HU-308

HU-308
	File:HU-308.png
Legal status
Legal status	In general: legal;
Identifiers
	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;
CAS Number	256934-39-1;
PubChem CID	5311172;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C27H43O2
Molar mass	414.621 g/mol
3D model (JSmol)	Interactive image;
	SMILES 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] 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]

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References[edit | edit source]

↑ 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
↑ 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
↑ 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
↑ 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
↑ 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

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[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

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Legal status
File:HU-308.png
Legal status	In general: legal
Identifiers
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
CAS Number	256934-39-1
PubChem CID	5311172
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₇H₄₃O₂
Molar mass	414.621 g/mol
3D model (JSmol)	Interactive image
SMILES CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC)C2C=C(C3CC2C3(C)C)CO)OC