Simple syntheses of lespedamine and 5-bromo-n,n-dimethyltryptamine based on 1-hydroxyindole chemistry
Masanori Somei, Kensuke Kobayashi, Keiko Tanii, Toshihiko Mochizuki, Yumiko Kawada, Yashikazu Fukui
Heterocycles 1995 DOI: 10.3987/com-94-s26 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | 5-MeO-DMT DMT |
| Citations | 18 |
| Key points | Proposes that N,N-dimethyl-1-hydroxytryptamine serves as a common biosynthetic intermediate linking lespedamine, 5-bromo-N,N-dimethyltryptamine, and bufotenine, and reports the first syntheses of various 1-hydroxyindoles. |
Abstract
Various types of 1-hydroxyindoles were prepared for the first time.Through methylation or acid catalyzed nucleophilic bromination of N,N-dimethyl-1 -hydroxytryptamine, simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine were achieved, respectively.~espedaminez (1 a, Scheme 1) was isolated from Lespedeza bicolorvar.japonica Nakai and -b r o m o -~, ~-d i m e t h ~l t r y ~t a m i n e ~(2 a) from marine sponge Smenospongia aure.Bufotenine (3a),4 1 a, and 2 a seem to have no relation to each other.However, if we assume the existence of N,N-dirnethyl-I-hydroxytryptamine (4 a). 1 a, 2 a, and 3 a might be expected to originate from 4 a as a common intermediate.Along this biosynthetic working hypothesis,5 we have now achieved the simple syntheses of 1 a and 2 a through 4a.We have succeeded for the first time in the syntheses6 of various 1-hydroxyindoles, Initially, N,N-dimethyltryptamine ( 6) was prepared from indole (5) according to either the known two step sequence7 (87% yield) of N,N-dimethylindole-3-glyoxylamide formation and treatment with LiAIH4 or direct dimethylation of tryptamine8 (70% yield).Reduction of 6 with triethylsilane9 i n CF3COOH afforded 2,3-dihydro-N,N-dimethyltryptamine (7 a) in 92% yield.Oxidation of 7 a with Na2W04.2H20 and 30% ~~0 ~5 3 6 in MeOH-Hz0 produced 55% y i e l d of N,N-dimethyl-1hydroxytryptamine (4a, mp 179.5-1 80.0°C) as stable crystals.Subsequent methylation of 4 a with diazomethane afforded lespedamine (1 a) in 53% yield.One pot preparation of 1 a from 7 a i n
Comparable studies
Other theoretical and historical papers on 5-MeO-DMT, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| When the Endogenous Hallucinogenic Trace AmineN,N-Dimethyltryptamine Meets the Sigma-1 Receptor | 2009 | Theoretical or philosophical paper | |
| Analytical chemistry of synthetic routes to psychoactive tryptamines : Part I. Characterisation of the Speeter and Anthony synthetic route to 5-methoxy-N,N-diisopropyltryptamine using ESI-MS-MS and ESI-TOF-MS | 2004 | Theoretical or philosophical paper | |
| Enlightening the "Spirit Molecule": Photomodulation of the 5-HT2A Receptor by a Light-Controllable N,N-Dimethyltryptamine Derivative. | 2022 | Theoretical or philosophical paper | |
| Conformational, spectroscopic and nonlinear optical properties of biologically active N,N-dimethyltryptamine molecule: a theoretical study. | 2014 | Theoretical or computational study | |
| 5-Methoxy-N,N-dimethyltryptamine: An Ego-Dissolving Endogenous Neurochemical Catalyst of Creativity | 2019 | Theoretical or philosophical paper |
Citations in the library
Cited by 2
- 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. Chemical and Pharmaceutical Bulletin 2001
- ChemInform Abstract: The Chemistry of Indoles. Part 71. Simple Syntheses of Lespedamine and 5‐Bromo‐N,N‐dimethyltryptamine Based on 1‐Hydroxyindole Chemistry. ChemInform July 11, 1995