Lespedamine

Lespedamine
Names
	Preferred IUPAC name 2-(1-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine
Identifiers
CAS Number	4335-93-7;
3D model (JSmol)	Interactive image;
ChemSpider	9313707;
PubChem CID	11138594;
UNII	6W73QAN9CK ;
CompTox Dashboard (EPA)	DTXSID601031963 ;
	InChI 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;
	SMILES O(n2c1ccccc1c(c2)CCN(C)C)C;
Properties
Chemical formula	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). Infobox references

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.

References

^ 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.
^ 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.

[Somei-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.

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