CL-218,872

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CL-218,872
CL-218,872.svg
Systematic (IUPAC) name
3-methyl-6-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[3,4-f]pyridazine
Identifiers
CAS Number 66548-69-4 N
PubChem CID: 107950
ChemSpider 97072 YesY
ChEMBL CHEMBL13662 YesY
Chemical data
Formula C13H9F3N4
Molecular mass 278.233 g/mol
  • 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 YesY
  • Key:GUOQUXNJZHGPQF-UHFFFAOYSA-N YesY
 NYesY (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. Synthesis and anticonvulsant properties of new benzylpyridazine derivatives. Journal of Medicinal Chemistry. 1994 Jul 8;37(14):2153-60.
  2. ↑ Karolak-Wojciechowska J, Lange J, Kwiatkowski W, Gniewosz M, Plenkiewicz J. Bicyclic [b]-heteroannulated pyridazine derivatives--II. Structure-activity relationships in the 6-aryltriazolo-[4,3-b]pyridazine ligands of the benzodiazepine receptor. Bioorganic and Medicinal Chemistry. 1994 Aug;2(8):773-9.
  3. ↑ Hadingham KL, Wafford KA, Thompson SA, Palmer KJ, Whiting PJ. Expression and pharmacology of human GABAA receptors containing gamma 3 subunits. European Journal of Pharmacology. 1995 Nov 30;291(3):301-9.
  4. ↑ Araujo F, Tan S, Ruano D, Schoemaker H, Benavides J, Vitorica J. Molecular and pharmacological characterization of native cortical gamma-aminobutyric acidA receptors containing both alpha1 and alpha3 subunits. Journal of Biological Chemistry. 1996 Nov 1;271(44):27902-11.
  5. ↑ Atack JR, Smith AJ, Emms F, McKernan RM. 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. 1999 Mar;20(3):255-62.
  6. ↑ Rowlett JK, Spealman RD, Lelas S, Cook JM, Yin W. Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABA(A)/alpha1 receptors. Psychopharmacology (Berlin). 2003 Jan;165(3):209-15.
  7. ↑ Tonkiss J, Shultz PL, Bonnie KE, Hudson JL, Duran P, Galler JR. Spatial learning deficits induced by muscimol and CL218,872: lack of effect of prenatal malnutrition. Nutritional Neuroscience. 2003 Dec;6(6):379-87.
  8. ↑ Mirza NR, Rodgers RJ, Mathiasen LS. Comparative cue generalization profiles of L-838, 417, SL651498, zolpidem, CL218,872, ocinaplon, bretazenil, zopiclone, and various benzodiazepines in chlordiazepoxide and zolpidem drug discrimination. Journal of Pharmacology and Experimental Therapeutics. 2006 Mar;316(3):1291-9.
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