Onternabez

Last updated
Onternabez
Onternabez.svg
Clinical data
Other namesHU-308, HU308, PPP-003, ARDS-003
Drug class CB2 receptor agonist
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver
Excretion Kidneys
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
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
Formula C27H42O3
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
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

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

  1. 1 2 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 .
  2. 1 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. Archived from the original on 2022-08-17. Retrieved 2021-02-18.
  4. ↑ "21 CFR — Schedules of controlled substances §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  5. ↑ "Chapter 893 - Drug abuse prevention and control". Florida Statutes.
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