Benzylmorphine

Benzylmorphine

Systematic (IUPAC) name
(5α,6α)-3-(benzyloxy)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
Clinical data
Legal status	CA: Schedule I DE: Anlage I (Controlled) US: Schedule I UN: Narcotic Schedule I
Identifiers
CAS Number	14297-87-1 Y
ATC code	none
PubChem	CID: 5362507
DrugBank	DB01573 Y
ChemSpider	4515062 Y
Synonyms	Benzylmorphine, Peronine, 3-Benzyloxy- 4,5α-epoxy- 17-methyl- 7-morphinen-6α-ol
Chemical data
Formula	C24H25NO3
Molecular mass	375.46 g/mol
SMILES O[C@H]2\C=C/[C@H]6[C@@H]5N(CC[C@@]61c4c(O[C@H]12)c(OCc3ccccc3)ccc4C5)C
InChI InChI=1S/C24H25NO3/c1-25-12-11-24-17-8-9-19(26)23(24)28-22-20(27-14-15-5-3-2-4-6-15)10-7-16(21(22)24)13-18(17)25/h2-10,17-19,23,26H,11-14H2,1H3/t17-,18+,19-,23-,24-/m0/s1 Y Key:RDJGWRFTDZZXSM-RNWLQCGYSA-N Y
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Benzylmorphine (Peronine) is a semi-synthetic opioid narcotic introduced to the international market in 1896 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.

This drug, the benzyl ether of morphine, should not be cofused with dibenzoylmorphine, an ester of morphine comparable to heroin. Another morphine ether developed around the same time, benzyldihydromorphine, saw some clinical use in the opening years of the 20th Century. The ethers of morphine and codeine as well as dihydromorphine and dihydrocodeine number close to 100 and include such obscure opioids as formylallopseudoisocodeine.

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 codeine as a cough suppressant) Benzylmorphine is now a Schedule I Controlled Substance in the USA and is regulated internationally under UN drug conventions.

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
• United States Department of Justice, Drug Enforcement Administration: Controlled Substances in Schedule I