Optical resolution of (+/-)-2,5-dimethyl-2'-hydroxy-9alpha- and -9beta-propyl-6,7-benzomorphans and their pharmacological properties.

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Abstrakt

Tytuł:: Optical resolution of (+/-)-2,5-dimethyl-2'-hydroxy-9alpha- and -9beta-propyl-6,7-benzomorphans and their pharmacological properties.
Autorzy:: Rice KC
Jacobson AE
Źródło:: Journal of medicinal chemistry [J Med Chem] 1976 Mar; Vol. 19 (3), pp. 430-2.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Publication: Washington Dc : American Chemical Society
Original Publication: [Easton, Pa.] : American Chemical Society, [c1963-
MeSH Terms:: Benzomorphans/*chemical synthesis
Morphinans/*chemical synthesis
Analgesics/chemical synthesis ; Animals ; Benzomorphans/analogs & derivatives ; Benzomorphans/pharmacology ; Haplorhini ; Humans ; Mice ; Morphine Dependence/physiopathology ; Optical Rotation ; Stereoisomerism ; Substance-Related Disorders/etiology
Substance Nomenclature:: 0 (Analgesics)
0 (Benzomorphans)
0 (Morphinans)
Entry Date(s):: Date Created: 19760301 Date Completed: 19760525 Latest Revision: 20190709
Update Code:: 20240104
DOI:: 10.1021/jm00225a021
PMID:: 815550
: Czasopismo naukowe

The levo and dextro isomers of 2,5-dimethyl-2'-hydroxy-9alpha- and -9beta-propyl-6,7-benzomorphans have been prepared. The analgesic potency and physical dependence capacity of the optical isomers and their racemic parents were determined. The 9alpha-propyl levo isomer was analgesically equipotent with morphine; the 9beta-propyl levo isomer was considerably more potent subcutaneously and equipotent orally. None of the optical isomers suppressed the withdrawal syndrome; the 9beta-propyl levo isomer exacerbated the withdrawal syndrome.

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