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GR-196,429

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Chemical compound

Pharmaceutical compound

GR-196,429
Identifiers

IUPAC name N-[2-(2,3,7,8-tetrahydrofuro[2,3-g]indol-1-yl)ethyl]acetamide
CAS Number	170729-12-1^Y
PubChemCID	5311134
IUPHAR/BPS	1349
ChemSpider	4470661^Y
CompTox Dashboard(EPA)	DTXSID401030521
Chemical and physical data
Formula	C₁₄H₁₈N₂O₂
Molar mass	246.310 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c23c1CCOc1ccc2CCN3CCNC(=O)C
InChI InChI=1S/C14H18N2O2/c1-10(17)15-6-8-16-7-4-11-2-3-13-12(14(11)16)5-9-18-13/h2-3H,4-9H2,1H3,(H,15,17) Key:LTYWTNUOUBBVNZ-UHFFFAOYSA-N

GR-196,429 is amelatonin receptor agonist with some selectivity for the MT₁ subtype. It was one of the first synthetic melatonin agonists developed and continues to be used in scientific research, though it has never been developed for medical use. Studies in mice have shown GR-196,429 to produce both sleep-promoting effects and alterations ofcircadian rhythm, as well as stimulatingmelatonin release.^[1]^[2]^[3]

References

[edit]

^Beresford IJ, Browning C, Starkey SJ, Brown J, Foord SM, Coughlan J, et al. (June 1998). "GR196429: a nonindolic agonist at high-affinity melatonin receptors".The Journal of Pharmacology and Experimental Therapeutics.285 (3):1239–45.doi:10.1016/S0022-3565(24)37534-2.PMID 9618428.
^Beresford IJ, Harvey FJ, Hall DA, Giles H (November 1998). "Pharmacological characterisation of melatonin mt1 receptor-mediated stimulation of [35S]-GTPgammaS binding".Biochemical Pharmacology.56 (9):1167–74.doi:10.1016/s0006-2952(98)00254-8.PMID 9802327.
^Drijfhout WJ, de Vries JB, Homan EJ, Brons HF, Copinga S, Gruppen G, et al. (October 1999). "Novel non-indolic melatonin receptor agonists differentially entrain endogenous melatonin rhythm and increase its amplitude".European Journal of Pharmacology.382 (3):157–66.doi:10.1016/s0014-2999(99)00619-6.PMID 10556666.

v t e Melatonin receptor modulators
MT₁Tooltip Melatonin receptor 1	Agonists:2-Iodomelatonin 6-Hydroxymelatonin Agomelatine Fabomotizole (afobazole) GR-196,429 Melatonin N-Acetylserotonin (normelatonin) Piromelatine Ramelteon Tasimelteon TIK-301 (LY-156,735) Antagonists:Luzindole
MT₂Tooltip Melatonin receptor 2	Agonists:2-Iodomelatonin 6-Hydroxymelatonin Agomelatine GR-196,429 Melatonin N-Acetylserotonin (normelatonin) Piromelatine Ramelteon Tasimelteon TIK-301 (LY-156,735) Antagonists:Luzindole
Unsorted	Agonists:2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin 8-M-PDOT AMMTC GR-135,531 (of MT₃Tooltip melatonin receptor 1C) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin S-24268 S-25150 Antagonists:4-P-ADOT 4-P-PDOT DH-97 N-Acetyltryptamine (ofMT₃) Prazosin (ofMT₃) S-20928 S-22153 S-24601 S-25567 S-26131
See also:Receptor/signaling modulators Adrenergics Dopaminergics Serotonergics Monoamine metabolism modulators

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