PB-22

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

Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I
Identifiers
IUPAC name 1-Pentyl-1H-indole-3-carboxylic acid 8-quinolinyl ester
CAS Number	1400742-17-7
ChemSpider	29339966
UNII	QM6J8F29FE
CompTox Dashboard (EPA)	DTXSID70856177
ECHA InfoCard	100.233.114
Chemical and physical data
Formula	C23H22N2O2
Molar mass	358.441 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCN1C=C(C2=CC=CC=C21)C(=O)OC3=CC=CC4=C3N=CC=C4
InChI 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 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]

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.^[5] 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.^[6]

Legal status

As of 9 May 2014, PB-22 is no longer legal in New Zealand.^[7]

In January 2014, PB-22 was designated as a Schedule I controlled substance in the United States.^[8][9]

In Ohio, PB-22 is illegal.^[10]

Florida also has banned PB-22.^[11]

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.^[12]

See also

• 5F-PB-22
• QUCHIC
• APICA

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. 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. 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.
5. Brandt SD, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, Bowden MJ, Williamson JP (January 2021). "Synthetic cannabinoid receptor agonists: Analytical profiles and development of QMPSB, QMMSB, QMPCB, 2F-QMPSB, QMiPSB, and SGT-233". Drug Testing and Analysis. 13 (1): 175–196. doi:10.1002/dta.2913. PMID 32880103.
6. Forendex entry, Southern Association of Forensic Scientists
7. Jones N (1 May 2014). "Legal highs pulled from shelves". New Zealand Herald. New Zealand Media and Entertainment. Retrieved 18 August 2020.
8. 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): 559–562. doi:10.1093/jat/bku048. PMC 4334789. PMID 24876364.
9. "PB-22 and 5F-PB-22" (PDF). Drug Enforcement Administration, Office of Diversion Control.
10. Pelzer J (April 17, 2014). "Ohio bans two synthetic marijuana drugs sold as "herbal incense"". cleveland.com.
11. "Statutes & Constitution :View Statutes : Online Sunshine". Leg.state.fl.us. 1997-05-06. Retrieved 2014-07-12.
12. "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.