2,α-Dimethyltryptamine
Chemical compound
title: "2,α-Dimethyltryptamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["2-alkyltryptamines", "alpha-alkyltryptamines", "psychedelic-tryptamines", "tihkal"] description: "Chemical compound" topic_path: "general/2-alkyltryptamines" source: "https://en.wikipedia.org/wiki/2,α-Dimethyltryptamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Chemical compound ::
::data[format=table title="Infobox drug"]
| Field | Value |
|---|---|
| Watchedfields | changed |
| verifiedrevid | 443314047 |
| image | 2,a-DMT.svg |
| image_class | skin-invert-image |
| width | 200px |
| image2 | 2,alpha-DMT_3d_structure.png |
| image_class2 | bg-transparent |
| width2 | 200px |
| pregnancy_AU | |
| pregnancy_US | |
| routes_of_administration | Oral |
| ATC_prefix | None |
| legal_AU | |
| legal_CA | |
| legal_UK | |
| legal_US | |
| CAS_number_Ref | |
| CAS_number | 4966-28-3 |
| UNII_Ref | |
| UNII | QAH3JR2679 |
| DrugBank_Ref | |
| ChemSpiderID_Ref | |
| ChemSpiderID | 23511903 |
| synonyms | 2,α-DMT; 2-Methyl-α-methyltryptamine; 2-Methyl-AMT; 2-Methyl-αMT; 2-Me-AMT; 2-Me-αMT |
| IUPAC_name | 1-(2-methyl-1H-indol-3-yl)propan-2-amine |
| C | 12 |
| SMILES | Cc1c(c2ccccc2[nH]1)CC(C)N |
| StdInChI_Ref | |
| StdInChI | 1S/C12H16N2/c1-8(13)7-11-9(2)14-12-6-4-3-5-10(11)12/h3-6,8,14H,7,13H2,1-2H3 |
| StdInChIKey_Ref | |
| StdInChIKey | AXZQFXRPULJFQK-UHFFFAOYSA-N |
| :: |
| Watchedfields = changed | verifiedrevid = 443314047 | image = 2,a-DMT.svg | image_class = skin-invert-image | width = 200px | image2 = 2,alpha-DMT_3d_structure.png | image_class2 = bg-transparent | width2 = 200px
| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | routes_of_administration = Oral | ATC_prefix = None | ATC_suffix =
| legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status =
| bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = | excretion =
| CAS_number_Ref = | CAS_number = 4966-28-3 | UNII_Ref = | UNII = QAH3JR2679 | PubChem = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 23511903 | synonyms = 2,α-DMT; 2-Methyl-α-methyltryptamine; 2-Methyl-AMT; 2-Methyl-αMT; 2-Me-AMT; 2-Me-αMT
| IUPAC_name = 1-(2-methyl-1H-indol-3-yl)propan-2-amine | C=12 | H=16 | N=2 | SMILES = Cc1c(c2ccccc2[nH]1)CC(C)N | StdInChI_Ref = | StdInChI = 1S/C12H16N2/c1-8(13)7-11-9(2)14-12-6-4-3-5-10(11)12/h3-6,8,14H,7,13H2,1-2H3 | StdInChIKey_Ref = | StdInChIKey = AXZQFXRPULJFQK-UHFFFAOYSA-N
2,α-Dimethyltryptamine (2,α-DMT), also known as 2-methyl-α-methyltryptamine (2-Me-αMT or 2-Me-AMT), is a tryptamine and a lesser-known psychedelic drug. It is the 2,α-dimethyl analogue of DMT and the 2-methyl derivative of α-methyltryptamine (αMT or AMT).
Use and effects
Alexander Shulgin lists the dose as 300 to 500mg, and the duration as 7 to 10hours in his book TiHKAL (Tryptamines I Have Known and Loved). 2,α-DMT causes mydriasis and paresthesia. It also produces a calm, drunk-like feeling.
Chemistry
Synthesis
The chemical synthesis of 2,α-DMT has been described.
Analogues
Analogues of 2,α-DMT (2-methyl-AMT) include 2-methyltryptamine (2-MT or 2-Me-T), 2,N,N-TMT (2-methyl-DMT), 2-methyl-DET, and 5-MeO-2-TMT (2-methyl-5-MeO-DMT), among others.
History
The chemical synthesis of 2,α-DMT was first reported in 1965.
References
References
- {{CiteTiHKAL
- (1965). "Studies in the Indole Series. Part I. Indolylalkylamines". Journal of the Chemical Society.
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