PB-22

PB-22 (QUPIC 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.[1] The structure of PB-22 appears to use an understanding of structure-activity relationships within the indole class of cannabimimetics, although its design origins are unclear. 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
Legal status
Legal status
Identifiers
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.233.114
Chemical and physical data
FormulaC23H22N2O2
Molar mass358.441 g·mol−1
3D model (JSmol)

PB-22 has an EC50 of 5.1 nM for human CB1 receptors, and 37 nM for human CB2 receptors.[2] PB-22 produces bradycardia and hypothermia in rats at doses of 0.3–3 mg/kg, suggesting potent cannabinoid-like activity.[2] 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.[2] One clinical toxicology study found PB-22 to be the cause of seizures in a human and his dog.[3]

Detection

A forensic standard of PB-22 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[4]

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.[5][6]

In Ohio, PB-22 is illegal.[7]

Florida also has banned PB-22.[8]

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.[9]

See also

References
  1. Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (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. 31 (2): 223–240. doi:10.1007/s11419-013-0182-9.
  2. Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, et al. (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. 6 (8): 1445–58. doi:10.1021/acschemneuro.5b00107. PMID 25921407.
  3. Gugelmann H, Gerona R, Li C, Tsutaoka B, Olson KR, Lung D (July 2014). "'Crazy Monkey' poisons man and dog: Human and canine seizures due to PB-22, a novel synthetic cannabinoid". Clinical Toxicology. 52 (6): 635–8. doi:10.3109/15563650.2014.925562. PMID 24905571.
  4. Forendex entry, Southern Association of Forensic Scientists
  5. Behonick G, Shanks KG, Firchau DJ, Mathur G, Lynch CF, Nashelsky M, et al. (October 2014). "Four postmortem case reports with quantitative detection of the synthetic cannabinoid, 5F-PB-22". Journal of Analytical Toxicology. 38 (8): 559–62. doi:10.1093/jat/bku048. PMC 4334789. PMID 24876364.
  6. "PB-22 and 5F-PB-22" (PDF). Drug Enforcement Administration, Office of Diversion Control.
  7. Jeremy Pelzer (April 17, 2014). "Ohio bans two synthetic marijuana drugs sold as "herbal incense"". cleveland.com.
  8. "Statutes & Constitution :View Statutes : Online Sunshine". Leg.state.fl.us. 1997-05-06. Retrieved 2014-07-12.
  9. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
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