CB-13

CB-13 (CRA13, SAB-378)[1] is a cannabinoid drug, which acts as a potent agonist at both the CB1 and CB2 receptors, but has poor blood–brain barrier penetration, and so produces only peripheral effects at low doses, with symptoms of central effects such as catalepsy only appearing at much higher dose ranges. It has antihyperalgesic properties in animal studies,[2] and has progressed to preliminary human trials.[3]

CB-13
Legal status
Legal status
Identifiers
IUPAC name
  • Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H24O2
Molar mass368.476 g·mol−1
3D model (JSmol)
SMILES
  • c13ccccc1cccc3C(=O)c4ccc(OCCCCC)c2ccccc24
InChI
  • InChI=1S/C26H24O2/c1-2-3-8-18-28-25-17-16-24(21-13-6-7-14-22(21)25)26(27)23-15-9-11-19-10-4-5-12-20(19)23/h4-7,9-17H,2-3,8,18H2,1H3
  • Key:RSUMDJRTAFBISX-UHFFFAOYSA-N
  (verify)

As of October 2015 CB-13 is a controlled substance in China.[4]

See also

References
  1. Cluny, N. L.; Keenan, C. M.; Duncan, M.; Fox, A.; Lutz, B.; Sharkey, K. A. (2010). "Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone (SAB378), a Peripherally Restricted Cannabinoid CB1/CB2 Receptor Agonist, Inhibits Gastrointestinal Motility but Has No Effect on Experimental Colitis in Mice". Journal of Pharmacology and Experimental Therapeutics. 334 (3): 973–80. doi:10.1124/jpet.110.169946. PMID 20571060. S2CID 9198992.
  2. Dziadulewicz, E. K.; Bevan, S. J.; Brain, C. T.; Coote, P. R.; Culshaw, A. J.; Davis, A. J.; Edwards, L. J.; Fisher, A. J.; Fox, A. J.; Gentry, C.; Groarke, A.; Hart, T. W.; Huber, W.; James, I. F.; Kesingland, A.; La Vecchia, L.; Loong, Y.; Lyothier, I.; McNair, K.; O'Farrell, C.; Peacock, M.; Portmann, R.; Schopfer, U.; Yaqoob, M.; Zadrobilek, J. (2007). "Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: A Potent, Orally Bioavailable Human CB1/CB2Dual Agonist with Antihyperalgesic Properties and Restricted Central Nervous System Penetration". Journal of Medicinal Chemistry. 50 (16): 3851–3856. doi:10.1021/jm070317a. PMID 17630726.
  3. Gardin A, Kucher K, Kiese B, Appel-Dingemanse S (April 2009). "Cannabinoid receptor agonist 13, a novel cannabinoid agonist: first in human pharmacokinetics and safety". Drug Metabolism and Disposition. 37 (4): 827–33. doi:10.1124/dmd.108.024000. PMID 19144772. S2CID 15150118.
  4. "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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