Pethidine intermediate A

Pethidine intermediate A is a 4-phenylpiperidine 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,[1] 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). [2]

Pethidine intermediate A

Clinical data
Routes of administration	N/A
ATC code	none
Legal status
Legal status	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
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
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See also

• Moramide intermediate
• Methadone intermediate
• Pethidine intermediate B (norpethidine)
• Pethidine intermediate C (pethidinic acid)

References

1. Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML. Synthesis and Biological Evaluation of Meperidine Analogues at Monoamine Transporters. Journal of Medicinal Chemistry. 2005; 48:1336-1343.
2. http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html