Α,N,N-Trimethyltryptamine

Psychoactive drug From Wikipedia, the free encyclopedia

α,N,N-Trimethyltryptamine (α,N,N-TMT, α-TMT, or ATMT), also known as α-methyl-N,N-dimethyltryptamine (α-methyl-DMT or α-Me-DMT) or as Alpha-N, is a psychedelic drug of the tryptamine and α-alkyltryptamine families.^[2]^[3] It is similar in chemical structure to other psychedelic tryptamines such as N,N-dimethyltryptamine (DMT) and α-methyltryptamine (αMT).^[3] It is taken orally.^[1]

Other namesα,N,N-TMT; α-TMT; ATMT; α-Methyl-N,N-dimethyltryptamine; α-Methyl-DMT; α-Me-DMT; Alpha-N

Routes of
administrationOral^[1]

Drug classSerotonergic psychedelic; Hallucinogen

CAS Number

4761-32-4^Y

Quick facts Clinical data, Other names ...

α,N,N-Trimethyltryptamine
Clinical data


Other names	α,N,N-TMT; α-TMT; ATMT; α-Methyl-N,N-dimethyltryptamine; α-Methyl-DMT; α-Me-DMT; Alpha-N
Routes of administration	Oral^[1]
Drug class	Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine
CAS Number	4761-32-4^Y
PubChem CID	134080494
ChemSpider	59718639
UNII	8AV9QTP9HK
CompTox Dashboard (EPA)	DTXSID401336121
Chemical and physical data
Formula	C₁₃H₁₈N₂
Molar mass	202.301 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN(C)C(C)Cc2c[nH]c1ccccc12
InChI InChI=1S/C13H18N2/c1-10(15(2)3)8-11-9-14-13-7-5-4-6-12(11)13/h4-7,9-10,14H,8H2,1-3H3 Key:XQFCCTPWINMCQJ-UHFFFAOYSA-N
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Use and effects

α,N,N-TMT was briefly mentioned by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved), but he did not mention having tested it and did not describe its effects, dose, or duration.^[2] In 2025, Hamilton Morris described having synthesized and assayed α,N,N-TMT.^[1] He reported that it was an active psychedelic taken orally but was much less potent than AMT.^[1]

Interactions

Pharmacology

Pharmacodynamics

The drug has been tested in animals and compared with α-methyltryptamine (αMT).^[3] It was found to produce similar effects as αMT, such as hyperlocomotion and reversal of reserpine-induced behavioral depression, but with only around half the potency of αMT.^[3]

Chemistry

Analogues

Analogues of α,N,N-TMT (N,N-dimethyl-AMT) include α-methyltryptamine (AMT), α,N-DMT (N-methyl-AMT), α-methylserotonin (AMS; 5-HO-AMT), 5-MeO-AMT (α,O-DMS), α,N,O-TMS (N-methyl-5-MeO-AMT), and α,N,N,O-TeMS (N,N-dimethyl-5-MeO-AMT), among others.^[2]

History

α,N,N-TMT was encountered as a novel designer drug in Europe by 2015.^[4]

Society and culture

Legal status

Canada

α,N,N-TMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.^[5]

United States

α,N,N-TMT is not an explicitly controlled substance in the United States.^[6] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

[1]
Hamilton Morris (29 April 2025). "POD 126: The Return of Psychedelic Selenium with Dr. Josh Hartsel". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 1:33:53–1:35:50. [Hartsel:] Speaking of these tryptamines, I'd like to point your attention to something I found like an interesting hole in the research. Like, you know what α-methyltryptamine is right? [Morris:] Of course, yeah. [Hartsel:] Yeah, there's a drug company that was developing those compounds in Russia and I can't remember why they took them off the shelf but they were interesting to me because they have a psychedelic element but they're also like monoamine transporter active. So they have some you know amphetamine-like activity and that's where you're starting to get into like MDMA realm. But the hole that I pointed out was that nobody ever made the dimethyl analogues. It was the weirdest thing. I looked into this research, like 5-methoxy-α-methyl-DMT. Up until about a year ago, I kept looking I couldn't find one instance of it. It is in the literature now. [...] [Hartsel:] The α,N,N-Dimethyl[tryptamine]. [Morris:] Oh yeah, I've made it and tried it actually. [Hartsel:] Oh you did? [Morris:] Yeah, yeah. [Hartsel:] Oh, well what did it do? [Morris:] It is active, it's an active psychedelic. It's reduced potency. I never got it to a dose where it produced particularly interesting effects. I can look up the exact dose. I think it was like... the only thing I remember is that I felt like it was making me sneeze a lot. But it was very pleasant. Nothing bad happened. But the dose just wasn't high enough. I think I took maybe 40 mg. So it was much less potent than AMT orally. The other issue of course is that it could be a prodrug of N-methyl-AMT, which is active, or AMT itself maybe. Also like I made it via reductive amination of AMT and the α-methyl group interferes with reductive amination more than you'd think.
[2]
Alexander T. Shulgin; Ann Shulgin (1997). "#8. α,N-DMT; TRYPTAMINE, α,N-DIMETHYL; INDOLE, 3-[2-(METHYLAMINO)PROPYL]; α,N-DIMETHYLTRYPTAMINE; 3-[2-(METHYLAMINO)PROPYL]INDOLE; ALPHA-N". TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. pp. 423–427. ISBN 978-0-9630096-9-2. OCLC 38503252. The application of this structural modification to the tryptamine area, gives α,N,N-trimethyltryptamine (α,N,N-TMT). The tertiary amine in the phenethylamine, N,N-dimethylamphetamine, showed a loss in its stimulant nature. Here, the adding of that additional methyl group gives a tertiary amine that has the skeleton of DMT. This base has been reported as having been made by either of two different routes, both starting with indole. Reaction with propyleneoxide gave the 3-indolyl-2-propanol which was treated first with PBr3 followed by dimethylamine. Or, reaction with chloropropionyl chloride gave a 1,3-bis intermediate which was converted to the amino ketone 3-(2-dimethylaminopropionyl)indole with dimethylamine. This was reduced to the same product, α,N,N-TMT, with LAH. The bimaleate salt had a melting point of 139–140 °C.
[3]
Kalir A, Szara S (May 1966). "Synthesis and pharmacological activity of alkylated tryptamines". Journal of Medicinal Chemistry. 9 (3): 341–344. doi:10.1021/jm00321a017. PMID 5960901.
[4]
"2015 Annual Reports on the implementation of Council Decision 2005/387/JHA". Europol. 23 October 2018. Retrieved 22 March 2025.
[5]
"Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
[6]
Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026