Nalorphine has less of an analgesic effect than morphine; however, it does not have much value as an independent analgesic. It is used as an antagonist to narcotic analgesics. It eliminates suppression of the respiratory center, bradycardia, and vomiting caused by opiate receptor agonists.
Nalorphine was the first compound used for narcotic (heroin in particular) overdose treatment; however, it exhibits a number of side effects such as visual hallucinations, and therefore its use is prohibited in some countries. The most popular synonym for this drug is narkan.
Pentazocine: Pentazocine, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol (3.1.81), is a derivative of benzomorphane. Pentazocine is synthesized starting from 3,4-dimethylpyridine. It undergoes a reaction with methyl iodide to give 1,3,4-trimethylpyridinium iodide (3.1.76), which is reacted with 4-methoxybenzyl magnesiumchloride, forming 2-methoxybenzyl-3,4-dimethyl-1,2-dihydropyridine (3.1.77). The double bond on C5 of the resulting compound is hydrogenated using a palladium catalyst, giving 3-methoxybenzyl-3,4-dimethyl-1,2,3,4-tetrahydropyridine (3.1.78). The resulting product undergoes intramolecular alkylation and simultaneous demethyla-tion of the ether bond by hydrobromic acid, which results in the formation of 2-hydroxy-2,5,9-trimethylbenzo-6-morphane (3.1.79), which undergoes N-demethylation by cyanogen bromide to form 2-hydroxy-5,9-dimethylbenzo-6-morphane-N-normetazocine (3.1.80). Alkylation of the resulting product by 1-bromo-3-methyl-2-butene gives penta-zocine [49,50].
CH3 CH3 ch3
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