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
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. 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.