Phenampromide

Phenampromide[2] 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[3] by American Cyanamid Co. 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[4] a 4-phenyl group added to the piperidine-ring produces a drug some x60 morphine. The potency derives from the fact that it similar in structure to 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
Routes of
administration		?
ATC code
  • none
Legal status
Legal status
Identifiers
  • N-(1-methyl-2-piperidin-1-ylethyl)-N-phenylpropanamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.004.517
Chemical and physical data
FormulaC17H26N2O
Molar mass274.408 g·mol−1
3D model (JSmol)
  • CCC(N(C1=CC=CC=C1)[C@@H](CN2CCCCC2)C)=O
  • 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 checkY
  • Key:DHTRHEVNFFZCNU-OAHLLOKOSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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

The fentanyl analogue 4-Phenylphenampromide (Pubchem ID # 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 fentanyl.

References
  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.
  2. US3016382A N-substituted anilides and method of preparing the same
  3. 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.
  4. Lenz GR, Evans SM, Walters DE, Hopfinger AJ (1986). Opiates. Orlando: Academic Press. ISBN 978-0-12-443830-9.
  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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