety, restlessness, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, among others.

Legality

αMT is a schedule I controlled substance in the United States. 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.

αMT is reported to be a schedule 8 controlled drug in Australia, though this is unconfirmed. It is known that 5-MeO-αMT is schedule 9 in Australia however.

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