PB-22

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PB-22
PB-22.png
Systematic (IUPAC) name
1-Pentyl-1H-indole-3-carboxylic acid 8-quinolinyl ester
Legal status
Legal status
Identifiers
CAS Number 1400742-17-7
ChemSpider 29339966
Chemical data
Formula C23H22N2O2
Molar mass 358.43 g/mol

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,[original research?] 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 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[edit]

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

Legal status[edit]

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

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[edit]

References[edit]

  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. ^ a b c Banister, S. D.; Stuart, J.; Kevin, R. C.; Edington, A.; Longworth, M.; Wilkinson, S. M.; Beinat, C.; Buchanan, A. S.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (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): 150508124201002. doi:10.1021/acschemneuro.5b00107. 
  3. ^ Gugelmann, H.; Gerona, R.; Li, C.; Tsutaoka, B.; Olson, K. R.; Lung, D. (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, K. G.; Firchau, D. J.; Mathur, G; Lynch, C. F.; Nashelsky, M; Jaskierny, D. J.; Meroueh, C (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 4334789free to read. 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. Retrieved 1 October 2015.