Benzylmorphine

Title: Benzylmorphine
CAS Registry Number: 14297-87-1
CAS Name: 7,8-Didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)morphinan-6-ol
Molecular Formula: C24H25NO3
Molecular Weight: 375.46
Percent Composition: C 76.77%, H 6.71%, N 3.73%, O 12.78%
Literature References: Prepn from morphine and benzyl chloride in the presence of sodium ethylate: DE 91813 (1897 to E. Merck), Frdl. 4, 1245; from morphine and benzyldimethylphenylammonium hydroxide: Rodionow, Bull. Soc. Chim. Fr. [4] 45, 109 (1929). Properties of hydrochloride: Dott, Pharm. J. 115, 757 (1925).
Properties: Needles from water, prisms or platelets from ether, chloroform. mp 132°. Soluble in 2500 parts cold water, more sol in boiling water; 1.6 parts dissolves in 100 parts ether; readily sol in 50% alcohol, benzene.
Melting point: mp 132°
Derivative Type: Hydrochloride
Additional Names: Peronine
Molecular Formula: C24H25NO3.HCl
Molecular Weight: 411.92
Percent Composition: C 69.98%, H 6.36%, N 3.40%, O 11.65%, Cl 8.61%
Properties: Monohydrate, needles from water. Sol at 15° in 133 parts water, 218 parts 95% alcohol, 390 parts chloroform, 100 parts methanol; slightly sol in abs alcohol; very slightly sol in ether, acetone, isoamyl alcohol.
NOTE: This is a controlled substance (opium derivative): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Benzylsulfamide Benzylurea Bephenium Hydroxynaphthoate Bepotastine Bepridil

Benzylmorphine
Benzylmorphine.svg
Systematic (IUPAC) name
(5α,6α)-3-(benzyloxy)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
Clinical data
Legal status Schedule I (US) Narcotic Schedule I (UN)
Identifiers
CAS number 14297-87-1 YesY
ATC code None
PubChem CID 5362507
DrugBank DB01573
ChemSpider 4515062 YesY
Synonyms Benzylmorphine, Peronine, 3-Benzyloxy- 4,5α-epoxy- 17-methyl- 7-morphinen-6α-ol
Chemical data
Formula C24H25NO3 
Mol. mass 375.46 g/mol
 YesY (what is this?)  (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.[1]

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.