{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = | verifiedrevid = | IUPAC_name = 1-Pentyl-1''H''-indole-3-carboxylic acid 8-quinolinyl ester | image = PB-22 structure.svg | image_class = skin-invert-image | width = 200

<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = Schedule II | legal_UK = Class B | legal_US = Schedule I | legal_DE = Anlage II | routes_of_administration =

<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

<!--Identifiers--> | CAS_number_Ref = | CAS_number = 1400742-17-7 | ATC_prefix = | ATC_suffix = | PubChem = 71604304 | DrugBank_Ref = | DrugBank = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = QM6J8F29FE | ChemSpiderID = 29339966 | smiles = CCCCCN1C=C(C2=CC=CC=C21)C(=O)OC3=CC=CC4=C3N=CC=C4 | StdInChI = 1S/C23H22N2O2/c1-2-3-6-15-25-16-19(18-11-4-5-12-20(18)25)23(26)27-21-13-7-9-17-10-8-14-24-22(17)21/h4-5,7-14,16H,2-3,6,15H2,1H3 | StdInChIKey = ZAVGICCEAOUWFM-UHFFFAOYSA-N

<!--Chemical data--> | C=23 | H=22 | N=2 | O=2 }}

'''PB-22''' ('''QUPIC''', '''SGT-21''' or '''1-pentyl-1''H''-indole-3-carboxylic acid 8-quinolinyl ester''') is a designer drug offered by online vendors as a cannabimimetic agent, and detected being sold in synthetic cannabis products in Japan in 2013.<ref>{{cite journal | vauthors = Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y | title = Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products | doi = 10.1007/s11419-013-0182-9 | journal = Forensic Toxicology | year = 2013 | volume=31 | issue = 2 | pages=223–240| s2cid = 1279637 }}</ref><ref>{{cite journal | vauthors = Lin M, Ellis B, Eubanks LM, Janda KD | title = Pharmacokinetic Approach to Combat the Synthetic Cannabinoid PB-22 | journal = ACS Chemical Neuroscience | volume = 12 | issue = 14 | pages = 2573–2579 | date = July 2021 | pmid = 34254505 | doi = 10.1021/acschemneuro.1c00360 | s2cid = 235808519 }}</ref> PB-22 represents a structurally unique synthetic cannabinoid chemotype, since it contains an ester linker at the indole 3-position, rather than the precedented ketone of JWH-018 and its analogs, or the amide of APICA and its analogs.

PB-22 has an EC<sub>50</sub> of 5.1&nbsp;nM for human CB<sub>1</sub> receptors, and 37&nbsp;nM for human CB<sub>2</sub> receptors.<ref name="ACS 2015">{{cite journal | vauthors = Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M | display-authors = 6 | title = Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135 | journal = ACS Chemical Neuroscience | volume = 6 | issue = 8 | pages = 1445–1458 | date = August 2015 | pmid = 25921407 | doi = 10.1021/acschemneuro.5b00107 | url = https://zenodo.org/record/47750 }}</ref> PB-22 produces bradycardia and hypothermia in rats at doses of 0.3–3&nbsp;mg/kg, suggesting potent cannabinoid-like activity.<ref name="ACS 2015" /> The magnitude and duration of hypothermia induced in rats by PB-22 was notably greater than JWH-018, AM-2201, UR-144, XLR-11, APICA, or STS-135, with a reduction of body temperature still observable six hours after dosing.<ref name="ACS 2015" /> One clinical toxicology study found PB-22 to be the cause of seizures in a human and his dog.<ref>{{cite journal | vauthors = Gugelmann H, Gerona R, Li C, Tsutaoka B, Olson KR, Lung D | title = 'Crazy Monkey' poisons man and dog: Human and canine seizures due to PB-22, a novel synthetic cannabinoid | journal = Clinical Toxicology | volume = 52 | issue = 6 | pages = 635–638 | date = July 2014 | pmid = 24905571 | doi = 10.3109/15563650.2014.925562 | s2cid = 207647659 }}</ref>

==History== PB-22 was originally developed by New Zealand legal highs company Stargate International in 2012 as SGT-21, intended to be a structural hybrid of QMPSB and JWH-018.<ref>{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, Bowden MJ, Williamson JP | title = Synthetic cannabinoid receptor agonists: Analytical profiles and development of QMPSB, QMMSB, QMPCB, 2F-QMPSB, QMiPSB, and SGT-233 | journal = Drug Testing and Analysis | volume = 13 | issue = 1 | pages = 175–196 | date = January 2021 | pmid = 32880103 | doi = 10.1002/dta.2913 | doi-access = free }}</ref> However, no intellectual property protection was applied for and the compound quickly became subject to widespread grey-market sales outside the control of the inventors.

== Detection == A forensic standard of PB-22 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.<ref>[http://forendex.southernforensic.org/index.php/detail/index/1232 Forendex entry], Southern Association of Forensic Scientists</ref>

== Legal status == As of 9 May 2014, PB-22 is no longer legal in New Zealand.<ref>{{cite web|url=http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=11247774|title=Legal highs pulled from shelves|work=New Zealand Herald | vauthors = Jones N |date=1 May 2014 |publisher = New Zealand Media and Entertainment |access-date=18 August 2020 }}</ref>

In January 2014, PB-22 was designated as a Schedule I controlled substance in the United States.<ref name=pmid24876364>{{cite journal | vauthors = Behonick G, Shanks KG, Firchau DJ, Mathur G, Lynch CF, Nashelsky M, Jaskierny DJ, Meroueh C | display-authors = 6 | title = Four postmortem case reports with quantitative detection of the synthetic cannabinoid, 5F-PB-22 | journal = Journal of Analytical Toxicology | volume = 38 | issue = 8 | pages = 559–562 | date = October 2014 | pmid = 24876364 | pmc = 4334789 | doi = 10.1093/jat/bku048 }}</ref><ref>{{cite web | url= http://www.deadiversion.usdoj.gov/drug_chem_info/spice/pb22.pdf | title= PB-22 and 5F-PB-22 | publisher= Drug Enforcement Administration, Office of Diversion Control | access-date= 2014-05-21 | archive-date= 2024-05-21 | archive-url= https://web.archive.org/web/20240521111109/https://www.deadiversion.usdoj.gov/drug_chem_info/spice/pb22.pdf | url-status= dead }}</ref>

In Ohio, PB-22 is illegal.<ref>{{Cite news | url = http://www.cleveland.com/open/index.ssf/2014/04/ohio_bans_two_synthetic_mariju.html | title = Ohio bans two synthetic marijuana drugs sold as "herbal incense" | first = Jeremy | last = Pelzer | name-list-style = vanc | date = April 17, 2014 | publisher = cleveland.com}}</ref>

Florida also has banned PB-22.<ref>{{cite web|url=http://www.leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&Search_String=&URL=0800-0899/0893/Sections/0893.03.html |title=Statutes & Constitution :View Statutes : Online Sunshine |publisher=Leg.state.fl.us |date=1997-05-06 |access-date=2014-07-12}}</ref>

Since 13 December 2014 it is also illegal in Germany because of adding the substance to the BtMG Anlage II.

As of October 2015 PB-22 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

== See also == * 5F-PB-22 * QUCHIC * APICA

== References == {{reflist}}

{{Cannabinoids}}

Category:Cannabinoids Category:Designer drugs Category:Indoles