Benzazocines benzomorphanes

A series of unusual amidinium benzomorphans has been described by Strauss et a/.<53 55) where some members of the series exhibit narcotic antagonist properties. Their synthesis involves a meta bridging process of di- and trinitronaphthalenes (116) with a-phenyl N,N-dimethylacetamidine (117) to produce two isomeric benzazocine amidinium nitronates as their a-phenyl-N,N-dimethylacetamidinium salts (AmH+). The benzomorphan 118 is formed in ethanolic solution, whereas the isomeric benzazocine (119) results from reaction in dimethylsulfoxide. 

SYNS 2-DIMETHYL LLYI 5,9-DIMETHY1 2 -HYDRO-XYBENZOMORPHAN 2-(3,3-DIMETHYLALLYL)-2, 2 -HYDROXY-5,9-DlMETHYL-6,7-BENZOMORPHAN FORTALGESIC FORTALIN FORTRAL 1,2,3,4,5,6-HEXAHYDRO-6,ll-DIMETHYI 3-(3-METHYL-2-BUTENYL)-2,6-METHANO-3-BENZAZOCINE 2 -HYDROXY-5,9-DIMETHYL-2-(3,3-DIMETHYLALLYL)-6,7-BENZOMORPHAN dl-2 -HYDROXV-5,9-DIMETHYI 2-(3,3-DIMETH i LALLYL)-6,7-BENZOMORPHAN II-C-2... 

Pentazocine, USP. Pentazocine. 1.2.3.4.S.6-hcubv-dro-cfs-6,11 -dimethyl-3-(3-mc ihyl-2-butenyl)-2.6-nKili ano3-benzazocin-8-ol. ci.v-2-dimethylallyl-5.9-dimcthyl-l -hydroxy-6,7-benzomorphan (Talwin). iKCurs as a uhic crystallinc powder that is insoluble in water and sparingh". soluble in alcohol. It forms a prly soluble hyclnx lilnidt salt, but is readily soluble as the lactate. 

Further structural simplification by elimination of the C ring of the morphinan structure yields the benzomorphans (see Fig. 7.21), which are also known as benzazocines. 

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