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 50 mg codeine ≈ 60 mg phenampromide. Tests on the 2 isomers showed that all of the analgesic effects were caused by the (S) isomer. Introduction of a phenyl group to the 4-position of the piperidine-ring produces a drug 60-fold more potent than morphine.^[4] The most potent reported derivative is 4-hydroxy-4-phenyl phenapromide which displays analgesic activity some x150 greater than morphine.^[5]

Phenampromide

Clinical data
Routes of administration	?
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs) .[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: ? US: Schedule I
Identifiers
IUPAC name N-(1-methyl-2-piperidin-1-ylethyl)-N-phenylpropanamide
CAS Number	129-83-9 N
PubChem CID	8523
ChemSpider	16735960 Y
UNII	0600L2M6EZ
KEGG	D12693 Y
CompTox Dashboard (EPA)	DTXSID10911012
ECHA InfoCard	100.004.517
Chemical and physical data
Formula	C17H26N2O
Molar mass	274.408 g·mol−1
3D model (JSmol)	Interactive image
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 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. Casy AF, Parfitt RT (1986). Opiate Aalgesics Chemistry and Receptors. New York: Springer Science+ Business Media. ISBN 978-1-4899-0587-1.
6. "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.