 | |
 | |
| 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 |
|
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| ChemSpider |
|
| UNII | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C12H16N2 |
| Molar mass | 188.274 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
4-Methyl-α-methyltryptamine (4-Me-αMT or4-Me-AMT), also known as4,α-dimethyltryptamine (4,α-DMT) and by its developmental code nameMP-809, is anexperimentalantidepressant of thetryptamine andα-alkyltryptamine families.[3][4][5][1][6][7] It is closelystructurally related toserotonergic psychedelics andentactogens likeα-methyltryptamine (αMT) andα-ethyltryptamine (αET).[1] 4-Me-αMT was investigated as an antidepressant bySandoz inCanada in the early 1960s, although it was never marketed.[3][1][6][7]
It is active at adosage of 20 to 60 mgorally in humans, though described as being an antidepressant rather than ahallucinogen.[1][2] It was found to be effective as an antidepressant in preliminaryclinical studies.[3][6]Alexander Shulgin has said that 4-Me-αMT produced somefeelings of unreality at a dose of 20 mg, as well asskin flushing,muscle tightness, andmydriasis.[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]
4-Me-αMT partially reversesreserpine-inducedbehavioral depression in rodents (by up to 60%), but does not producehyperlocomotion.[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- andpsychostimulant-likepotency compared to αMT.[10] It is also less active than αET.[10] The drug is said to have very weakmonoamine oxidase inhibition.[3][6]
4-Me-αMT was first described in thescientific literature by 1962.[6]
Three related compounds deserve specific mention. The 4-methyl homologue of α-MT, α,4-dimethyltryptamine (α,4-DMT), is orally active in humans at 20mg and produces some feelings of unreality, with neurological toxicity including skin flushing and eye dilation. The 4-hydroxy analogue (4-HO-α-MT) has been observed by some to evoke visual changes, accompanied by dizziness and mild depression. In the 15—20mg range (orally) there is occasional tachycardia, headache, and diarrhea. And the complete relocation of the 3-(2-aminopropyl)-chain of α- MT to the 5-position creates an isomer called 5-IT which, with orally produces a state of increased heart rate, anorexia, diuresis and slight hyperthermia, all lasting about 12 hours. None of these materials could be called hallucinogens.
Methyl-2-methyltryptamine [4-methyl-α-methyltryptamine]: Methyl-2-methyltryptamine is one of the newer antidepressants which was tested by Sandoz in Canada. The 4-substituted indoles are interesting compounds and it is not surprising this compound was active. Its LD-50 for mice was 55 mg/kg given intravenously and 90 mg/kg given subcutaneously. The LD-50 for rabbits given intravenously was 6 mg/kg. It was less toxic than IT-290. The 4-methyl derivative was a weak monoamine oxidase inhibitor. In rats it abolished the reserpine effect but had less synergistic effect with 5-hydroxytryptophan and a-dopa than did Catron. Preliminary clinical investigations showed it was an antidepressant and was beneficial in two thirds of a small group of neurotic patients.
A single mention has been made of the antidepressant utility of a ring-substituted homolog, 4α-dimethyltryptamine (XXV), but no details are presented (Hoffer and Osmond, 1967b). [...] Hoffer, A., and Osmond, H. (1967b). "The Hallucinogens," p. 468. Academic Press, New York.
A number of isomers and homologs of these alkylated tryptamines have been evaluated in clinical studies. The homologation of the α-methyl group of 60.29j to an ethyl radical results in a drug that has been employed experimentally as an antidepressant under the trade name of Monase (60.30, 129). It is considerably less potent than 60.29j, with dosages of 150 mg needed to produce a talkative intoxication. The addition of a methyl group at the 4 position yields α,4-dimethyltryptamine,60.31, which has also been reported to have antidepressant properties, but there are no experimental details given (131). [...] 131. A. Hoffer and H. Osmond. The Hallucinogens, Academic. New York. 1967. p. 468.
The analogue with the methyl group relocated to the indolic 4-position (4,α-DMT) has been looked at in man. At an oral dose of 20 milligrams, there are reports of feelings of unreality. External body signs include flushing, muscle tightness, and eye dilation.
