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	66548-69-4  N
PubChem CID	107950
ChemSpider	97072  Y
UNII	O7GR5XL5B5
ChEMBL	ChEMBL13662  Y
CompTox Dashboard (EPA)	DTXSID80216728
ECHA InfoCard	100.164.099
Chemical and physical data
Formula	C13H9F3N4
Molar mass	278.238 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 Y Key:GUOQUXNJZHGPQF-UHFFFAOYSA-N Y
NY  (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 GABA_A 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.