CL-218,872

CL-218,872
Identifiers
IUPAC name
  • 3-methyl-6-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[3,4-f]pyridazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.164.099 Edit this at Wikidata
Chemical and physical data
FormulaC13H9F3N4
Molar mass278.238 g·mol−1
InChI
  • InChI=1S/C13H9F3N4/c1-8-17-18-12-6-5-11(19-20(8)12)9-3-2-4-10(7-9)13(14,15)16/h2-7H,1H3 checkY
  • Key:GUOQUXNJZHGPQF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

CL-218,872 is a sedative and hypnotic drug used in scientific research.[1][2] It has similar effects to sedative-hypnotic benzodiazepine drugs such as triazolam, but is structurally distinct and so is classed as a nonbenzodiazepine hypnotic.

CL-218,872 is a GABAA partial agonist which is selective for the α1 subtype.[3][4][5] It has a range of effects including sedative, hypnotic, anxiolytic, anticonvulsant and amnestic actions, however the most prominent actions are sedation and amnesia, and CL-218,872 produces effects very similar to those of the hypnotic imidazopyridine derivative zolpidem in animal studies.[6][7][8]

References

  1. ↑ Moreau S, Coudert P, Rubat C, Gardette D, Vallee-Goyet D, Couquelet J, Bastide P, Tronche P (July 1994). "Synthesis and anticonvulsant properties of new benzylpyridazine derivatives". Journal of Medicinal Chemistry. 37 (14): 2153–60. doi:10.1021/jm00040a006. PMID 8035421.
  2. ↑ Karolak-Wojciechowska J, Lange J, Kwiatkowski W, Gniewosz M, Plenkiewicz J (August 1994). "Bicyclic [b]-heteroannulated pyridazine derivatives--II. Structure-activity relationships in the 6-aryltriazolo-[4,3-b]pyridazine ligands of the benzodiazepine receptor". Bioorganic & Medicinal Chemistry. 2 (8): 773–9. doi:10.1016/s0968-0896(00)82176-8. PMID 7894970.
  3. ↑ Hadingham KL, Wafford KA, Thompson SA, Palmer KJ, Whiting PJ (November 1995). "Expression and pharmacology of human GABAA receptors containing gamma 3 subunits". European Journal of Pharmacology. 291 (3): 301–9. doi:10.1016/0922-4106(95)90070-5. PMID 8719414.
  4. ↑ Araujo F, Tan S, Ruano D, Schoemaker H, Benavides J, Vitorica J (November 1996). "Molecular and pharmacological characterization of native cortical gamma-aminobutyric acidA receptors containing both alpha1 and alpha3 subunits". Journal of Biological Chemistry. 271 (44): 27902–11. doi:10.1074/jbc.271.44.27902. PMID 8910390.
  5. ↑ Atack JR, Smith AJ, Emms F, McKernan RM (March 1999). "Regional differences in the inhibition of mouse in vivo [3H]Ro 15-1788 binding reflect selectivity for alpha 1 versus alpha 2 and alpha 3 subunit-containing GABAA receptors". Neuropsychopharmacology. 20 (3): 255–62. doi:10.1016/S0893-133X(98)00052-9. PMID 10063485.
  6. ↑ Rowlett JK, Spealman RD, Lelas S, Cook JM, Yin W (January 2003). "Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABA(A)/alpha1 receptors". Psychopharmacology. 165 (3): 209–15. doi:10.1007/s00213-002-1275-z. PMID 12420154. S2CID 37632215.
  7. ↑ Tonkiss J, Shultz PL, Bonnie KE, Hudson JL, Duran P, Galler JR (December 2003). "Spatial learning deficits induced by muscimol and CL218,872: lack of effect of prenatal malnutrition". Nutritional Neuroscience. 6 (6): 379–87. doi:10.1080/10284150310001624200. PMID 14744042. S2CID 26974393.
  8. ↑ Mirza NR, Rodgers RJ, Mathiasen LS (March 2006). "Comparative cue generalization profiles of L-838, 417, SL651498, zolpidem, CL218,872, ocinaplon, bretazenil, zopiclone, and various benzodiazepines in chlordiazepoxide and zolpidem drug discrimination". The Journal of Pharmacology and Experimental Therapeutics. 316 (3): 1291–9. doi:10.1124/jpet.105.094003. PMID 16339395. S2CID 21913400.
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