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Proheptazine
Clinical data
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs); 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;
PubChem CID	60969;
ChemSpider	54931 ;
UNII	S23189WW7E;
KEGG	D12677 ;
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 ; Key:ZXWAUWBYASJEOE-UHFFFAOYSA-N ;
	(verify)

Proheptazine is an opioid analgesic related to pethidine. It was invented in the 1960s.^[2]

Proheptazine produces similar effects to other opioids,^[3] 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).^[4]^[5]

References

^ 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. Retrieved 2023-08-16.
^ 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.

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[1] 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. Retrieved 2023-08-16.

[pmid14186026-2] 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.

[pmid7190616-3] 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.

[4] "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.

[5] "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.

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