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{{Drugbox
{{Drugbox
| IUPAC_name = [(1R,2R,5R)-2-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]methanol
| IUPAC_name = [(1R,2R,5R)- 2-[2,6-dimethoxy- 4-(2-methyloctan- 2-yl) phenyl]- 7,7-dimethyl- 4-bicyclo [3.1.1] hept- 3-enyl] methanol
| image = HU-308.png
| image = HU-308.png
| width = 260
| width = 200
| CAS_number = 256934-39-1
| CAS_number = 256934-39-1
| ATC_prefix =
| ATC_prefix =
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==References==
==References==
{{reflist}}
<div class="references-small">
<references/>
</div>


{{Cannabinoids}}
{{Cannabinoids}}



Revision as of 14:57, 26 January 2009

Onternabez
Legal status
Legal status
  • In general: legal
Identifiers
  • [(1R,2R,5R)- 2-[2,6-dimethoxy- 4-(2-methyloctan- 2-yl) phenyl]- 7,7-dimethyl- 4-bicyclo [3.1.1] hept- 3-enyl] methanol
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H43O2
Molar mass414.621 g/mol g·mol−1
3D model (JSmol)
  • CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC)C2C=C(C3CC2C3(C)C)CO)OC

HU-308 is a drug which acts as a cannabinoid agonist. It is highly selective for the CB2 receptor subtype, with a selectivity of over 5000x for CB2 vs CB1.[1] The synthesis and characterization took place in the laboratory of Prof. Mechoulam at the Hebrew University of Jerusalem in the late 1990s. It has analgesic effects,[2] promotes proliferation of neural stem cells,[3] and protects both liver and blood vessel tissues against oxidative stress via inhibition of TNF-α.[4][5]

References

  1. ^ Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, Pertwee RG, Ross RA, Mechoulam R, Fride E. HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor. Proceedings of the National Academy of Sciences USA. 1999 Dec 7;96(25):14228-33. PMID 10588688
  2. ^ LaBuda CJ, Koblish M, Little PJ. Cannabinoid CB2 receptor agonist activity in the hindpaw incision model of postoperative pain. European Journal of Pharmacology. 2005 Dec 19;527(1-3):172-4. PMID 16316653
  3. ^ Palazuelos J, Aguado T, Egia A, Mechoulam R, Guzmán M, Galve-Roperh I. Non-psychoactive CB2 cannabinoid agonists stimulate neural progenitor proliferation. Federation of American Societies for Experimental Biology Journal. 2006 Nov;20(13):2405-7. PMID 17015409
  4. ^ Rajesh M, Pan H, Mukhopadhyay P, Bátkai S, Osei-Hyiaman D, Haskó G, Liaudet L, Gao B, Pacher P. Cannabinoid-2 receptor agonist HU-308 protects against hepatic ischemia/reperfusion injury by attenuating oxidative stress, inflammatory response, and apoptosis. Journal of Leukocyte Biology. 2007 Dec;82(6):1382-9. PMID 17652447
  5. ^ Rajesh M, Mukhopadhyay P, Bátkai S, Haskó G, Liaudet L, Huffman JW, Csiszar A, Ungvari Z, Mackie K, Chatterjee S, Pacher P. CB2-receptor stimulation attenuates TNF-alpha-induced human endothelial cell activation, transendothelial migration of monocytes, and monocyte-endothelial adhesion. American Journal of Physiology. Heart and Circulatory Physiology. 2007 Oct;293(4):H2210-8. PMID 17660390