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Cannabidiol-derivative drug
Onternabez
Legal status
Metabolism
Liver
Excretion Kidneys
[(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
PubChem
CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (
EPA )
Formula C 27 H 42 O 3
Molar mass 414.630 g·mol−1 3D model (
JSmol )
CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC)[C@H]2C=C([C@@H]3C[C@H]2C3(C)C)CO)OC
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]
Legal status
Onternabez is non-psychoactive and not scheduled at the federal level in the United States.
[4] It is a Schedule I
controlled substance in the state of
Florida making it illegal to buy, sell, or possess there.
[5]
See also
References
^
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.
^
"21 CFR — Schedules of controlled substances §1308.11 Schedule I." Archived from
the original on 2009-08-27. Retrieved 2014-12-17 .
^
"Chapter 893 - Drug abuse prevention and control" . Florida Statutes .
Phytocannabinoids (
comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
Eicosanoids
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)