Benzylmorphine

drugbox
IUPAC_name = 3-Benzyloxy-4,5α-epoxy-17-methyl-7-morphinen-6α-ol


width = 160
CAS_number = 14297-87-1
synonyms = Benzylmorphine, Peronine
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PubChem = 5362507
smiles = C16C4 [C@] 3(C2=C(C1)C=CC(=C2OC3 [C@H] (C=C4)O)OCC5=CC=CC=C5)CCN6C
DrugBank =
C = 24 | H = 25 | N = 1 | O = 3
molecular_weight = 375.46 g/mol
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legal_US = Schedule I
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Benzylmorphine (Peronine) is a semi-synthetic opiate narcotic introduced to the international market in 1897 and that of the United States very shortly thereafter. It is much like codeine, containing a benzyl group attached to the morphine molecule just as the methyl group creates codeine and the ethyl group creates ethylmorphine or dionine (used as a generic name for that drug just as peronine is for benzylmorphine). It is about 90 per cent as strong as codeine by weight.

Benzylmorphine is used in much the same way as codeine and ethylmorphine, primarily as a moderate strength analgesic, for eye surgery as a 1 to 2 per cent solution, and as a cough suppressant. It was available in the United States prior to 1914 and was still used until the 1960s, but fell into disuse once alternative opiate derivatives became preferred by doctors (i.e. hydrocodone as an analgesic and pholcodeine as a cough suppressant) Benzylmorphine is now a Schedule I Controlled Substance in the USA and is regulated internationally under UN drug conventions. [ Single Convention On Narcotic Drugs 1961 (United Nations) ]

Benzylmorphine is an active metabolite of the opioid analgesic myrophine, formed in the liver. It has a metabolic fate similar to that of codeine.

Benzylmorphine is used as the hydrochloride (free base conversion ratio 0.91) and methylsulphonate(0.80) and has a US DEA Administrative Controlled Substance Control Number of 9052.

References

* Merck Manual, 1900
* Merck Index, 1998
* [http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched1.htm United States Department of Justice, Drug Enforcement Administration: Controlled Substances in Schedule I]