O-1812

O-1812
Identifiers
	IUPAC name (5Z,8Z,11Z,14Z)-20-cyano-N-[(2R)-1-hydroxypropan-2-yl]-16,16-dimethylicosa-5,8,11,14-tetraenamide;
CAS Number	342882-77-3 ;
PubChem CID	9823107;
IUPHAR/BPS	732;
ChemSpider	7998855 ;
UNII	5766D7AFA7;
CompTox Dashboard (EPA)	DTXSID80745442 ;
Chemical and physical data
Formula	C26H42N2O2
Molar mass	414.634 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H](CO)NC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C(C)(C)CCCCC#N;
	InChI InChI=1S/C26H42N2O2/c1-24(23-29)28-25(30)19-15-12-10-8-6-4-5-7-9-11-13-16-20-26(2,3)21-17-14-18-22-27/h4-5,8-11,16,20,24,29H,6-7,12-15,17-19,21,23H2,1-3H3,(H,28,30)/b5-4-,10-8-,11-9-,20-16-/t24-/m1/s1 ; Key:WZQHSBKOWZOASP-QLZKPENWSA-N ;
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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 K_i of 3.4 nM at CB₁ and 3870 nM 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]

References

^ Di Marzo V, et al. (February 2001). "Highly selective CB₁ cannabinoid receptor ligands and novel CB₁/VR₁ vanilloid receptor "hybrid" ligands". Biochemical and Biophysical Research Communications. 281 (2): 444–51. doi:10.1006/bbrc.2001.4354. PMID 11181068.
^ Baskfield CY, Martin BR, Wiley JL (April 2004). "Differential effects of Δ⁹-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. S2CID 36621393.
^ Wiley JL, et al. (August 2004). "A comparison of the discriminative stimulus effects of Δ⁹-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.
^ Wiley JL, Smith FL, Razdan RK, Dewey WL (March 2005). "Task specificity of cross-tolerance between Δ⁹-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.
^ Breivogel CS, et al. (July 2008). "Sensitivity to Δ⁹-tetrahydrocannabinol is selectively enhanced in β-arrestin2 -/- mice". Behavioural Pharmacology. 19 (4): 298–307. doi:10.1097/FBP.0b013e328308f1e6. PMC 2751575. PMID 18622177.

[pmid11181068-1] Di Marzo V, et al. (February 2001). "Highly selective CB₁ cannabinoid receptor ligands and novel CB₁/VR₁ vanilloid receptor "hybrid" ligands". Biochemical and Biophysical Research Communications. 281 (2): 444–51. doi:10.1006/bbrc.2001.4354. PMID 11181068.

[pmid14718593-2] Baskfield CY, Martin BR, Wiley JL (April 2004). "Differential effects of Δ⁹-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. S2CID 36621393.

[pmid15301634-3] Wiley JL, et al. (August 2004). "A comparison of the discriminative stimulus effects of Δ⁹-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.

[pmid15740725-4] Wiley JL, Smith FL, Razdan RK, Dewey WL (March 2005). "Task specificity of cross-tolerance between Δ⁹-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.

[pmid18622177-5] Breivogel CS, et al. (July 2008). "Sensitivity to Δ⁹-tetrahydrocannabinol is selectively enhanced in β-arrestin2 -/- mice". Behavioural Pharmacology. 19 (4): 298–307. doi:10.1097/FBP.0b013e328308f1e6. PMC 2751575. PMID 18622177.

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[5]

See also

References