Α,N,O-TMS

α,N,O-TMS
Clinical data
Other namesα,N,O-Trimethylserotonin; α,N,O-TMS; 5-Methoxy-α,N-dimethyltryptamine; 5-MeO-α,N-DMT; 5-MeO-α-Me-NMT
Routes of
administration		Oral[1]
ATC code
  • None
Identifiers
IUPAC name
  • [1-(5-methoxy-1H-indol-3-yl)propan-2-yl](methyl)amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
SMILES
  • O(c1cc2c(cc1)[nH]cc2CC(NC)C)C
InChI
  • InChI=1S/C13H18N2O/c1-9(14-2)6-10-8-15-13-5-4-11(16-3)7-12(10)13/h4-5,7-9,14-15H,6H2,1-3H3 checkY
  • Key:IYEMYZOLBLHKFE-UHFFFAOYSA-N checkY
  (verify)

α,N,O-Trimethylserotonin (α,N,O-TMS), also known as 5-methoxy-α,N-dimethyltryptamine (5-MeO-α,N-DMT), is a psychedelic drug of the tryptamine and substituted α-alkyltryptamine families.[1] Its abbreviated nomenclature is derived from its structure, as it is α,N,O-trimethyl serotonin.[1] The drug is taken orally.[1]

α,N,O-TMS was first synthesized by Alexander Shulgin.[1]

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Shulgin lists the dose as 10 to 20 mg orally and the duration as 6 to 8 hours.[1] The drug is significantly less potent than its non-N-methylated parent compound 5-MeO-AMT (5-methoxy-α-methyltryptamine), which has a dose range of 2.5 to 4.5 mg and a duration of 12 to 18 hours.[1]

Interactions

Chemistry

Analogues

A derivative of α,N,O-TMS, α,N,N,O-tetramethylserotonin (α,N,N,O-TeMS), also known as 5-methoxy-α-methyl-N,N-dimethyltryptamine (5-MeO-α-Me-DMT), has also been described.[1][2] However, it has not been synthesized or described and its dose, duration, and effects are unknown.[1]

See also

References

  1. 1 2 3 4 5 6 7 8 9 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. pp. 408, 425. ISBN 0-9630096-9-9. OCLC 38503252.
  2. ↑ "5-MeO-α-methyl-DMT". Isomer Design. 11 November 2024. Retrieved 26 November 2024.
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