4-Methyl-α-methyltryptamine

4-Methyl-α-methyltryptamine (4-Me-αMT or 4-Me-AMT), also known as 4,α-dimethyltryptamine (4,α-DMT) and by its developmental code name MP-809, is an experimental antidepressant of the tryptamine and α-alkyltryptamine families.^{[3][4][5][1][6][7]} It is closely structurally related to serotonergic psychedelics and entactogens like α-methyltryptamine (αMT) and α-ethyltryptamine (αET).^[1] 4-Me-αMT was investigated as an antidepressant by Sandoz in Canada in the early 1960s, although it was never marketed.^[3][1][6][7]

4-Methyl-α-methyltryptamine

Clinical data
Other names	4-Me-αMT; 4-Me-AMT; 4-Methyl-αMT; 4-Methyl-AMT; 4,α-Dimethyltryptamine; 4,α-DMT; MP-809; MP809; Methyl-2-methyltryptamine
Routes of administration	Oral[1][2]
Drug class	Antidepressant
ATC code	None
Legal status
Legal status	Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Identifiers
IUPAC name 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine
CAS Number	3569-29-7 Y
PubChem CID	28806639
ChemSpider	25392939 Y
UNII	QY99ES7YWD
CompTox Dashboard (EPA)	DTXSID70708203
Chemical and physical data
Formula	C12H16N2
Molar mass	188.274 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(N)Cc2c1c([nH]c2)cccc1C
InChI InChI=1S/C12H16N2/c1-8-4-3-5-11-12(8)10(7-14-11)6-9(2)13/h3-5,7,9,14H,6,13H2,1-2H3 Y Key:KEOYEGHPRBDSKD-UHFFFAOYSA-N Y
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Dosage and effects

It is active at a dosage of 20 to 60 mg orally in humans, though described as being an antidepressant rather than a hallucinogen.^[1][2] It was found to be effective as an antidepressant in preliminary clinical studies.^[3][6] Alexander Shulgin has said that 4-Me-αMT produced some feelings of unreality at a dose of 20 mg, as well as skin flushing, muscle tightness, and mydriasis.^[2][8] However, he has said that it could not be called a hallucinogen at assessed doses^[2] and has listed the hallucinogenic dosage as being greater than 60 mg.^[9]

Pharmacology

4-Me-αMT partially reverses reserpine-induced behavioral depression in rodents (by up to 60%), but does not produce hyperlocomotion.^[6][10] This was the case at a dose of 50 mg/kg, whereas αMT produced clear hyperlocomotion and near-fully reversed reserpine-induced hypoactivity (by 95%) at a dose of 15 mg/kg.^[10] Hence, 4-Me-αMT shows reduced antidepressant- and psychostimulant-like potency compared to αMT.^[10] It is also less active than αET.^[10] The drug is said to have very weak monoamine oxidase inhibition.^[3][6]

History

4-Me-αMT was first described in the scientific literature by 1962.^[6]

See also

• 4-Methyl-αET
• 4-HO-αMT
• RS134-49