PB-22

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Chemical compound

title: "PB-22" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["cannabinoids", "designer-drugs", "indoles"] description: "Chemical compound" topic_path: "general/cannabinoids" source: "https://en.wikipedia.org/wiki/PB-22" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = | verifiedrevid = | IUPAC_name = 1-Pentyl-1H-indole-3-carboxylic acid 8-quinolinyl ester | image = PB-22.png | image_class = skin-invert-image | width = 200

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = Schedule II | legal_UK = Class B | legal_US = Schedule I | legal_DE = Anlage II | routes_of_administration =

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

| CAS_number_Ref = | CAS_number = 1400742-17-7 | ATC_prefix = | ATC_suffix = | PubChem = 71604304 | DrugBank_Ref = | DrugBank = | UNII_Ref = | 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

| C=23 | H=22 | N=2 | O=2

PB-22 (QUPIC, SGT-21 or 1-pentyl-1H-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. 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 EC50 of 5.1 nM for human CB1 receptors, and 37 nM for human CB2 receptors. PB-22 produces bradycardia and hypothermia in rats at doses of 0.3–3 mg/kg, suggesting potent cannabinoid-like activity. 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. One clinical toxicology study found PB-22 to be the cause of seizures in a human and his dog.

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. 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.

Legal status

As of 9 May 2014, PB-22 is no longer legal in New Zealand.

In January 2014, PB-22 was designated as a Schedule I controlled substance in the United States.

In Ohio, PB-22 is illegal.

Florida also has banned PB-22.

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.

References

References

  1. (2013). "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". Forensic Toxicology.
  2. (July 2021). "Pharmacokinetic Approach to Combat the Synthetic Cannabinoid PB-22". ACS Chemical Neuroscience.
  3. (August 2015). "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". ACS Chemical Neuroscience.
  4. (July 2014). "'Crazy Monkey' poisons man and dog: Human and canine seizures due to PB-22, a novel synthetic cannabinoid". Clinical Toxicology.
  5. (January 2021). "Synthetic cannabinoid receptor agonists: Analytical profiles and development of QMPSB, QMMSB, QMPCB, 2F-QMPSB, QMiPSB, and SGT-233". Drug Testing and Analysis.
  6. [http://forendex.southernforensic.org/index.php/detail/index/1232 Forendex entry], Southern Association of Forensic Scientists
  7. (1 May 2014). "Legal highs pulled from shelves". New Zealand Media and Entertainment.
  8. (October 2014). "Four postmortem case reports with quantitative detection of the synthetic cannabinoid, 5F-PB-22". Journal of Analytical Toxicology.
  9. "PB-22 and 5F-PB-22". [[Drug Enforcement Administration]], Office of Diversion Control.
  10. Pelzer, Jeremy. (April 17, 2014). "Ohio bans two synthetic marijuana drugs sold as "herbal incense"". cleveland.com.
  11. (1997-05-06). "Statutes & Constitution :View Statutes : Online Sunshine". Leg.state.fl.us.
  12. (27 September 2015). "关于印发《非药用类麻醉药品和精神药品列管办法》的通知". China Food and Drug Administration.

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cannabinoidsdesigner-drugsindoles