Phenomorphan

{{Short description|Chemical compound}} {{Drugbox | verifiedrevid = 447927638 | IUPAC_name = 17-(2-Phenylethyl)morphinan-3-ol | image = Phenomorphan.svg | image_class = skin-invert-image | width = 230px | image2 = Phenomorphan 3D BS.png | image_class2 = bg-transparent | width2 = 230px

| tradename = | pregnancy_AU =  | pregnancy_US =  | pregnancy_category = | legal_AU = S9 | legal_BR = A1 | 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=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}</ref> | legal_CA = Schedule I | legal_UK = Class A | legal_US = Schedule I | legal_DE = Anlage I | routes_of_administration =

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 468-07-5 | ATC_prefix = none | ATC_suffix = | PubChem = 5362458 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 16735962 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 26HXE4B73P | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D12688

| C=24 | H=29 | N=1 | O=1 | smiles = Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@H]12)c4c3)CCc5ccccc5 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C24H29NO/c26-20-10-9-19-16-23-21-8-4-5-12-24(21,22(19)17-20)13-15-25(23)14-11-18-6-2-1-3-7-18/h1-3,6-7,9-10,17,21,23,26H,4-5,8,11-16H2/t21-,23+,24+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CFBQYWXPZVQQTN-QPTUXGOLSA-N | synonyms = <small>(-)-3-hydroxy- ''N''- (2-phenylethyl) morphinan</small> }}

'''Phenomorphan'''<ref>{{ cite patent | country = US | number = 2885401 | status = patent | title = Process for making morphinan derivatives and products available thereby | pubdate = 1956-03-22 | gdate = 1959-05-05 | inventor = Grussner A, Hellerbach J, Schnider O }}</ref> is an opioid analgesic. It is not currently used in medicine, but has similar side-effects to other opiates, which include itching, nausea and respiratory depression.

Phenomorphan is a highly potent drug due to the N-phenethyl group, which boosts affinity to the μ-opioid receptor, and so phenomorphan is around 10x more potent than levorphanol, which is itself 6-8x the potency of morphine. Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings<ref>{{ cite patent | country = US | number = 2970147 | status = patent | title = 3-hydroxy-N-(heterocyclic-ethyl)-morphinans | pubdate = 1958-11-26 | gdate = 1961-01-31 | inventor = Andre Grussner, Joseph Hellerbach, Otto Schnider }}</ref> are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than levorphanol, respectively.<ref>{{cite book | vauthors = Hellerbach J, Schnider O, Besendorf H, Pellmont B | series= International series of monographs on organic chemistry | title = Synthetic Analgesics: Part IIA. Morphinans | publisher = Pergamon Press | year = 1966 | url=https://www.scribd.com/doc/39966259/Synthetic-Analgesics-1966-Part-IIA-Morphinans }}</ref>

==References== {{Reflist|2}}

Category:Synthetic opioids Category:Morphinans Category:Hydroxyarenes Category:Mu-opioid receptor agonists