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
Masanori Somei, Fumio Yamada, Harunobu Morikawa
Heterocycles 1997 DOI: 10.3987/com-97-s33 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Serotonin |
| Citations | 21 |
| Key points | Reports synthetic routes to serotonin, N-methylserotonin, bufotenine, and melatonin, and the first total synthesis of N-(indol-3-yl)methyl-N-methyl-5-methoxytryptamine, all starting from tryptamine through acid-catalyzed nucleophilic substitution of 1-hydroxytryptamines. |
Abstract
Simple syntheses of serotonin (la), N-methylserotonin (lb), bufotenine (lc), and melatonin (2), and the first total synthesis of N-(indol-3-y1)methyl-N-methyl-5-methoxytryptamine (3) from tryptamine (4a) are reported through acid catalyzed nucleophilic substitution reaction of 1-hydroxytryptamines.Tryptamine alkaloids such as serotonin (la, Scheme l)? N-methylserotonin (lb)?bufotenine (lc) ?arb
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
- Synthesis of a deuterium‐labelled standard of bufotenine (5‐HO‐DMT) Journal of Labelled Compounds and Radiopharmaceuticals October 1, 2007