Proheptazine
{{Short description|Opioid analgesic drug}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| verifiedrevid = 447991032
| IUPAC_name = 1,3-Dimethyl-4-phenylazepan-4-yl propionate
| image = Proheptazine.svg
| image_class = skin-invert-image
| width = 200
| image2 =
| 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 =
| legal_US = Schedule I
| legal_DE = Anlage I
| routes_of_administration =
| bioavailability =
| protein_bound =
| elimination_half-life =
| excretion =
| CAS_number = 77-14-5
| ATC_prefix = none
| ATC_suffix =
| PubChem = 60969
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 54931
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S23189WW7E
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D12677
| C=17 | H=25 | N=1 | O=2
| smiles = O=C(OC2(c1ccccc1)CCCN(C)CC2C)CC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H25NO2/c1-4-16(19)20-17(15-9-6-5-7-10-15)11-8-12-18(3)13-14(17)2/h5-7,9-10,14H,4,8,11-13H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZXWAUWBYASJEOE-UHFFFAOYSA-N
| synonyms =
}}
Proheptazine is an opioid analgesic related to pethidine. It was invented in the 1960s.{{cite journal | vauthors = Diamond J, Bruce WF, Tyson FT | title = Synthesis and Properties of the Analgesic DL-α-1,3-dimethyl-4-phenyl-4-propionoxyazacycloheptane (Proheptazine). | journal = Journal of Medicinal Chemistry | volume = 7 | pages = 57–60 | date = January 1964 | pmid = 14186026 | doi = 10.1021/jm00331a013 }}
Proheptazine produces similar effects to other opioids,{{cite journal | vauthors = Finney ZG, Riley TN | title = 4-Anilidopiperidine analgesics. 3. 1-Substituted 4-(propananilido)perhydroazepines as ring-expanded analogues | journal = Journal of Medicinal Chemistry | volume = 23 | issue = 8 | pages = 895–9 | date = August 1980 | pmid = 7190616 | doi = 10.1021/jm00182a016 }} including analgesia, sedation, euphoria, dizziness and nausea.
In the United States it is a Schedule I Narcotic controlled substance with an ACSCN of 9643 and a 2013 annual aggregate manufacturing quota of zero. The salts in use are the citrate (free base conversion ratio 0.589), hydrobromide (0.773), and hydrochloride (0.883).{{cite web | title = Quotas - 2014 | url = http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }}{{cite web | title = Conversion Factors for Controlled Substances | url = http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }}