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Synthesis and pharmacology of metabolically stable tert-butyl ethers of morphine and levorphanol.

Abstract：

:3-O-tert-Butylmorphine (5) was prepared from 6-O-acetylmorphine (3) via alkylation with N,N-dimethylformamide di-tert-butyl acetal, followed by hydrolytic removal of the 3-(dimethylamino)-2-propenoate group. The same process was used to prepare the tert-butyl ether of levorphanol (6), (-)-3-tert-butoxy-N-methylmorphinan (8). Both 5 and 8 exhibited in vitro affinity for the opiate receptor comparable to codeine and had analgesic properties in the writhing test. Only 5 exhibited activity in the tail-flick procedure and neither compound showed significant antitussive activity.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Mohacsi E,Leimgruber W,Baruth H

doi

10.1021/jm00352a037

subject

Has Abstract

pub_date

1982-10-01 00:00:00

pages

1264-6

issue

10

eissn

0022-2623

issn

1520-4804

journal_volume

25

pub_type

杂志文章

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