α,N,N-TMT was briefly mentioned byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved), but he did not mention having tested it and did not describe its effects,dose, orduration.[2] In 2025,Hamilton Morris described havingsynthesized andassayed α,N,N-TMT.[1] He reported that it was an active psychedelic takenorally but was much less potent than AMT.[1]
^abcdHamilton 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 ofN-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.
^abcAlexander 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.ISBN978-0-9630096-9-2.OCLC38503252.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.
^abcdKalir A, Szara S (May 1966). "Synthesis and pharmacological activity of alkylated tryptamines".Journal of Medicinal Chemistry.9 (3):341–344.doi:10.1021/jm00321a017.PMID5960901.
