Phenampromide

Phenampromide is an opioid analgesic from the ampromide family of drugs, related to other drugs such as propiram and diampromide. It was invented in the 1960s[1] by American Cyanamid Co.[2] Although never given a general release, it was trialled and 50mg codeine ≈ 60mg phenampromide. Tests on the 2 isomers showed that all of the analgesic effects were caused by the (S) isomer. In the book[3] a 4-phenyl group added to the piperidine-ring produces a drug some x60 morphine.[4] The potency derives from the fact that it overlays fentanyl. Like fentanyl, the addition of a 4-hydroxy group to the 4-piperidylphenyl derivative increases potency to x150 morphine for the racemic compound[5]

Phenampromide
Clinical data
ATC code
  • none
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
Identifiers
IUPAC name
  • N-(1-methyl-2-piperidin-1-ylethyl)-N-phenylpropanamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.004.517
Chemical and physical data
FormulaC17H26N2O
Molar mass274.408 g·mol−1
3D model (JSmol)
SMILES
  • CCC(N(C1=CC=CC=C1)[C@@H](CN2CCCCC2)C)=O
InChI
  • InChI=1S/C17H26N2O/c1-3-17(20)19(16-10-6-4-7-11-16)15(2)14-18-12-8-5-9-13-18/h4,6-7,10-11,15H,3,5,8-9,12-14H2,1-2H3/t15-/m1/s1 Y
  • Key:DHTRHEVNFFZCNU-OAHLLOKOSA-N Y
 NY (what is this?)  (verify)

Phenampromide produces similar effects to other opioids, including analgesia, sedation, dizziness and nausea.

4-Phenylphenampromide, PMID 3048547

Phenampromide is in Schedule I of the Controlled Substances Act 1970 of the United States as a Narcotic with ACSCN 9638 with a zero aggregate manufacturing quota as of 2014. The free base conversion ratio for salts includes 0.88 for the hydrochloride.[6] It is listed under the Single Convention for the Control of Narcotic Substances 1961 and is controlled in most countries in the same fashion as is morphine.

References
  1. Portoghese PS (March 1965). "Stereochemical Studies on Medicinal Agents II. Absolute Configuration of (-)-Phenampromide". Journal of Medicinal Chemistry. 8: 147–50. doi:10.1021/jm00326a001. PMID 14332652.
  2. US 3016382, "N-substituted anilides and method of preparing the same"
  3. Lenz GR, Evans SM, Walters DE, Hopfinger AJ (1986). Opiates. Orlando: Academic Press. ISBN 978-0-12-443830-9.
  4. US 3518274, "Phenyl substituted n-(2-aminoethyl)-n-benzylamides"
  5. 'Opiate Analgesics - Chemistry and receptors' page 470.
  6. "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.



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