Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Phenampromide: Difference between pages

{{Short description|Chemical compound}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464199839

| IUPAC_name = ''N''-(1-Methyl-2-piperidin-1-ylethyl)-''N''-phenylpropanamide

| legal_AU = S9

| legal_BR = A1

| legal_BR_comment =.<ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>

| legal_CA = Schedule I

| legal_UK = ?

| legal_US = Schedule I

| legal_DE = Anlage I

| routes_of_administration = ?

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 129-83-9

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D12693

| smiles = CCC(N(C1=CC=CC=C1)[C@@H](CN2CCCCC2)C)=O

'''Phenampromide'''<ref>US3016382A N-substituted anilides and method of preparing the same</ref> 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<ref name="pmid14332652">{{cite journal | vauthors = Portoghese PS | title = Stereochemical Studies on Medicinal Agents II. Absolute Configuration of (-)-Phenampromide. | journal = Journal of Medicinal Chemistry | volume = 8 | pages = 147–50 | date = March 1965 | pmid = 14332652 | doi = 10.1021/jm00326a001 }}</ref> 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 [[enantiomer]]s 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.<ref>{{cite book | vauthors = Lenz GR, Evans SM, Walters DE, Hopfinger AJ |title=Opiates |date=1986 |publisher=Academic Press |location=Orlando |isbn=978-0-12-443830-9}}</ref> The most potent reported derivative is 4-hydroxy-4-phenyl phenapromide which displays analgesic activity some x150 greater than morphine.<ref>{{cite book | vauthors = Casy AF, Parfitt RT |title=Opiate Aalgesics Chemistry and Receptors |date=1986 |publisher=Springer Science+ Business Media |location=New York |isbn=978-1-4899-0587-1}}</ref>

:[[File:4-Phenylphenampromide_structure.png|200px|thumb|left|The [[fentanyl analogue]] 4-phenylphenampromide<ref>{{PubChem |3048547}}</ref>]]{{clear-left}}

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.<ref>{{cite web | title = Quotas - 2014 | url = http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }}</ref> 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 ==

{{Reflist|2}}

{{Opioidergics}}

[[Category:Synthetic opioids]]

[[Category:1-Piperidinyl compounds]]

[[Category:Propionamides]]

[[Category:Anilides]]

[[Category:Mu-opioid receptor agonists]]