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 = {{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}}
| legal_CA = Schedule I
| legal_UK = Class A
| legal_US = Schedule I
| legal_DE = Anlage I
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| 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 = (-)-3-hydroxy- N- (2-phenylethyl) morphinan
}}
Phenomorphan{{ 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
}} 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{{ 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
}} 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.{{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 }}