Jump to content

Onternabez

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Materialscientist (talk | contribs) at 12:06, 1 May 2020 (Reverted edits by 212.8.63.3 (talk) to last version by OAbot). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Onternabez
Legal status
Legal status
Identifiers
  • [(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
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H43O3
Molar mass415.638 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)

HU-308 is a drug that 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] The synthesis and characterization took place in the laboratory of Prof. Mechoulam at the Hebrew University of Jerusalem in the late 1990s. It has analgesic effects,[2] immunomodulatory properties in vitro,[3] promotes proliferation of neural stem cells,[4] and protects both liver and blood vessel tissues against oxidative stress via inhibition of TNF-α.[5][6]

United States

HU-308 is not scheduled at the federal level in the United States.[7]

Florida

"HU-308 ([(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)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[8]

See also

References

  1. ^ 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): 14228–33. Bibcode:1999PNAS...9614228H. doi:10.1073/pnas.96.25.14228. PMC 24419. PMID 10588688.
  2. ^ LaBuda CJ, Koblish M, Little PJ (December 2005). "Cannabinoid CB2 receptor agonist activity in the hindpaw incision model of postoperative pain". European Journal of Pharmacology. 527 (1–3): 172–4. doi:10.1016/j.ejphar.2005.10.020. PMID 16316653.
  3. ^ Saroz Y, Kho DT, Glass M, Graham ES, Grimsey NL (2019-10-19). "Cannabinoid Receptor 2 (CB 2 ) Signals via G-alpha-s and Induces IL-6 and IL-10 Cytokine Secretion in Human Primary Leukocytes". ACS Pharmacology & Translational Science. 2 (6): 414–428. doi:10.1021/acsptsci.9b00049. ISSN 2575-9108.
  4. ^ Palazuelos J, Aguado T, Egia A, Mechoulam R, Guzmán M, Galve-Roperh I (November 2006). "Non-psychoactive CB2 cannabinoid agonists stimulate neural progenitor proliferation". FASEB Journal. 20 (13): 2405–7. doi:10.1096/fj.06-6164fje. PMID 17015409.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  5. ^ Rajesh M, Pan H, Mukhopadhyay P, Bátkai S, Osei-Hyiaman D, Haskó G, et al. (December 2007). "Cannabinoid-2 receptor agonist HU-308 protects against hepatic ischemia/reperfusion injury by attenuating oxidative stress, inflammatory response, and apoptosis". Journal of Leukocyte Biology. 82 (6): 1382–9. doi:10.1189/jlb.0307180. PMC 2225476. PMID 17652447.
  6. ^ Rajesh M, Mukhopadhyay P, Bátkai S, Haskó G, Liaudet L, Huffman JW, et al. (October 2007). "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. 293 (4): H2210-8. doi:10.1152/ajpheart.00688.2007. PMC 2229632. PMID 17660390.
  7. ^ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
  8. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
Retrieved from "https://en.wikipedia.org/w/index.php?title=Onternabez&oldid=954245459"