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Proheptazine

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From Wikipedia, the free encyclopedia

Opioid analgesic drug

Pharmaceutical compound

Proheptazine
Clinical data

ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs)^[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name 1,3-Dimethyl-4-phenylazepan-4-yl propionate
CAS Number	77-14-5
PubChemCID	60969
ChemSpider	54931^Y
UNII	S23189WW7E
KEGG	D12677^Y
CompTox Dashboard(EPA)	DTXSID50861628
ECHA InfoCard	100.000.916
Chemical and physical data
Formula	C₁₇H₂₅NO₂
Molar mass	275.392 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OC2(c1ccccc1)CCCN(C)CC2C)CC
InChI InChI=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^Y Key:ZXWAUWBYASJEOE-UHFFFAOYSA-N^Y
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Proheptazine is anopioid analgesic related topethidine. It was invented in the 1960s.^[2]

Proheptazine produces similar effects to other opioids,^[3] includinganalgesia,sedation,euphoria,dizziness andnausea.

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).^[4]^[5]

References

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^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
^Diamond J, Bruce WF, Tyson FT (January 1964). "Synthesis and Properties of the Analgesic DL-α-1,3-dimethyl-4-phenyl-4-propionoxyazacycloheptane (Proheptazine)".Journal of Medicinal Chemistry.7:57–60.doi:10.1021/jm00331a013.PMID 14186026.
^Finney ZG, Riley TN (August 1980). "4-Anilidopiperidine analgesics. 3. 1-Substituted 4-(propananilido)perhydroazepines as ring-expanded analogues".Journal of Medicinal Chemistry.23 (8):895–9.doi:10.1021/jm00182a016.PMID 7190616.
^"Quotas - 2014".Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.
^"Conversion Factors for Controlled Substances".Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.