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	CA: Schedule II
Identifiers
IUPAC name Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone
CAS Number	432047-72-8
PubChem CID	9799417
ChemSpider	7975182
UNII	9XRJ6055XT
ChEMBL	ChEMBL244403
CompTox Dashboard (EPA)	DTXSID60430920
Chemical and physical data
Formula	C26H24O2
Molar mass	368.476 g·mol^−1
3D model (JSmol)	Interactive image
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
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Legal Status

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

See also

• AM-6545
• AZ-11713908

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.