Onternabez

Onternabez
Clinical data
Other names	HU-308, HU308, PPP-003, ARDS-003
Drug class	CB2 receptor agonist
ATC code	None;
Legal status
Legal status	CA: Schedule II; UK: Class B; US: Unscheduled ; ; Florida: Schedule I;
Pharmacokinetic data
Metabolism	Liver
Excretion	Kidneys
Identifiers
	IUPAC name [(1S,2S,5S)-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	11553430;
ChemSpider	8020425;
UNII	8I5L034D55;
KEGG	D12305;
ChEBI	CHEBI:146244;
CompTox Dashboard (EPA)	DTXSID801017327 ;
Chemical and physical data
Formula	C27H42O3
Molar mass	414.630 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC)[C@H]2C=C([C@@H]3C[C@H]2C3(C)C)CO)OC;
	InChI InChI=1S/C27H42O3/c1-8-9-10-11-12-26(2,3)19-14-23(29-6)25(24(15-19)30-7)20-13-18(17-28)21-16-22(20)27(21,4)5/h13-15,20-22,28H,8-12,16-17H2,1-7H3/t20-,21-,22+/m0/s1; Key:CFMRIVODIXTERW-FDFHNCONSA-N;
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Onternabez (also known as HU-308, HU308, PPP-003, and ARDS-003) is a synthetic cannabinoid that acts as a potent cannabinoid agonist. It is highly selective for the cannabinoid-2 receptor (CB₂ receptor) subtype, with a selectivity more than 5,000 times greater for the CB₂ receptor than the CB₁ receptor.^[1]^[2]^[3] The synthesis and characterization of onternabez took place in the laboratory of Raphael Mechoulam at the Hebrew University of Jerusalem (the HU in HU-308) in the late 1990s. The pinene dimethoxy-DMH-CBD derivative onternabez was identified as a potent peripheral CB₂-selective agonist in in vitro and animal studies in 1990^[1] and 1999.^[2]

^ ^a ^b Mechoulam R, Lander N, Breuer A, Zahalka J (1990-04-11). "Synthesis of the individual, pharmacologically distinct enantiomers of a tetrahydrocannabinol derivative". Tetrahedron Asymmetry. 1 (5): 315–318. doi:10.1016/S0957-4166(00)86322-3.
^ ^a ^b Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, et al. (December 1999). "HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor". Proceedings of the National Academy of Sciences of the United States of America. 96 (25): 14228–14233. Bibcode:1999PNAS...9614228H. doi:10.1073/pnas.96.25.14228. PMC 24419. PMID 10588688.
^ "Properties of HU-308 ~ Formula C27H42O3". Pitt Quantum Repository. University of Pittsburgh Department of Chemistry.

[Mechoulam_1990-1] Mechoulam R, Lander N, Breuer A, Zahalka J (1990-04-11). "Synthesis of the individual, pharmacologically distinct enantiomers of a tetrahydrocannabinol derivative". Tetrahedron Asymmetry. 1 (5): 315–318. doi:10.1016/S0957-4166(00)86322-3.

[Hanus_et_al_1999-2] Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, et al. (December 1999). "HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor". Proceedings of the National Academy of Sciences of the United States of America. 96 (25): 14228–14233. Bibcode:1999PNAS...9614228H. doi:10.1073/pnas.96.25.14228. PMC 24419. PMID 10588688.

[3] "Properties of HU-308 ~ Formula C27H42O3". Pitt Quantum Repository. University of Pittsburgh Department of Chemistry.

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