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| Names | |
|---|---|
| Preferred IUPAC name 2-(1-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine | |
| Other names 1-Methoxy-DMT; 1-MeO-DMT; 1-Methoxydimethyltryptamine; 1-Methoxy-N,N-dimethyltryptamine | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| UNII | |
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| Properties | |
| C13H18N2O | |
| Molar mass | 218.300 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Lespedamine, also known as1-methoxy-N,N-dimethyltryptamine (1-methoxy-DMT or1-MeO-DMT), is anindole alkaloid andsubstituted tryptamine present in the plantLespedeza bicolor.[1][2] The alkaloid bears a close structural resemblance to thepsychedelic alkaloiddimethyltryptamine (DMT) and it was speculated byAlexander Shulgin inTiHKAL that it might bepsychoactive.[3] No reports on lespedamine'sbiological activity are known to have been published.[3]Hamilton Morris askedentheogenethnobotanistJonathan Ott about lespedamine and its possible activity during an interview, but Ott was unfamiliar with it.[4]
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? [...]
