Chemistry:Phenampromide
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| Formula | C17H26N2O |
| Molar mass | 274.408 g·mol−1 |
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Phenampromide[1] 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[2] 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.[3] The most potent reported derivative is 4-hydroxy-4-phenyl phenapromide which displays analgesic activity some x150 greater than morphine.[4]
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.[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 fentanyl.
References
- ↑ US3016382A N-substituted anilides and method of preparing the same
- ↑ "Stereochemical Studies on Medicinal Agents II. Absolute Configuration of (-)-Phenampromide.". Journal of Medicinal Chemistry 8: 147–50. March 1965. doi:10.1021/jm00326a001. PMID 14332652.
- ↑ Opiates. Orlando: Academic Press. 1986. ISBN 978-0-12-443830-9.
- ↑ Opiate Aalgesics Chemistry and Receptors. New York: Springer Science+ Business Media. 1986. ISBN 978-1-4899-0587-1.
- ↑ "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm.
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