PB-22

PB-22
Legal status
Legal status
Identifiers
  • 1-Pentyl-1H-indole-3-carboxylic acid 8-quinolinyl ester
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.233.114 Edit this at Wikidata
Chemical and physical data
FormulaC23H22N2O2
Molar mass358.441 g·mol−1
3D model (JSmol)
  • CCCCCN1C=C(C2=CC=CC=C21)C(=O)OC3=CC=CC4=C3N=CC=C4
  • InChI=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
  • Key:ZAVGICCEAOUWFM-UHFFFAOYSA-N

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.[1][2] 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.[3] PB-22 produces bradycardia and hypothermia in rats at doses of 0.3–3 mg/kg, suggesting potent cannabinoid-like activity.[3] 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.[3] One clinical toxicology study found PB-22 to be the cause of seizures in a human and his dog.[4]

  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. S2CID 1279637.
  2. ^ Lin M, Ellis B, Eubanks LM, Janda KD (July 2021). "Pharmacokinetic Approach to Combat the Synthetic Cannabinoid PB-22". ACS Chemical Neuroscience. 12 (14): 2573–2579. doi:10.1021/acschemneuro.1c00360. PMID 34254505. S2CID 235808519.
  3. ^ a b c 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): 1445–1458. doi:10.1021/acschemneuro.5b00107. PMID 25921407.
  4. ^ 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): 635–638. doi:10.3109/15563650.2014.925562. PMID 24905571. S2CID 207647659.