Phenampromide

Phenampromide
Clinical data
Routes of; administration	?
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs) .; 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 ;
PubChem CID	8523;
ChemSpider	16735960 ;
UNII	0600L2M6EZ;
KEGG	D12693 ;
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 ; Key:DHTRHEVNFFZCNU-OAHLLOKOSA-N ;
	(what is this?) (verify)

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 research found that 60 mg of phenampromide is equivalent to about 50 mg of codeine. Tests on its two enantiomers 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 produces similar effects to fentanyl, including analgesia, sedation, dizziness and nausea.

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.^[7] 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

^ 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.
^ US3016382A N-substituted anilides and method of preparing the same
^ 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.
^ Lenz GR, Evans SM, Walters DE, Hopfinger AJ (1986). Opiates. Orlando: Academic Press. ISBN 978-0-12-443830-9.
^ Casy AF, Parfitt RT (1986). Opiate Aalgesics Chemistry and Receptors. New York: Springer Science+ Business Media. ISBN 978-1-4899-0587-1.
^ CID 3048547 from PubChem
^ "Quotas - 2014". 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.

[2] US3016382A N-substituted anilides and method of preparing the same

[pmid14332652-3] 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] CID 3048547 from PubChem

[7] "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.

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