Neuroleptic agents of the benzocycloheptapyridoisoquinoline series. 1. Syntheses and stereochemical and structural requirements for activity of butaclamol and related compounds

The syntheses and the structural and stereochemical requirements for antagonism of (+)-amphetamine-induced sterotypy are described for a series of benzocycloheptapyridoisoquinoline derivatives. One of these compounds, (plus or minus)-(4a,13b-trans)[3(OH),13b(H)-trans[-3-tert-butyl-2,3,4,4a,8,9,13b,1...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1975-02, Vol.18 (2), p.185-188
Main Authors: Bruderlein, Francois T, Humber, Leslie G, Voith, Katherine
Format: Article
Language:English
Subjects:
Amphetamine - antagonists & inhibitors
Amphetamine - pharmacology
Animals
Behavior, Animal - drug effects
Dibenzocycloheptenes - chemical synthesis
Dibenzocycloheptenes - pharmacology
Humans
Male
Molecular Conformation
Motor Activity - drug effects
Quinolizines - chemical synthesis
Quinolizines - pharmacology
Rats
Stereoisomerism
Stereotyped Behavior - drug effects
Structure-Activity Relationship
Tranquilizing Agents - chemical synthesis
Tranquilizing Agents - pharmacology
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Summary:The syntheses and the structural and stereochemical requirements for antagonism of (+)-amphetamine-induced sterotypy are described for a series of benzocycloheptapyridoisoquinoline derivatives. One of these compounds, (plus or minus)-(4a,13b-trans)[3(OH),13b(H)-trans[-3-tert-butyl-2,3,4,4a,8,9,13b,14-octahydro-1H-benzo[6,7]cyclohepta[1,2,3-de]pyrido[2,1-a]isoquinolin-3ol hydrochloride (butaclamol hydrochloride, USAN), is currently being studied in man. The relationship between structure and antiamphetamine activity in this class of compounds is discussed.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00236a016