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Revision as of 01:02, 1 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits 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← Previous edit Latest revision as of 23:01, 28 October 2023 edit undoKimen8 (talk | contribs)Extended confirmed users5,112 edits Changing short description from "Chemical compound" to "Opioid analgesic and cough suppressant drug"Tag: Shortdesc helper 
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{{Short description|Opioid analgesic and cough suppressant drug}}
{{Drugbox {{Drugbox
| verifiedrevid = 443420069 | verifiedrevid = 447763389
| IUPAC_name = (5α,6α)-3-(benzyloxy)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol | IUPAC_name = (5α,6α)-3-(benzyloxy)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
| image = benzylmorphine.svg | image = benzylmorphine.svg
| alt = Structural formula

| width = 210
| image2 = Benzylmorphine molecule ball.png
| alt2 = Ball-and-stick model
| width2 = 230
<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
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| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_BR = A1
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule I
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = Schedule I | legal_US = Schedule I
| legal_DE = Anlage I
| legal_UN = N I
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 14297-87-1 | CAS_number = 14297-87-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 83C78V3OL9
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4515062 | ChemSpiderID = 4515062

<!--Chemical data--> <!--Chemical data-->
| C=24 | H=25 | N=1 | O=3 | C=24 | H=25
| N=1 | O=3
| molecular_weight = 375.46 g/mol
| smiles = O2\C=C/65N(CC61c4c(O12)c(OCc3ccccc3)ccc4C5)C | smiles = O2\C=C/65N(CC61c4c(O12)c(OCc3ccccc3)ccc4C5)C
| InChI = 1/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
| InChIKey = RDJGWRFTDZZXSM-RNWLQCGYBX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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| synonyms = Benzylmorphine, Peronine, 3-Benzyloxy- 4,5α-epoxy- 17-methyl- 7-morphinen-6α-ol | synonyms = Benzylmorphine, Peronine, 3-Benzyloxy- 4,5α-epoxy- 17-methyl- 7-morphinen-6α-ol
}} }}
⚫ '''Benzylmorphine''' ('''Peronine''') is a ] opioid ] introduced to the international market in 1896 and that of the United States very shortly thereafter. It is much like ], containing a benzyl group attached to the ] molecule just as the methyl group creates codeine and the ethyl group creates ] or dionine (used as a generic name for that drug just as peronine is for benzylmorphine). It is about 90% as strong as codeine by weight.


This drug, the benzyl ether of morphine, should not be confused with ], 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<ref>Report On the Committee On Drug Abuse 1929-1941</ref> and include such obscure opioids as formylallopseudoisocodeine.
⚫ '''Benzylmorphine''' ('''Peronine''') is a ] opiate ] introduced to the international market in 1896 and that of the United States very shortly thereafter. It is much like ], containing a benzyl group attached to the ] molecule just as the methyl group creates codeine and the ethyl group creates ] 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 ] and ], primarily as a moderate strength ], 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. ] as an analgesic and ] as a cough suppressant) Benzylmorphine is now a ] Controlled Substance in the USA and is regulated internationally under UN drug conventions.<ref> Single Convention On Narcotic Drugs 1961 (United Nations) </ref> Benzylmorphine is used in much the same way as ] and ], primarily as a moderate strength ], for eye surgery as a 1 to 2% 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. ] as an analgesic and ] as a cough suppressant) Benzylmorphine is now a ] Controlled Substance in the US and is regulated internationally under UN drug conventions.<ref>Single Convention On Narcotic Drugs 1961 (United Nations)</ref>


Benzylmorphine is an active metabolite of the opioid analgesic ], formed in the liver. It has a metabolic fate similar to that of codeine. Benzylmorphine is an active metabolite of the opioid analgesic ], 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. 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== ==Notes==
{{Reflist|2}}
<references />


==References==
* Merck Manual, 1900 * Merck Manual, 1900
* Merck Index, 1998 * Merck Index, 1998
* *


{{analgesic-stub}} {{Opioidergics}}

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