Pethidine intermediate A

Pethidine intermediate A
Clinical data
Routes of; administration	N/A
ATC code	none;
Legal status
Legal status	BR: Class A1 (Narcotic drugs); DE: Anlage II (Authorized trade only, not prescriptible); US: Schedule II; UN: Narcotic Schedule I;
Identifiers
	IUPAC name 1-methyl-4-phenylpiperidine-4-carbonitrile;
CAS Number	3627-62-1;
PubChem CID	62513;
ChemSpider	56289;
UNII	EL4L2474TY;
KEGG	C22687;
CompTox Dashboard (EPA)	DTXSID50189814 ;
ECHA InfoCard	100.020.771
Chemical and physical data
Formula	C13H16N2
Molar mass	200.285 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC(CC1)(C#N)c2ccccc2;
	InChI InChI=1S/C13H16N2/c1-15-9-7-13(11-14,8-10-15)12-5-3-2-4-6-12/h2-6H,7-10H2,1H3; Key:ZLFQTZYFXYOGLS-UHFFFAOYSA-N;
	(verify)

Pethidine intermediate A is a four-phenyl piperidine derivative that is a precursor to the opioid analgesic drug pethidine (meperidine). It is not known to have any analgesic activity in its own right, however other derivatives of pethidine with a 4-cyano group in place of the carboxylate ethyl ester have been found to be active,^[2] so pethidine intermediate A might also show opioid effects. It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9232. The 2014 annual manufacturing quota was 6 grammes (as an end product, presumably for research use).^[3]

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.
^ Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML (March 2005). "Synthesis and biological evaluation of meperidine analogues at monoamine transporters". Journal of Medicinal Chemistry. 48 (5): 1336–43. doi:10.1021/jm0401614. PMID 15743177.
^ "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.

[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.

[pmid15743177-2] Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML (March 2005). "Synthesis and biological evaluation of meperidine analogues at monoamine transporters". Journal of Medicinal Chemistry. 48 (5): 1336–43. doi:10.1021/jm0401614. PMID 15743177.

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

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[2]

[3]

See also

References