Α-Methyltryptamine

α-Methyltryptamine
Clinical data
Trade names	Indopan; Indopane
Other names	alpha-Methyltryptamine; αMT; α-ET; AMT; IT-290; IT-403 ((+)-αMT); NSC-97069; PAL-17; Ro 3-0926; U-14,164E; U-14,164-E; 3-(2-Aminopropyl)indole; 3-API; 3-IT; α-Methyl-3-indoleethanamine; Metryptamine; Amtryptamine
Routes of; administration	Oral, insufflation, rectal, smoked, IM, IV
Drug class	Entactogen; Stimulant; Psychedelic; Hallucinogen; Monoamine releasing agent; Serotonin receptor agonist; Monoamine oxidase inhibitor
ATC code	None;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class F2 (Prohibited psychotropics); CA: Unscheduled; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I;
Pharmacokinetic data
Onset of action	3–4 hours
Duration of action	12–24 hours
Identifiers
	IUPAC name 1-(1H-Indol-3-yl)propan-2-amine;
CAS Number	299-26-3 ;
PubChem CID	9287;
DrugBank	DB01446 ;
ChemSpider	8930 ;
UNII	BIK35ACJ0Q;
KEGG	C20127;
ChEBI	CHEBI:59020 ;
ChEMBL	ChEMBL30713 ;
CompTox Dashboard (EPA)	DTXSID00861850 ;
ECHA InfoCard	100.005.522
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	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 ; Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N ;
	(verify)

α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine family. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.

Side effects of αMT include agitation, restlessness, confusion, lethargy, pupil dilation, jaw clenching, and rapid heart rate, among others. αMT acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a serotonin receptor agonist, and as a weak monoamine oxidase inhibitor. αMT is a substituted tryptamine and is closely related to α-ethyltryptamine (αET) and other α-alkylated tryptamines.

αMT appears to have first been described by at least 1929. It started being more studied in the late 1950s and was briefly used as an antidepressant in the Soviet Union in the 1960s. The drug started being used recreationally in the 1960s, with use increasing in the 1990s, and cases of death have been reported. αMT is a controlled substance in various countries, including the United States.