Phenampromide

---

title: "Phenampromide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["synthetic-opioids", "1-piperidinyl-compounds", "propionamides", "anilides", "mu-opioid-receptor-agonists"] description: "Chemical compound" topic_path: "general/synthetic-opioids" source: "https://en.wikipedia.org/wiki/Phenampromide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464199839 | IUPAC_name = N-(1-Methyl-2-piperidin-1-ylethyl)-N-phenylpropanamide | image = Phenampromide.svg | image_class = skin-invert-image | width = 180

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = S9 | legal_BR = A1 | legal_BR_comment =. | legal_CA = Schedule I | legal_UK = ? | legal_US = Schedule I | legal_DE = Anlage I | routes_of_administration = ?

| bioavailability = | protein_bound = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 129-83-9 | ATC_prefix = none | ATC_suffix = | PubChem = 8523 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 16735960 | UNII_Ref = | UNII = 0600L2M6EZ | KEGG_Ref = | KEGG = D12693 | C=17 | H=26 | N=2 | O=1 | smiles = CCC(N(C1=CC=CC=C1)C@@HC)=O | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = DHTRHEVNFFZCNU-OAHLLOKOSA-N | synonyms =

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 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. The most potent reported derivative is 4-hydroxy-4-phenyl phenapromide which displays analgesic activity some x150 greater than morphine.

:[[File:4-Phenylphenampromide_structure.png|class=skin-invert-image|200px|thumb|left|The [[fentanyl analogue]] 4-phenylphenampromide]]

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. 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

References

1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
2. US3016382A N-substituted anilides and method of preparing the same
3. (March 1965). "Stereochemical Studies on Medicinal Agents II. Absolute Configuration of (-)-Phenampromide.". Journal of Medicinal Chemistry.
4. (1986). "Opiates". Academic Press.
5. (1986). "Opiate Aalgesics Chemistry and Receptors". Springer Science+ Business Media.
6. {{PubChem. 3048547
7. , GB963820 (1964 to Miles Laboratories, Bayer Corp).
8. "Quotas - 2014". Drug Enforcement Agency, U.S. Department of Justice.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::