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Lespedamine
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
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
C 13 H 18 N 2 O
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Lespedamine , also known as 1-methoxy-N ,N -dimethyltryptamine (1-methoxy-DMT or 1-MeO-DMT ), is an indole alkaloid and substituted tryptamine present in the plant Lespedeza bicolor [ 1] [ 2] psychedelic alkaloid dimethyltryptamine (DMT) and it was speculated by Alexander Shulgin in TiHKAL that it might be psychoactive .[ 3] biological activity are known to have been published.[ 3] Hamilton Morris asked entheogen ethnobotanist Jonathan Ott about lespedamine and its possible activity during an interview, but Ott was unfamiliar with it.[ 4]
^ 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 . ^ a b Shulgin A (1997). Tihkal: The Continuation #6. DMT . ISBN 978-0-9630096-9-2 . Retrieved 17 August 2024 . 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? [...] ^ Hamilton Morris (1 September 2021). "PODCAST 28: A talk with Jonathan Ott" . The Hamilton Morris Podcast . Retrieved 20 January 2025 .
Tryptamines
1-Methyl-T 1-Methylpsilocin 2-HO-NMT 2-Me-DET 2-Methyl-5-HT 2,N ,N -TMT 4,5-DHP-DMT 4-AcO-DALT 4-AcO-DET 4-AcO-DiPT 4-AcO-DPT 4-AcO-EPT 4-AcO-MALT 4-AcO-MET 4-AcO-MiPT 4-AcO-NMT 4-AcO-TMT 4-F-5-MeO-DMT 4-Fluoro-T 4-HO-5-MeO-DMT 4-HO-DALT 4-HO-DBT 4-HO-DET 4-HO-DiPT 4-HO-DPT 4-HO-DSBT 4-HO-EPT 4-HO-MALT 4-HO-MET 4-HO-McPT 4-HO-McPeT 4-HO-MiPT 4-HO-MPT 4-HO-MsBT 4-HO-NALT 4-HO-NMT 4-HO-PiPT 4-HO-pyr-T 4-HO-TMT 4-HT 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-MET 5-Fluoro-T 5-HO-DiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N ,N -TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT 5-MeO-pyr-T 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine) 5-MeO-T-NBOMe 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-MT-NB3OMe 5-NOT 5,6-MeO-MiPT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-DHT 5,7-DHT 6-Fluoro-DMT 6-Fluoro-T 6-MeO-DMT 6-MeO-T 6-Methyl-T 7-Chloro-T 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Aeruginascin (4-PO-TMT) AGH-107 AGH-192 AH-494 ALiPT Alpertine Baeocystin (4-PO-NMT) Benzotript (4-chlorobenzoyl-L -tryptophan) Bufotenidine (5-HTQ) Bufotenin (5-HO-DMT) Convolutindole A CP-132,484 DALT DBT Desformylflustrabromine DET DiPT DMT DPT E-6801 E-6837 EiPT EMDT EPT Ethocybin (4-PO-DET) FGIN-127 FGIN-143 FT-104 HIOC Idalopirdine Indolylethylfentanyl Indorenate Iprocin (4-HO-DiPT) Isamide Lespedamine MBT MET Milipertine Miprocin (4-HO-MiPT) MiPT MPT MS-245 MSBT N -Feruloylserotonin (moschamine)NBoc-DMT NET/NETP NiPT NMT Norbaeocystin (4-PO-T) NTBT O-4310 O -PivalylbufotenineOxypertine PiPT Psilacetin (O -acetylpsilocin; 4-AcO-DMT) Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Pyr-T RS134-49 Serotonin (5-HT) Solypertine ST-1936 Tryptamine (T) Tryptophan Yuremamine Z2876442907 N -Acetyltryptaminesα-Alkyltryptamines
2,α-DMT 4-HO-αMT 4-HO-MPMI (lucigenol) 4-Me-αET 4-Me-αMT 5-Chloro-αET 5-Chloro-αMT 5-Ethoxy-αMT 5-Fluoro-αET 5-Fluoro-αMT 5-iPrO-αMT 5-MeO-α,N ,N -TMT 5-MeO-αET 5-MeO-αMT 5-MeO-MPMI 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Methyl-αET α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT) α-Methyltryptophan (αMTP) α,N -DMT (N -methyl-αMT) α,N ,N -TMT α,N ,O -TMS αET (etryptamine) αMT AL-37350A (4,5-DHP-αMT) BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT BNC-210 BW-723C86 CP-135807 IPAP (α,N -DPT) MPMI Triptans Cyclized tryptamines
Bay R 1531 Ciclindole Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD )Flucindole Harmala alkaloidsβ-carbolines (e.g., 6-MeO-THH , 9-Me-BC , β-carboline (norharman) , harmaline , harmalol , harmane , harmine , pinoline , tetrahydroharmine , tryptoline )Iboga alkaloidsDM-506 (ibogaminalog) , ibogaine , ibogamine , noribogaine , tabernanthalog , tabernanthine )LY-266,097 Metralindole NDTDI PHA-57378 PNU-22394 PNU-181731 RU-28306 Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine ) Isotryptamines Related compounds
