O-1812

O-1812
O-1812
Systematic (IUPAC) name
(5Z,8Z,11Z,14Z)-20-cyano-N-[(2R)-1-hydroxypropan-2-yl]-16,16-dimethylicosa-5,8,11,14-tetraenamide
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
ATC code  ?
PubChem CID 9823107
Chemical data
Formula C26H42N2O2 
Mol. mass 414.622 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

O-1812 is an eicosanoid derivative related to anandamide, which acts as a potent and highly selective agonist for the cannabinoid receptor CB1, with a Ki of 3.4nM at CB1 and 3870nM at CB2.[1] Unlike most related compounds, O-1812 is metabolically stable against rapid breakdown by enzymes, and produces a cannabinoid-like discriminative effect in rats, which is similar but not identical to that produced by cannabinoid drugs of other chemical classes.[2][3][4][5]

See also


References

  1. ^ Di Marzo V, Bisogno T, De Petrocellis L, Brandi I, Jefferson RG, Winckler RL, Davis JB, Dasse O, Mahadevan A, Razdan RK, Martin BR (February 2001). "Highly selective CB(1) cannabinoid receptor ligands and novel CB(1)/VR(1) vanilloid receptor "hybrid" ligands". Biochemical and Biophysical Research Communications 281 (2): 444–51. doi:10.1006/bbrc.2001.4354. PMID 11181068. 
  2. ^ Baskfield CY, Martin BR, Wiley JL (April 2004). "Differential effects of delta9-tetrahydrocannabinol and methanandamide in CB1 knockout and wild-type mice". The Journal of Pharmacology and Experimental Therapeutics 309 (1): 86–91. doi:10.1124/jpet.103.055376. PMID 14718593. 
  3. ^ Wiley JL, LaVecchia KL, Karp NE, Kulasegram S, Mahadevan A, Razdan RK, Martin BR (August 2004). "A comparison of the discriminative stimulus effects of delta(9)-tetrahydrocannabinol and O-1812, a potent and metabolically stable anandamide analog, in rats". Experimental and Clinical Psychopharmacology 12 (3): 173–9. doi:10.1037/1064-1297.12.3.173. PMID 15301634. 
  4. ^ Wiley JL, Smith FL, Razdan RK, Dewey WL (March 2005). "Task specificity of cross-tolerance between Delta9-tetrahydrocannabinol and anandamide analogs in mice". European Journal of Pharmacology 510 (1-2): 59–68. doi:10.1016/j.ejphar.2005.01.006. PMID 15740725. 
  5. ^ Breivogel CS, Lambert JM, Gerfin S, Huffman JW, Razdan RK (July 2008). "Sensitivity to delta9-tetrahydrocannabinol is selectively enhanced in beta-arrestin2 -/- mice". Behavioural Pharmacology 19 (4): 298–307. doi:10.1097/FBP.0b013e328308f1e6. PMC 2751575. PMID 18622177. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2751575. 


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