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Alphamethyltryptamine

α-Methyltryptamine
AMT.svg
Clinical data
Routes of
administration
Oral, Insufflation, Rectal, Smoked, IM, IV
ATC code
  • none
Legal status
Legal status
Identifiers
Synonyms Indopan; IT-290, IT-403, U-14,164E, 3-IT
CAS Number
PubChem CID
DrugBank
ChemSpider
ChEBI
ChEMBL
ECHA InfoCard 100.005.522
Chemical and physical data
Formula C11H14N2
Molar mass 174.24 g/mol
3D model (Jmol)
  

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.


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