Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Regular Articles
The Chemistry of Indoles. CIII.1) 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
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Keywords: 1-hydroxytryptamine, nucleophilic substitution reaction, serotonin, bufotenine, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, lespedamine
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2001 Volume 49 Issue 1 Pages 87-96

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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.

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© 2001 The Pharmaceutical Society of Japan
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