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

{{Short description|Opioid analgesic}}

| Watchedfields = changed

| verifiedrevid = 464200012

| IUPAC_name = (2''R'',6''R'',11''R'')-6,11-Dimethyl-3-(2-phenylethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol

| image = Phenazocine2DCSD.svg

| width = 220px

| image2 = Phenazocine 3D BS.png

| width2 = 220px

| legal_AU = Schedule 9

| 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 = Class A

| legal_UK_comment = Withdrawn

| legal_DE = Anlage I

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 58073-76-0

| KEGG = C11790

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 391631

| smiles = C[C@H]1[C@H]2Cc3ccc(cc3[C@@]1(CCN2CCc4ccccc4)C)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3/t16-,21+,22+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZQHYKVKNPWDQSL-KNXBSLHKSA-N

'''Phenazocine''' (brand names '''Prinadol''', '''Narphen''') is an [[opioid analgesic]] [[pharmaceutical drug|drug]], which is related to [[pentazocine]] and has a similar profile of effects.<ref>{{cite patent | country = US | number = 2959594 | title = Iso-benzmorphan derivatives }}</ref>

Effects of phenazocine include analgesia and [[euphoria]], also may include [[dysphoria]] and [[hallucinations]] at high doses, most likely due to action at [[Kappa opioid receptor|κ-opioid]] and [[Sigma receptor|σ receptors]].<ref name="Harris">{{cite journal |vauthors=Harris LS, Pierson AK | title=Some Narcotic Antagonists in the Benzomorphan Series | journal=Journal of Pharmacology and Experimental Therapeutics |date=February 1964 | pages=141–8 | volume= 143| pmid=14163985}}</ref>

Phenazocine appears to be a much stronger analgesic with fewer side effects than pentazocine, probably due to a more favorable [[mu opioid receptor|μ]]/κ binding ratio. Phenazocine is a much more potent analgesic than pentazocine and other drugs in the benzomorphan series, most probably due to the presence of an ''N''-phenethyl substitution, which is known to boost μ-opioid activity in many classes of opioid analgesics.<ref name="Feinberg">{{cite journal |vauthors=Feinberg AP, Creese I, Snyder SH | title=The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists | journal=Proceedings of the National Academy of Sciences USA |date=November 1976 | pages=4215–9 | volume=73 | issue=11 | pmid=186791 | doi=10.1073/pnas.73.11.4215 | pmc= 431391| bibcode=1976PNAS...73.4215F | doi-access=free }}</ref> Also, it does not cause spasm of the [[sphincter of Oddi]], making it more suitable than morphine for the treatment of [[biliary]] or [[pancreatic]] pain.<ref name="Hopton">{{cite journal | author=Hopton D. | title=Double-blind clinical trial of the analgesic effects of phenazocine hydrobromide (Narphen) compared with morphine sulphate in patients with acute abdominal pain | journal=Gut |date=January 1971 | pages=51–4 | volume=12 | issue= 1 | pmid=4929685 | doi=10.1136/gut.12.1.51 | pmc=1411461}}</ref>

Regarding the two [[enantiomer]]s of phenazocine, (''R'')-phenazocine{{clarify|There are multiple stereocenters, so the two enantiomers cannot be distinguished as R and S|date=September 2022}} has twenty times the potency of [[morphine]] as an analgesic,<ref>{{cite journal | doi=10.1038/184451a0 | title=Identification of Phenazocine, a Potent New Analgesic | journal=Nature | date=August 1959 | volume=184 | issue=4684 | pages=451 | last1=Clarke | first1=E. G. C. | pmid=13810504 | bibcode=1959Natur.184..451C | s2cid=4190489 | doi-access=free }}</ref> while (''S'')-phenazocine has about four times the potency of morphine.<ref>Textbook of Pharmacology - Page 117</ref>{{full|date=September 2022}}

==History==

Phenazocine was invented in the 1950s.<ref name="Clarke">{{cite journal | author= Clarke EG | title=Identification of Phenazocine, a Potent New Analgesic | journal=Nature | date=August 8, 1959 | pages=451 | volume= 184 | issue= Suppl 7 | pmid=13810504 | doi= 10.1038/184451a0| bibcode=1959Natur.184..451C | s2cid=4190489 | doi-access=free }}</ref><ref name="Eckenhoff">{{cite journal | author= Eckenhoff JE | title=Phenazocine, a new benzomorphan narcotic analgesic | journal=Anesthesiology | date=May–June 1959 | pages=355–8 | volume=20 | issue=3 | pmid=13650222 | doi= 10.1097/00000542-195905000-00016| s2cid=30670011 }}</ref> It was one of a number of [[benzomorphan]] opioids (including [[pentazocine]], [[dezocine]], and [[cyclazocine]]) developed in the search for non-addictive strong analgesics.

Phenazocine was once widely used, and was mainly supplied as 5&nbsp;mg tablets of the [[hydrobromide]] salt for sublingual use (Narphen, Prinadol and other names), but its use was discontinued in the [[United Kingdom]] in 2001.<ref name="discontinueUK">{{cite web |date=February 2001 | url = http://www.connectingforhealth.nhs.uk/systemsandservices/data/readcodes/docs/tandc0201.pdf | archive-url = http://webarchive.nationalarchives.gov.uk/20081106082526/http://www.connectingforhealth.nhs.uk/systemsandservices/data/readcodes/docs/tandc0201.pdf | url-status = dead | archive-date = 2008-11-06 | title = Monthly Release Terming and Coding Newsletter | publisher = NHS Information Authority | access-date = 2008-01-11}} </ref>

Phenazocine was briefly used in the United States but fell out of favor;{{Citation needed|date=May 2013}} it remains a Schedule II substance under the Comprehensive Drug Abuse Control & Prevention Act (Controlled Substances Act) of 1970 (CSA) but is not manufactured. The DEA ACSCN for phenazocine is 9715 and its 2013 annual manufacturing quota was 6 grams.<ref>{{cite web | title = Quotas - 2013 | url = http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }}</ref>

==See also==

* [[Tapentadol]] - An opioid analgesic with reduced abuse-liability

==References==

{{Reflist|2}}

{{Analgesics}}

{{Hallucinogens}}

{{Opioidergics}}

[[Category:Benzomorphans]]

[[Category:Kappa-opioid receptor agonists]]

[[Category:Mu-opioid receptor agonists]]

[[Category:Phenols]]

[[Category:Synthetic opioids]]