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| Other names | 1-Methoxy-DMT; 1-MeO-DMT; 1-Methoxydimethyltryptamine; 1-Methoxy-N,N-dimethyltryptamine |
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| Formula | C13H18N2O |
| Molar mass | 218.300 g·mol−1 |
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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 in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved) that it might bepsychoactive.[3] No reports on lespedamine'sbiological activity are known to have been published.[3] Lespedamine is not an explicitlycontrolled substance in theUnited States, but may be considered aSchedule I controlled substance in this country as it is apositional isomer of5-MeO-DMT.[4][5]
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? [...]
