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Onternabez

From Wikipedia, the free encyclopedia
Cannabidiol-derivative drug
Pharmaceutical compound
Onternabez
Clinical data
Other namesHU-308, HU308, PPP-003, ARDS-003
Drug classCB2 receptor agonist
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
ExcretionKidneys
Identifiers
  • [(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
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC27H42O3
Molar mass414.630 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
 ☒NcheckY (what is this?)  (verify)

Onternabez (also known asHU-308,HU308,PPP-003, andARDS-003) is asynthetic cannabinoid that acts as a potentcannabinoidagonist. It is highly selective for thecannabinoid-2 receptor (CB2 receptor) subtype, with a selectivity more than 5,000 times greater for the CB2 receptor than theCB1 receptor.[1][2][3] Thesynthesis and characterization of onternabez took place in the laboratory ofRaphael Mechoulam at theHebrew University of Jerusalem (the HU in HU-308) in the late 1990s. Thepinene dimethoxy-DMH-CBD derivative onternabez was identified as a potent peripheral CB2-selective agonist inin vitro and animal studies in 1990[1] and 1999.[2]

Legal status

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Onternabez is non-psychoactive and not scheduled at the federal level in the United States.[4] It is a Schedule Icontrolled substance in the state ofFlorida making it illegal to buy, sell, or possess there.[5]

See also

[edit]

References

[edit]
  1. ^abMechoulam 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.
  2. ^abHanus 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.
  4. ^"21 CFR — Schedules of controlled substances §1308.11 Schedule I." Archived fromthe original on 2009-08-27. Retrieved2014-12-17.
  5. ^"Chapter 893 - Drug abuse prevention and control".Florida Statutes.
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Retrieved from "https://en.wikipedia.org/w/index.php?title=Onternabez&oldid=1268772554"
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