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 Registry Number | 336615-64-6  |
| PubChem | CID: 9868408 |
| ChemSpider | 8044099  |
| Chemical data | |
| Formula | C22H22Cl3N3O |
| Molecular 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 homologue O-1270 and the N-propyl homologue O-1399 also act as cannabinoid agonists with similar potency in vivo, despite weaker binding affinity at cannabinoid receptors compared to the pentyl homologue 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]
- ^ Billy R. Martin, Raj K. Razdan, Anu Mahadevan. Pyrazole cannabinoid agonist and antagonists. US Patent 6509367, filed Sep 22, 2001, issued Jan 21, 2003.
- ^ Shim JY, Welsh WJ, Cartier E, Edwards JL, Howlett AC. 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. 2002 Mar 28;45(7):1447-59. PMID 11906286
- ^ Francisco ME, Seltzman HH, Gilliam AF, Mitchell RA, Rider SL, Pertwee RG, Stevenson LA, Thomas BF. 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. 2002 Jun 20;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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