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Chemical compound
Pharmaceutical compound
5-MeO-2-TMT
Clinical data
Other names5-Methoxy-2,N,N-trimethyltryptamine; 5-MeO-2,N,N-TMT; 5-MeO-TMT; 2-Methyl-5-methoxy-N,N-dimethyltryptamine; 2-Me-5-MeO-DMT; Indapex; MMDT; 5-Methoxy-2-methyl-DMT
Routes of
administration		Oral[1][2]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Pharmacokinetic data
Duration of action5–10 hours[1][2]
Identifiers
  • 2-(5-methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
  • CC1=C(C2=C(N1)C=CC(=C2)OC)CCN(C)C
  • InChI=1S/C14H20N2O/c1-10-12(7-8-16(2)3)13-9-11(17-4)5-6-14(13)15-10/h5-6,9,15H,7-8H2,1-4H3 checkY
  • Key:ACEHBQPPDDGCGZ-UHFFFAOYSA-N checkY
  (verify)

5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT, 5-MeO-TMT), also known as 2-methyl-5-methoxy-N,N-dimethyltryptamine (2-Me-5-MeO-DMT), is a serotonin receptor modulator and psychedelic drug of the tryptamine and 2-alkyltryptamine families.[1][3][4][2][5] It is taken orally.[1][2]

5-MeO-2-TMT was first synthesized by Alexander Shulgin and reported in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1]

Use and effects

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According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 5-MeO-TMT has a dose range of 75 to 150 mg orally and a duration of 5 to 10 hours.[1] It produces effects including sexual stimulation, enhanced orgasm, relaxation, sedation, tingling, sleep disturbances, chills and cold sensations, time dilation, reduced heart rate, reduced respiratory rate, mild nausea, motor incoordination, visual waviness, mild to pronounced closed-eye visuals, emotional lability, crying, body temperature fluctuations, uncomfortableness, gastrointestinal disturbances, and abdominal pain.[1] It has been said that 5-MeO-TMT at a dose of 150 mg is definitely hallucinogenic and can be compared to a moderate 300 mg dose of mescaline.[1]

Interactions

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Pharmacology

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Pharmacodynamics

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5-MeO-2-TMT activities
TargetKi (nM)
5-HT1A200
5-HT1B>10,000
5-HT1D250
5-HT1E1,800
5-HT1FND
5-HT2A>10,000 (rat)
5-HT2BND
5-HT2C4,020 (rat)
5-HT3ND
5-HT4ND
5-HT5A10,450
5-HT660–80
5-HT7145
α1A–α2CND
β1–β3ND
D1–D5>10,000
H1>10,000
H2ND
H3, H4>10,000
M1–M5>10,000
I1ND
σ1, σ2ND
TAAR1Tooltip Trace amine-associated receptor 1ND
SERTTooltip Serotonin transporter>10,000
NETTooltip Norepinephrine transporter6,380
DATTooltip Dopamine transporter>10,000
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][3][5]

The affinities of 5-MeO-TMT for numerous targets have been reported.[3][5] 2-Methyltryptamines like 5-MeO-TMT show a loss of affinity for the serotonin 5-HT2A receptor but retained affinity for the serotonin 5-HT6 receptor.[4][5][3] It also retains significant affinity for the serotonin 5-HT1A, 5-HT1D, and 5-HT7 receptors.[3][5] In contrast to 5-MeO-DMT, 5-MeO-TMT is orally active, suggesting that the 2-methyl group blocks metabolism by monoamine oxidase (MAO).[1]

Chemistry

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Synthesis

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The chemical synthesis of 5-MeO-2-TMT has been described.[1]

Analogues

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Society and culture

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5-MeO-2-TMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.[7]

United States

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5-MeO-2-TMT is not an explicitly controlled substance in the United States.[8] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 10 Erowid Online Books : "TIHKAL" - #45 5-MEO-TMT
  2. 1 2 Shulgin AT (2003). . In Laing RR (ed.). . Forensic Drug Handbook Series. Elsevier Science. pp.137. .
  3. 1 2 3 4 5 Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2) e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.
  4. 1 2 Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. Compared to 5-MeO-DMT (6), compounds with 2-position substituents displayed conserved affinity at the 5-HT6 receptor but not at the 5-HT2AR.138 For example, the methyl- (17, r5- HT2AR Ki > 10,000 nM), ethyl- (18, r5-HT2AR Ki > 10,000 nM), and phenyl- (19, r5-HT2AR Ki > 470 nM) substitutions totally abolished binding affinity for the 5-HT2AR (Figure 5B).138 [...] (138) Glennon, R. A.; Lee, M.; Rangisetty, J. B.; Dukat, M.; Roth, B. L.; Savage, J. E.; McBride, A.; Rauser, L.; Hufeisen, S.; Lee, D. K. H. 2-Substituted Tryptamines: Agents with Selectivity for 5-HT6 Serotonin Receptors. J. Med. Chem. 2000, 43, 1011−1018.
  5. 1 2 3 4 5 Glennon RA, Lee M, Rangisetty JB, Dukat M, Roth BL, Savage JE, McBride A, Rauser L, Hufeisen S, Lee DK (March 2000). "2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors". J Med Chem. 43 (5): 1011–1018. doi:10.1021/jm990550b. PMID 10715164.
  6. ↑ "Kᵢ Database". PDSP. 26 March 2025. Retrieved 26 March 2025.
  7. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  8. ↑ 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
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