piminodine
{{Short description|Opioid analgesic drug}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 400852912
| IUPAC_name = ethyl 1-(3-anilinopropyl)-4-phenylpiperidine-4-carboxylate
| image = Piminodine.svg
| image_class = skin-invert-image
| width = 160
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| 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 =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 13495-09-5
| ATC_prefix = none
| ATC_suffix =
| PubChem = 21950
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 20628
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 3IIX447HWS
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D12683
| C = 23
| H = 30
| N = 2
| O = 2
| smiles = O=C(OCC)C3(c1ccccc1)CCN(CCCNc2ccccc2)CC3
| StdInChI2 = 1/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3
| StdInChIKey2 = PXXKIYPSXYFATG-UHFFFAOYAI
| StdInChIKey2_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PXXKIYPSXYFATG-UHFFFAOYSA-N
| synonyms =
}}
Piminodine (Alvodine) is an opioid analgesic that is an analogue of pethidine (meperidine).{{cite journal | vauthors = Sim E, Dimoglo A, Shvets N, Ahsen V | title = Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics | journal = Current Medicinal Chemistry | volume = 9 | issue = 16 | pages = 1537–45 | date = August 2002 | pmid = 12171562 | doi = 10.2174/0929867023369510 }} It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with hydroxyzine to intensify the effects. The duration of action is 2–4 hours; 7.5–10 mg via the subcutaneous route is the most common starting dose, being equal to 80–100 mg of pethidine, 40–60 mg of alphaprodine and 10 mg of morphine. Oral formulations were also available.
Piminodine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening.{{cite journal | vauthors = Dekornfeld TJ, Lasagna L | title = The analgesic potency of piminodine (alvodine) | journal = Journal of Chronic Diseases | volume = 12 | issue = 2| pages = 252–7 | date = August 1960 | pmid = 13815493 | doi = 10.1016/0021-9681(60)90102-8 }}{{cite journal | vauthors = Woods LA, Deneau GA, Bennett DR, Domino EF, Seevers MH | title = A comparison of the pharmacology of two potent analgesic agents, piminodine (Win 14,098-2) and Win 13,797, with morphine and meperidine | journal = Toxicology and Applied Pharmacology| volume = 3 | pages = 358–79 | date = May 1961 | pmid = 13786579| doi = 10.1016/0041-008x(61)90072-2 | hdl = 2027.42/32367 | hdl-access = free }}