O-2050

O-2050 is a drug that is a classical cannabinoid derivative, which acts as an antagonist for the CB1 receptor. This gives it an advantage in research over many commonly used cannabinoid antagonists, such as rimonabant, which at higher doses act as inverse agonists at CB1 as well as showing off-target effects. However, while O-2050 acts as a silent antagonist in vitro, some tests in vivo have suggested it may show agonist activity under certain circumstances.[1][2][3][4][5][6]

O-2050
Identifiers
IUPAC name
  • (6aR,10aR)-3-(1-Methanesulfonylamino-4-hexyn-6-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC23H31NO4S
Molar mass417.56 g·mol−1
3D model (JSmol)
SMILES
  • CC1=CC[C@@H]2[C@@H](C1)c3c(cc(cc3OC2(C)C)CC#CCCCNS(=O)(=O)C)O
InChI
  • InChI=1S/C23H31NO4S/c1-16-10-11-19-18(13-16)22-20(25)14-17(15-21(22)28-23(19,2)3)9-7-5-6-8-12-24-29(4,26)27/h10,14-15,18-19,24-25H,6,8-9,11-13H2,1-4H3/t18-,19-/m1/s1
  • Key:DJTGGIYZQHHLGJ-RTBURBONSA-N
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See also

References
  1. Martin BR, Stephenson LA, Pertwee RG, Breivogel CS, Williams W, Mahadevan A, Razdan RK (2002). "Agonists and silent antagonists in a series of cannabinoid sulfonamides" (PDF). 12th Annual Symposium on the Cannabinoids.
  2. US 7279500, Martin, Billy R.; Razdan, Raj K. & Pertwee, Roger G, "Sulfonamide cannabinoid agonists and antagonists", published 2007-10-09, assigned to Virginia Commonwealth University
  3. Gardner A, Mallet PE (January 2006). "Suppression of feeding, drinking, and locomotion by a putative cannabinoid receptor 'silent antagonist'". European Journal of Pharmacology. 530 (1–2): 103–6. doi:10.1016/j.ejphar.2005.11.032. PMID 16380113.
  4. Higuchi S, Irie K, Mishima S, Araki M, Ohji M, Shirakawa A, et al. (2010). "The cannabinoid 1-receptor silent antagonist O-2050 attenuates preference for high-fat diet and activated astrocytes in mice". Journal of Pharmacological Sciences. 112 (3): 369–72. doi:10.1254/jphs.09326sc. PMID 20168044.
  5. Higuchi S, Ohji M, Araki M, Furuta R, Katsuki M, Yamaguchi R, et al. (January 2011). "Increment of hypothalamic 2-arachidonoylglycerol induces the preference for a high-fat diet via activation of cannabinoid 1 receptors". Behavioural Brain Research. 216 (1): 477–80. doi:10.1016/j.bbr.2010.08.042. PMID 20817042. S2CID 29756189.
  6. Wiley JL, Breivogel CS, Mahadevan A, Pertwee RG, Cascio MG, Bolognini D, et al. (January 2011). "Structural and pharmacological analysis of O-2050, a putative neutral cannabinoid CB(1) receptor antagonist". European Journal of Pharmacology. 651 (1–3): 96–105. doi:10.1016/j.ejphar.2010.10.085. PMC 3034309. PMID 21114999.
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