Misplaced Pages

Benzylmorphine

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 01:02, 1 September 2011 (Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 01:02, 1 September 2011 by CheMoBot (talk | contribs) (Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Benzylmorphine
Clinical data
Other namesBenzylmorphine, Peronine, 3-Benzyloxy- 4,5α-epoxy- 17-methyl- 7-morphinen-6α-ol
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • (5α,6α)-3-(benzyloxy)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.034.739 Edit this at Wikidata
Chemical and physical data
FormulaC24H25NO3
Molar mass375.46 g/mol g·mol
3D model (JSmol)
SMILES
  • O2\C=C/65N(CC61c4c(O12)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
  • Key:RDJGWRFTDZZXSM-RNWLQCGYSA-N
  (verify)

Benzylmorphine (Peronine) is a semi-synthetic opiate 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.

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

  1. Single Convention On Narcotic Drugs 1961 (United Nations)
Stub icon

This analgesic-related article is a stub. You can help Misplaced Pages by expanding it.

Categories: