Lespedamine is an indole alkaloid and substituted tryptamine present in the plant Lespedeza bicolor.[1][2] The alkaloid bears a close structural resemblance to the psychedelic alkaloid dimethyltryptamine and was speculated to have psychoactivity by Alexander Shulgin. No reports on lespedamine's biological activity have been published.

Lespedamine
Names
Preferred IUPAC name
2-(1-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • O(n2c1ccccc1c(c2)CCN(C)C)C
Properties
C13H18N2O
Molar mass 218.300 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

References

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  1. ^ Somei M, Yamada F, Kurauchi T, 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". Chem. Pharm. Bull. 49 (1): 87–96. doi:10.1248/cpb.49.87. hdl:2297/43978. PMID 11201232.
  2. ^ Morimoto, Hiroshi; Oshio, Haruji (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.