Lespedamine

Lespedamine
Clinical data
Other names1-Methoxy-DMT; 1-MeO-DMT; 1-Methoxydimethyltryptamine; 1-Methoxy-N,N-dimethyltryptamine
Identifiers
  • 2-(1-methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CN(C2=CC=CC=C21)OC
  • InChI=1S/C13H18N2O/c1-14(2)9-8-11-10-15(16-3)13-7-5-4-6-12(11)13/h4-7,10H,8-9H2,1-3H3
  • Key:DXTZTYQDNUHCAB-UHFFFAOYSA-N

Lespedamine, also known as 1-methoxy-N,N-dimethyltryptamine (1-methoxy-DMT or 1-MeO-DMT), is an indole alkaloid and substituted tryptamine present in the plant Lespedeza bicolor. The alkaloid bears a close structural resemblance to the psychedelic alkaloid dimethyltryptamine (DMT) and it was speculated by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved) that it might be psychoactive. No reports on lespedamine's biological activity are known to have been published. Lespedamine is not an explicitly controlled substance in the United States, but may be considered a Schedule I controlled substance in this country as it is a positional isomer of 5-MeO-DMT.

See also

References

  1. ↑ Somei M, Yamada F, Kurauchi T, Nagahama Y, Hasegawa M, Yamada K, et al. (January 2001). "The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry". Chemical & Pharmaceutical Bulletin. 49 (1): 87–96. doi:10.1248/cpb.49.87. hdl:2297/43978. PMID 11201232.
  2. ↑ Morimoto H, Oshio H (22 February 1965). "Über Alkaloide, V Inhaltsstoffe vonLespedeza bicolor var.japonica, I. über Lespedamin, ein neues Alkaloid". Justus Liebigs Annalen der Chemie. 682 (1): 212–218. doi:10.1002/jlac.19656820121.
  3. 1 2 Shulgin A (1997). Tihkal: The Continuation. Transform Press. #6. DMT. ISBN 978-0-9630096-9-2. Retrieved 17 August 2024. Several simple substitution derivatives of DMT are known. Those that are known to be psychedelic have their own recipes, of course, but the others will be summarized here. The 1-methyl homologue of DMT (1,N,N-trimethyltryptamine) can be prepared from DMT in KOH and DMSO, with CH3I. It forms a picrate salt which melts at 175–179 °C, and bioxalate, mp 174–176 °C. It is more toxic than DMT in rats, but has an identical serotonin binding capacity. The compound with a methoxy group substituent at the 1-position is called Lespedamine, 1-MeO-DMT. With an NO bond, this should be classified as a substituted hydroxylamine. I would love to know if anyone anywhere has ever tried smoking it. I suspect it might very well be active, but it is, to my knowledge, untried. I wonder why it deserves a trivial name, vis., Lespedamine? [...]
  4. ↑ 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
  5. ↑ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register. Vol. 72, no. 231. p. 67850.