O-1269
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| Systematic (IUPAC) name | |
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5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-pentylpyrazole-3-carboxamide
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| Identifiers | |
| CAS Number | 336615-64-6  |
| PubChem | CID 9868408 |
| ChemSpider | 8044099  |
| Chemical data | |
| Formula | C22H22Cl3N3O |
| Molar mass | 450.788 g/mol |
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O-1269 is a drug that is a diarylpyrazole derivative, related to potent cannabinoid antagonist drugs such as rimonabant and surinabant. However O-1269 and several related drugs were unexpectedly found to act as full or partial agonists at the cannabinoid receptors rather than antagonists, and so produce the usual effects expected of cannabinoid agonists in animal tests, such as sedation and analgesic effects. The N-heptyl homolog O-1270 and the N-propyl homolog O-1399 also act as cannabinoid agonists with similar potency in vivo, despite weaker binding affinity at cannabinoid receptors compared to the pentyl homolog O-1269.[1][2][3] Agonist-like and atypical cannabinoid activity has also been observed with a number of related compounds.[4][5]
References[edit]
- ^ US 6509367, Billy R. Martin, Raj K. Razdan, Anu Mahadevan, "Pyrazole cannabinoid agonist and antagonists"
- ^ Shim, J. Y.; Welsh, W. J.; Cartier, E; Edwards, J. L.; Howlett, A. C. (2002). "Molecular interaction of the antagonist N-(piperidin-1-yl)-5-(4-chlorophenyl)-1- (2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide with the CB1 cannabinoid receptor". Journal of medicinal chemistry. 45 (7): 1447–59. PMID 11906286.
- ^ Francisco, M. E.; Seltzman, H. H.; Gilliam, A. F.; Mitchell, R. A.; Rider, S. L.; Pertwee, R. G.; Stevenson, L. A.; Thomas, B. F. (2002). "Synthesis and structure-activity relationships of amide and hydrazide analogues of the cannabinoid CB(1) receptor antagonist N-(piperidinyl)- 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716)". Journal of medicinal chemistry. 45 (13): 2708–19. PMID 12061874.
- ^ Thomas, B. F.; Francisco, M. E. Y.; Seltzman, H. H.; Thomas, J. B.; Fix, S. E.; Schulz, A. K.; Gilliam, A. F.; Pertwee, R. G.; Stevenson, L. A. (2005). "Synthesis of long-chain amide analogs of the cannabinoid CB1 receptor antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) with unique binding selectivities and pharmacological activities". Bioorganic & Medicinal Chemistry. 13 (18): 5463–5474. doi:10.1016/j.bmc.2005.06.005. PMID 15994087.
- ^ Wiley, J. L.; Selley, D. E.; Wang, P.; Kottani, R.; Gadthula, S.; Mahadeven, A. (2011). "3-Substituted Pyrazole Analogs of the Cannabinoid Type 1 (CB1) Receptor Antagonist Rimonabant: Cannabinoid Agonist-Like Effects in Mice via Non-CB1, Non-CB2 Mechanism". Journal of Pharmacology and Experimental Therapeutics. 340 (2): 433–444. doi:10.1124/jpet.111.187815. PMC 3263966
. PMID 22085649.
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