Alpha-methyltryptamine

α-Methyltryptamine

Clinical data
Routes of administration	Oral, Insufflation, Rectal, Smoked, IM, IV
ATC code	none
Legal status
Legal status	AU: S8 (Controlled) CA: Unscheduled DE: Anlage I (Controlled) UK: Class A US: Schedule I
Identifiers
IUPAC name 1-(1H-Indol-3-yl)propan-2-amine
Synonyms	Indopan; IT-290, IT-403, U-14,164E, 3-IT
CAS Number	299-26-3 Y
PubChem CID	9287
DrugBank	DB01446 Y
ChemSpider	8930 Y
ChEBI	CHEBI:59020 Y
ChEMBL	CHEMBL30713 Y
ECHA InfoCard	100.005.522
Chemical and physical data
Formula	C11H14N2
Molar mass	174.24 g/mol
3D model (Jmol)	Interactive image
SMILES NC(CC1=CNC2=C1C=CC=C2)C
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

α-Methyltryptamine (abbreviated as αMT, AMT) 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, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

αMT is tryptamine with a methyl substituent at the alpha carbon. This alpha substitution makes it a relatively poor substrate for Monoamine_oxidase_A, thereby prolonging αMT's half-life, allowing it to reach the brain and enter the central nervous system. 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.

αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine, and as a non-selective serotonin receptor agonist.