O-1812

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O-1812
O-1812 structure.png
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
Legal status ?
Identifiers
CAS number 342882-77-3 N
ATC code ?
PubChem CID 9823107
Chemical data
Formula C26H42N2O2 
Mol. mass 414.622 g/mol
 N (what is this?)  (verify)

O-1812 is an eicosanoid derivative related to anandamide that 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[edit]

References[edit]

  1. ^ Di Marzo V, et al. (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, et al. (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, et al. (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.