Lespedamine

Lespedamine
Names
	IUPAC name 2-(1-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
Identifiers
CAS Number	4335-93-7;
3D model (JSmol)	Interactive image;
ChemSpider	9313707;
PubChem CID	11138594;
	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; InChI=1/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-UHFFFAOYAO;
	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] 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. PMID 11201232.

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[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. PMID 11201232.