Phenampromide

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	129-83-9 ;
PubChem CID	8523;
ChemSpider	16735960 ;
UNII	0600L2M6EZ;
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 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. Phenampromide produces similar effects to other opioids, 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.^[5] 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

^ 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.
^ US 3016382, "N-substituted anilides and method of preparing the same"
^ Lenz GR, Evans SM, Walters DE, Hopfinger AJ (1986). Opiates. Orlando: Academic Press. ISBN 978-0-12-443830-9.
^ US 3518274, "Phenyl substituted n-(2-aminoethyl)-n-benzylamides"
^ "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.

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[pmid14332652-1] 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] "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.

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