Benzylmorphine

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Image:Benzylmorphine.png
Benzylmorphine
Systematic (IUPAC) name
3-Benzyloxy-4,5α-epoxy-17-methyl-7-morphinen-6α-ol
Identifiers
CAS number	14297-87-1
ATC code	?
PubChem	5362507
Chemical data
Formula	C24H25NO3
Mol. mass	375.46 g/mol
Synonyms	Benzylmorphine, Peronine
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule I(US)
Routes	?

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 benzoyl 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 dihydrocodeine, primarily as a moderate strength analgesic and 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. ^[1]

References

• Merck Manual, 1900
• Merck Index, 1998
• United States Department of Justice, Drug Enforcement Administration: Controlled Substances in Schedule I

v • d • e Opioids (N02A)
Opiate derivatives	Whole Opium Preparations Dover's Powder • Granulated Opium • Laudanum • Mithridate • Opium • Paregoric • Poppy Straw Concentrate • Poppy tea • Powdered Opium • Raw Opium • Smoking Opium Natural Opiates Codeine • Morphine • Narceine • Noscapine • Omnopon • Oripavine • Pantopon • Papaveretum • Pseudomorphine • Tetrapon • Thebaine Semisynthetics 2,4-Dinitrophenylmorphine • 14-Hydroxyazidomorphine • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 6-Ketonalbuphine • 6-Methyldihydromorphine • 6-Methylenedihydrodesoxymorphine • 6-Methylene-14-hydroxydihydrodesoxymorphine • 8,14-Dihydroxydihydromorphinone • Acetylcodeine • Acetyldihydrocodeine • Acetylmorphone • Azidocodeine • Azidomorphine • Benzylmorphine • Chloromorphide • Clocinnamox • Codeine • Codeinone • Codorphone • Codoxime • Desocodeine • Desomorphine • Diacetyldihydromorphine • Dihydrocodeine • Dihydrocodeinone enol acetate • Dihydrohydroxycodeinone • Dihydrodesoxymorphine • Dihydroheroin • Dihydroheterocodeine • Dihydroisocodeine • Dihydromorphine • Dibutanoylmorphine • Dipropanoylmorphine • Ethyldihydromorphinone • Ethyldihydromorphine • Ethylmorphine • Heroin (Diamorphine) • Heroin-7,8-Oxide • Heterocodeine • Hydrocodone • Hydromorphinol • Hydromorphone • Isocodeine • Methyldesorphine • Methyldihydromorphine • Methylnaltrexone • Metopon • Morphinone • Myrophine • N-Phenethyl-14-ethoxymetopon • Nalbuphine • Nalfurafine • Nalmefene • Nalodeine • Nalorphine • Naloxone • Naltrexone • Naltrindole • Nicocodeine • Nicodicodeine • Nicomorphine • Oxycodone • Oxymorphone • Pholcodine • Semorphone • Thebacon Opiate metabolites Codeine-N-Oxide • Morphine-3-glucuronide • Morphine-6-glucuronide • Monoacetylmorphine • Morphine-N-Oxide • Naltrexol • Norcodeine • Normorphine
Morphinans	Aknadinine • Butorphanol • Cyclorphan • Cyprodime • Dextro-3-hydroxy-N-allylmorphinan • Dextromethorphan • Dextrorphan • Dimemorfan • Drotebanol • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan • Salutaridine (Sinoacutine) • Sinococuline • Sinomenine (Cocculine)
Benzomorphans	5,9-DEHB • Anazocine • Bremazocine • Cogazocine • Cyclazocine • Dezocine • Eptazocine • Etazocine • Ethylketocyclazocine • Fluorophen • Ketazocine • Metazocine • Pentazocine • Phenazocine • Quadazocine • Thiazocine
4-Phenylpiperidines	Pethidines (Meperidines) Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Hydroxymethoxypethidine • Morpheridine • Oxpheneridine (Carbamethidine) • Meperidine-N-Oxide • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine Prodines Allylprodine • α-meprodine • α-prodine • β-meprodine • β-prodine • Isopromedol • Meprodine • MPPP • PEPAP • Prodine • Prosidol • Trimeperidine (Promedol) Ketobemidones Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone Others Alvimopan • Loperamide • Picenadol
Open Chain Opioids	Amidones Dextromethadone • Dipipanone • Hexalgon • Isomethadone • Levomethadone • Methadone • Methadone intermediate • Normethadone • Norpipanone • Phenadoxone (Heptazone) • Pipidone Methadols Acetylmethadol • α-methadol • α-acetylmethadol • β-methadol • β-acetylmethadol • Dimepheptanol (Racemethadol) • Levo-α-acetylmethadol • Noracymethadol Moramides Dextromoramide • Levomoramide • Moramide intermediate • Racemoramide Thiambutenes Thiambutene • Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Tipepidine Phenalkoxams Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene Ampromides Diampromide • Phenampromide • Propiram Others IC-26 • Lefetamine • R-4066
Anilidopiperidines	3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • Benzylfentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thenylfentanyl • Thiofentanyl • Trefentanil
Oripavine derivatives	7-PET • Acetorphine • Alletorphine • BU-48 • Buprenorphine • Cyprenorphine • Dihydroetorphine • Diprenorphine • Etorphine • N-cyclopropylmethyl-noretorphine • Nepenthone • Norbuprenorphine • Thevinone
Phenazepines	Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine
Pirinitramides	Bezitramide • Piritramide
Benzimidazoles	Clonitazene • Etonitazene
Indoles	7-Acetoxymitragynine • 7-Hydroxymitragynine • Akuammidine • Akuammine • Eseroline • Ibogaine • Mitragynine • ψ-Akuammigine
Diphenylmethylpiperazines	BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80
Opioid Peptides	Casomorphin • DADLE • DALDA • DAMGO • Dermenkephalin • Dermorphin • Deltorphin • DPDPE • Dynorphin • Endomorphin • Endorphin • Enkephalin • TRIMU 5
Others	4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol • C-8813 • Ciramadol • Enadoline • Faxeladol • Herkinorin • JTC-801 • Methopholine • NNC 63-0532 • Noscapine/Narcotine • O-Desmethyltramadol • Salvinorin A • RWJ-394,674 • Tapentadol • Tifluadom • Tilidine • Tramadol • Viminol • W-18 • Zipeprol
Narcotic Antagonists	5'-Guanidinonaltrindole • β-Funaltrexamine • Binaltorphimine • Cyclazocine • Cyclohexyl-alpha-phenethylallylamine • Diprenorphine • M5050 • Levallorphan • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexone • Naltrindole • Norbinaltorphimine • Oxilorphan

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .