imported>KarmaKangaroo: /* Recreational */ Naloxone information extraneous to the Pentazocine article, and whole paragraph describes Nalxone not the article drug. Naloxone has a high binding affinity for u receptors, but not the highest.

2025-11-01T13:24:09Z

Recreational: Naloxone information extraneous to the Pentazocine article, and whole paragraph describes Nalxone not the article drug. Naloxone has a high binding affinity for u receptors, but not the highest.

New page

{{Short description|Opioid medication}}
{{Drugbox
| Watchedfields = changed
| class = [[Opioid]]
| verifiedrevid = 464198314
| IUPAC_name = (2''RS'',6''RS'',11''RS'')-6,11-dimethyl-3-(3-methylbut-2-en-1-yl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol<br />or<br />2-dimethylallyl-5,9-dimethyl-2'-hydroxybenzomorphan
| image = Pentazocine-racemate2DCSD.svg
| image_class = skin-invert-image
| width = 350px
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RP4A60D26L
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VOKSWYLNZZRQPF-GDIGMMSISA-N
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 359-83-1
| ATC_prefix = N02
| ATC_suffix = AD01
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 560
| PubChem = 441278
| IUPHAR_ligand = 1606
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00652
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 390041
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00498
| C = 19
| H = 27
| N = 1
| O = 1
| SMILES = Oc1ccc3c(c1)[C@]2([C@H]([C@H](N(CC2)C\C=C(/C)C)C3)C)C
| bioavailability = ~20% orally
| metabolism = [[Liver|Hepatic]]
| onset = 15 min<ref>{{cite book | vauthors = Stitzel RE |title=Modern pharmacology with clinical applications |date=2004 |publisher=Lippincott Williams & Wilkins |location=Philadelphia |isbn=9780781737623 |page=325 |edition=6th |url= https://books.google.com/books?id=KqA29hQ-m3AC&pg=PA325 }}</ref>
| elimination_half-life = 2 to 3 hours
| duration_of_action =
| excretion = [[Kidney|Renal]]
| pregnancy_AU = C
| pregnancy_US = N
| pregnancy_US_comment =
| legal_AU = S8
| legal_BR = B1
| 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_DE = Anlage III
| legal_US = Schedule IV
| legal_UK = Class B
| legal_UN = P III
| routes_of_administration = [[By mouth]], [[intramuscular]], [[intravenous]]
| Drugs.com = {{drugs.com|monograph|pentazocine-hydrochloride}} (hydrochloride)<br />{{drugs.com|monograph|pentazocine-lactate}} (lactate)
}}

'''Pentazocine''',<ref>US Patent 4105659 Analgesia producing benzazocines</ref> sold under the brand name '''Talwin''' among others, is an [[analgesic]] medication used to treat moderate to severe [[pain]]. It is believed to work by activating (agonizing) [[kappa opioid receptor|κ-opioid receptors]] (KOR) and [[mu opioid receptor|μ-opioid receptors]] (MOR). As such it is called an [[opioid]] as it delivers its effects on pain by interacting with the opioid receptors. It shares many of the side effects of other opioids like [[constipation]], [[nausea]], [[Itch|itching]], [[drowsiness]], and [[respiratory depression]], but, unlike most other opioids, it fairly frequently causes [[hallucination]]s, [[nightmare]]s, and [[delusion]]s. It is also, unlike most other opioids, subject to a ceiling effect, which is when at a certain dose no more pain relief is obtained by increasing the dose any further.<ref name="mart"/>

Chemically it is classed as a [[benzomorphan]] and it comes in two [[enantiomers]], which are molecules that are exact (non-superimposable) mirror images of one another.


It was patented in 1960 and approved for medical use in 1964.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=527 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA527 |language=en}}</ref> Usually, in its oral formulations, it is combined with [[naloxone]] so as to prevent people from crushing the tablets, dissolving them in a solvent (like water) and injecting them for a high (as orally administered naloxone produces no opioid-negating effects as it has no oral bioavailability, whereas intravenous or intramuscular administration does).<ref name = mart/>

==Uses==

===Medical===
Pentazocine is used primarily to treat pain, although its analgesic effects are subject to a ceiling effect.<ref name="BNF">{{cite book | isbn = 978-0-85711-084-8 | title = British National Formulary (BNF) | last1 = Joint Formulary Committee | year = 2013 | publisher = Pharmaceutical Press | location = London, UK | edition = 65 | url-access = registration | url = https://archive.org/details/bnf65britishnati0000unse }}</ref> It has been discontinued by its corporate sponsor in [[Australia]], although it may be available through the special access scheme.<ref name = mart/>

===Recreational===
In the 1970s, recreational drug users discovered that combining pentazocine with [[tripelennamine]] (a first-generation ethylenediamine [[antihistamine]] most commonly dispensed under the brand names Pelamine and Pyribenzamine) produced a euphoric sensation. Since tripelennamine tablets are typically blue in color and brand-name Pentazocine is known as Talwin (hence "Ts"), the pentazocine/tripelennamine combination acquired the [[slang]] name ''Ts and blues''.<ref>{{cite journal | vauthors = Hudzik TJ, Slifer BL | title = The role of dopamine in the effects of pentazocine and tripelennamine | journal = Pharmacology, Biochemistry, and Behavior | volume = 36 | issue = 3 | pages = 547–554 | date = July 1990 | pmid = 1974066 | doi = 10.1016/0091-3057(90)90254-f | s2cid = 21976943 }}</ref><ref>{{cite journal | vauthors = Suzuki T, Masukawa Y, Shiozaki Y, Misawa M | title = Potentiation of pentazocine conditioned place preference by tripelennamine in rats | journal = Psychopharmacology | volume = 105 | issue = 1 | pages = 9–12 | year = 1991 | pmid = 1836064 | doi = 10.1007/BF02316857 | s2cid = 6288581 }}</ref><ref>{{cite journal | vauthors = Carter HS, Watson WA | title = IV pentazocine/methylphenidate abuse--the clinical toxicity of another Ts and blues combination | journal = Journal of Toxicology. Clinical Toxicology | volume = 32 | issue = 5 | pages = 541–547 | year = 1994 | pmid = 7932913 | doi = 10.3109/15563659409011058 }}</ref>
After health-care professionals and drug-enforcement officials became aware of this scenario, the [[mu opioid receptor|μ-opioid receptor]] antagonist [[naloxone]] was added to oral preparations containing pentazocine to prevent perceived "misuse" via injection,<ref name=monotabsnalox>{{ cite web | url = https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a28450a0-ac93-4235-b9a6-58cdf24773cb | title = Pentazocine and Naloxone tablets | work = DailyMed | publisher = National Institute of Health | access-date = 2011-12-10 }}</ref> and the reported incidence of its recreational use has declined precipitously since.

==Adverse effects==
[[Image:pentazocine.jpg|frame|right]]
Side effects are similar to those of [[morphine]], but due to pentazocine's action at the κ-opioid receptor, it is more likely to invoke [[psychotomimetic]] effects.<ref name = BNF/> High dose may cause [[hypertension|high blood pressure]] or [[tachycardia|high heart rate]].<ref name = mart>{{cite book | chapter = Pentazocine | title = Martindale: The Complete Drug Reference |publisher=Pharmaceutical Press|place=London, UK|date=9 January 2017|access-date=1 September 2017|url=http://www.medicinescomplete.com/mc/martindale/current/ms-6251-l.htm| veditors = Brayfield A }}</ref> It may also increase cardiac work after [[myocardial infarction]] when given intravenously and hence this use should be avoided where possible.<ref name = mart/> [[Respiratory depression]] is a common side effect, but is subject to a ceiling effect, such that at a certain dose the degree of respiratory depression will no longer increase with dose increases.<ref name = mart/> Albeit rarely, pentazocine has been associated with [[agranulocytosis]], [[erythema multiforme]] and [[toxic epidermal necrolysis]].<ref name = mart/>

===Tissue damage at injection sites===
Severe injection site necrosis and sepsis has occurred (sometimes requiring amputation of limb) with multiple injection of pentazocine lactate. In addition, animal studies have demonstrated that Pentazocine is tolerated less well subcutaneously than intramuscularly.<ref name=mono>{{ cite web | url = https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=1d225639-c326-4d9e-bc8d-e380e7958b8f | title = TALWIN (pentazocine lactate) injection, solution | work = DailyMed | publisher = National Institute of Health | access-date = 2011-12-10 }}</ref>

==History==
Pentazocine was developed by the [[Sterling Drug]] Company, Sterling-Winthrop Research Institute, of [[Rensselaer, New York]]. The [[analgesic]] compound was first made at Sterling in 1958. U.S. testing was conducted between 1961 and 1967. It was approved by the [[Food and Drug Administration]] in June 1967 after being favorably reviewed following testing on 12,000 patients in the [[United States]]. By mid 1967 Pentazocine was already being sold in [[Mexico]], [[England]], and [[Argentina]], under different trade names.<ref name=talwin>''Pain-Killing Drug Approved By F.D.A.'', [[New York Times]], June 27, 1967, pg. 41.</ref>

==Society and culture==

=== Legal status ===

==== United States ====
Pentazocine was originally unclassified under the [[Controlled Substances Act]] in the United States. A petition was filed with the US [[Drug Enforcement Administration]] (DEA) on October 1, 1971, to shift it to Schedule III. The petition was filed by Joseph L. Fink III, a pharmacist and law student at Georgetown University Law Center as part of the course Lawyering in the Public Interest. That petition was accepted for review on November 10, 1971.<ref>{{Cite book|url=https://books.google.com/books?id=KwxbE1NioK0C&q=Fed.Reg.%20217%20pentazocine&pg=PA21527|title=36 Fed.Reg. 217|date=November 1971}}</ref> The DEA published a Final Rule transferring it to Schedule IV on January 10, 1979, with an effective date of February 9, 1979.<ref>{{Cite book|url=https://books.google.com/books?id=Cwne3Vsh-AIC&q=44%20Fed.%20Reg.%202169%20pentazocine&pg=PA2169|title=44 Fed. Reg. 2169|year=1979}}</ref> Pentazocine is still classified in [[Controlled Substances Act#Schedule IV controlled substances|Schedule IV]] under the Controlled Substances Act in the United States, even with the addition of naloxone. Some states classify it in Schedule II, such as Illinois<ref>{{Cite web|url=http://www.ilga.gov/legislation/ilcs/ilcs4.asp?DocName=072005700HArt%2E+II&ActID=1941&ChapterID=53&SeqStart=600000&SeqEnd=2600000|title=Illinois Controlled Substances Act|website=Illinois General Assembly}}</ref> and South Carolina (injectable form only),<ref>{{Cite web|url=http://www.scdhec.gov/Health/FHPF/DrugControlRegisterVerify/ControlledSubstanceSchedule/|title=South Carolina DHEC Controlled Substance Schedule|website=South Carolina Department of Health and Environmental Control|access-date=2018-05-04|archive-date=2018-09-01|archive-url=https://web.archive.org/web/20180901193544/http://www.scdhec.gov/Health/FHPF/DrugControlRegisterVerify/ControlledSubstanceSchedule/|url-status=dead}}</ref> or Schedule III such as Kentucky.<ref>{{Cite web|url=http://www.chfs.ky.gov/NR/rdonlyres/D9B4E4D4-54C6-4439-9AA1-2B70BE4DF188/0/KentuckyScheduledDrugList11262014.pdf|title=Kentucky Scheduled Drug List|website=Kentucky Cabinet for Health and Family Services|access-date=2018-05-04|archive-date=2017-01-31|archive-url=https://web.archive.org/web/20170131180738/http://chfs.ky.gov/NR/rdonlyres/D9B4E4D4-54C6-4439-9AA1-2B70BE4DF188/0/KentuckyScheduledDrugList11262014.pdf|url-status=dead}}</ref>) Internationally, pentazocine is a Schedule III drug under the [[Convention on Psychotropic Substances]],<ref>{{cite web | url = http://www.incb.org/documents/Psychotropics/greenlist/2016/V1604744_Eng.pdf | title = List of psychotropic substances under international control | work = Green List - Annex to the annual statistical report on psychotropic substances (form P) | edition = 27th | date = 2016 | publisher = International Narcotics Control Board | access-date = 2017-10-02 | archive-date = 2017-04-21 | archive-url = https://web.archive.org/web/20170421003842/https://www.incb.org/documents/Psychotropics/greenlist/2016/V1604744_Eng.pdf | url-status = dead }}</ref> except in Canada where it is Schedule I under the federal [[Controlled Drugs and Substances Act]]. Pentazocine has a DEA ACSCN of 9720; being a Schedule IV substance, the DEA does not assign an annual manufacturing quota for pentazocine for the United States.

===Brand names===
Pentazocine is sold under several brand names, such as Fortral, Sosegon, Talwin NX (with naloxone), Talwin, Talwin PX, Fortwin, and Talacen (with [[paracetamol]] [acetaminophen]).

== Research ==
In one clinical study, pentazocine was found to rapidly and substantially reduce symptoms of [[mania]] in individuals with [[bipolar disorder]] that were in the manic phase of the condition.<ref name="ChartoffMavrikaki2015">{{cite journal |vauthors=Chartoff EH, Mavrikaki M |year=2015 |title=Sex Differences in Kappa Opioid Receptor Function and Their Potential Impact on Addiction |journal=Frontiers in Neuroscience |volume=9 |pages=466 |doi=10.3389/fnins.2015.00466 |pmc=4679873 |pmid=26733781 |doi-access=free}}</ref> It was postulated that the efficacy observed was due to [[κ-opioid receptor]] activation-mediated amelioration of [[dopamine|hyperdopaminergia]] in the [[reward pathway]]s.<ref name="ChartoffMavrikaki2015" /> Minimal [[sedation]] and no [[side effect]]s including [[psychotomimetic]] effects or worsening of [[psychosis]] were observed at the dose administered.<ref name="ChartoffMavrikaki2015" />

== See also ==
* [[Cyclazocine]]
* [[Volazocine]]

== References ==
{{reflist}}

== External links ==
* [http://www.eurekalert.org/pub_releases/2003-03/mu-rwr032403.php Eurekalert report on PNAS article] {{Webarchive|url=https://web.archive.org/web/20210214010259/https://www.eurekalert.org/pub_releases/2003-03/mu-rwr032403.php |date=2021-02-14 }}

{{Analgesics}}
{{Hallucinogens}}
{{Opioid receptor modulators}}
{{Sigma receptor modulators}}

[[Category:Alkene derivatives]]
[[Category:Benzomorphans]]
[[Category:Kappa-opioid receptor agonists]]
[[Category:Hydroxyarenes]]
[[Category:Hallucinogens]]
[[Category:Sigma agonists]]
[[Category:Synthetic opioids]]

Pentazocine - Revision history

imported>KarmaKangaroo: /* Recreational */ Naloxone information extraneous to the Pentazocine article, and whole paragraph describes Nalxone not the article drug. Naloxone has a high binding affinity for u receptors, but not the highest.