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

M Somei; F Yamada; T Kurauchi; Y Nagahama; M Hasegawa; K Yamada; S Teranishi; H Sato; C Kaneko

doi:10.1248/cpb.49.87

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 (Tokyo). 2001 Jan;49(1):87-96. doi: 10.1248/cpb.49.87.

Authors

M Somei¹, F Yamada, T Kurauchi, Y Nagahama, M Hasegawa, K Yamada, S Teranishi, H Sato, C Kaneko

Affiliation

¹ Faculty of Pharmaceutical Sciences, Kanazawa University, Japan. somei@dbs.p.kanazawa-u.ac.jp

PMID: 11201232
DOI: 10.1248/cpb.49.87

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.

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Indoles / chemistry*
Molecular Structure
Serotonin / analogs & derivatives
Serotonin / chemical synthesis*
Serotonin / chemistry
Spectrum Analysis
Tryptamines / chemistry*

Substances

Alkaloids
Indoles
Tryptamines
Serotonin
tryptamine