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GS-39783

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Chemical compound

Pharmaceutical compound

GS-39783
Identifiers

IUPAC name N,N-Dicyclopentyl-2-methylsulfanyl-5-nitropyrimidine-4,6-diamine
CAS Number	39069-52-8^Y
PubChemCID	6604928
IUPHAR/BPS	5446
ChemSpider	5037184^N
UNII	HD3T22A5DM
CompTox Dashboard(EPA)	DTXSID30424992
ECHA InfoCard	100.164.558
Chemical and physical data
Formula	C₁₅H₂₃N₅O₂S
Molar mass	337.44 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C3CCCC3Nc1nc(SC)nc(c1N(=O)=O)NC2CCCC2
InChI InChI=1S/C15H23N5O2S/c1-23-15-18-13(16-10-6-2-3-7-10)12(20(21)22)14(19-15)17-11-8-4-5-9-11/h10-11H,2-9H2,1H3,(H2,16,17,18,19)^N Key:GSGVDKOCBKBMGG-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

GS-39783 is a compound used in scientific research which acts as apositive allosteric modulator at theGABA_B receptor.^[1]^[2] It has been shown to produceanxiolytic effects in animal studies,^[3]^[4]^[5] and reduces self-administration ofalcohol,^[6]^[7]cocaine^[8]^[9]^[10] andnicotine.^[11]

References

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^Urwyler S, Pozza MF, Lingenhoehl K, Mosbacher J, Lampert C, Froestl W, et al. (October 2003). "N,N'-Dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine (GS39783) and structurally related compounds: novel allosteric enhancers of gamma-aminobutyric acidB receptor function".The Journal of Pharmacology and Experimental Therapeutics.307 (1):322–30.doi:10.1124/jpet.103.053074.PMID 12954816.
^Guery S, Floersheim P, Kaupmann K, Froestl W (November 2007)."Syntheses and optimization of new GS39783 analogues as positive allosteric modulators of GABA B receptors".Bioorganic & Medicinal Chemistry Letters.17 (22):6206–11.doi:10.1016/j.bmcl.2007.09.023.PMC 2278029.PMID 17884493.
^Mombereau C, Kaupmann K, Froestl W, Sansig G, van der Putten H, Cryan JF (June 2004)."Genetic and pharmacological evidence of a role for GABA(B) receptors in the modulation of anxiety- and antidepressant-like behavior".Neuropsychopharmacology.29 (6):1050–62.doi:10.1038/sj.npp.1300413.PMID 15039762.
^Cryan JF, Kelly PH, Chaperon F, Gentsch C, Mombereau C, Lingenhoehl K, et al. (September 2004). "Behavioral characterization of the novel GABAB receptor-positive modulator GS39783 (N,N'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine): anxiolytic-like activity without side effects associated with baclofen or benzodiazepines".The Journal of Pharmacology and Experimental Therapeutics.310 (3):952–63.doi:10.1124/jpet.104.066753.PMID 15113848.
^Jacobson LH, Cryan JF (April 2008). "Evaluation of the anxiolytic-like profile of the GABAB receptor positive modulator CGP7930 in rodents".Neuropharmacology.54 (5):854–62.doi:10.1016/j.neuropharm.2008.01.004.PMID 18328507.
^Orrù A, Lai P, Lobina C, Maccioni P, Piras P, Scanu L, et al. (November 2005). "Reducing effect of the positive allosteric modulators of the GABA(B) receptor, CGP7930 and GS39783, on alcohol intake in alcohol-preferring rats".European Journal of Pharmacology.525 (1–3):105–11.doi:10.1016/j.ejphar.2005.10.005.PMID 16289452.
^Maccioni P, Pes D, Orrù A, Froestl W, Gessa GL, Carai MA, Colombo G (August 2007). "Reducing effect of the positive allosteric modulator of the GABA(B) receptor, GS39,783, on alcohol self-administration in alcohol-preferring rats".Psychopharmacology.193 (2):171–8.doi:10.1007/s00213-007-0776-1.PMID 17393141.
^Smith MA, Yancey DL, Morgan D, Liu Y, Froestl W, Roberts DC (April 2004). "Effects of positive allosteric modulators of the GABAB receptor on cocaine self-administration in rats".Psychopharmacology.173 (1–2):105–11.doi:10.1007/s00213-003-1706-5.PMID 14712341.
^Slattery DA, Markou A, Froestl W, Cryan JF (November 2005)."The GABAB receptor-positive modulator GS39783 and the GABAB receptor agonist baclofen attenuate the reward-facilitating effects of cocaine: intracranial self-stimulation studies in the rat".Neuropsychopharmacology.30 (11):2065–72.doi:10.1038/sj.npp.1300734.PMID 15841108.
^Lhuillier L, Mombereau C, Cryan JF, Kaupmann K (February 2007)."GABA(B) receptor-positive modulation decreases selective molecular and behavioral effects of cocaine".Neuropsychopharmacology.32 (2):388–98.doi:10.1038/sj.npp.1301102.PMC 1774586.PMID 16710312.
^Paterson NE, Vlachou S, Guery S, Kaupmann K, Froestl W, Markou A (July 2008)."Positive modulation of GABA(B) receptors decreased nicotine self-administration and counteracted nicotine-induced enhancement of brain reward function in rats".The Journal of Pharmacology and Experimental Therapeutics.326 (1):306–14.doi:10.1124/jpet.108.139204.PMC 2574924.PMID 18445779.