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.
Masanori Somei, Fumio Yamada, Takashi Kurauchi, Yoshiyuki Nagahama, Masakazu Hasegawa, Koji Yamada, Sakiko Teranishi, Haruhiko Sato, Chikara Kaneko
Chemical and Pharmaceutical Bulletin 2001 DOI: 10.1248/cpb.49.87 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | 5-MeO-DMT Serotonin |
| Citations | 41 |
| Key points | Regioselective nucleophilic substitution reactions of 1-hydroxytryptamines enable novel and simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine, as well as 5-benzyloxytryptamine and 1-methoxy-2-oxindoles. |
Abstract
Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.
Citations in the library
Cited by 4
- Psychedelic-inspired drug discovery using an engineered biosensor. Cell April 28, 2021
- Occurrence of bufotenin in the Osteocephalus genus (Anura: Hylidae). Toxicon September 15, 2005
- Synthesis of a deuterium‐labelled standard of bufotenine (5‐HO‐DMT) Journal of Labelled Compounds and Radiopharmaceuticals October 1, 2007
- ChemInform Abstract: The Chemistry of Indoles. Part 103. 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. ChemInform July 31, 2001
Cites 2
- Syntheses of Serotonin, N-Methylserotonin, Bufotenine, and Melatonin, and the First Total Synthesis of N-(Indol-3-yl)methyl-N-methyl-5-methoxytryptamine from Tryptamine through a Common Intermediate, 1-Hydroxytryptamine Heterocycles 1997
- Simple syntheses of lespedamine and 5-bromo-n,n-dimethyltryptamine based on 1-hydroxyindole chemistry Heterocycles 1995