GR-196,429

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
PubChem (CID)	5311134
IUPHAR/BPS	1349
Chemical and physical data
Formula	C₁₄H₁₈N₂O₂
Molar mass	246.308
3D model (Jmol)	Interactive image
SMILES c23c1CCOc1ccc2CCN3CCNC(=O)C

GR-196,429 is a melatonin 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 of circadian rhythm, as well as stimulating melatonin release.^[1]^[2]^[3]

References

↑ Beresford IJ, Browning C, Starkey SJ, Brown J, Foord SM, Coughlan J, North PC, Dubocovich ML, Hagan RM. GR196429: a nonindolic agonist at high-affinity melatonin receptors. Journal of Pharmacology and Experimental Therapeutics. 1998 Jun;285(3):1239-45. PMID 9618428
↑ Beresford IJ, Harvey FJ, Hall DA, Giles H. Pharmacological characterisation of melatonin mt1 receptor-mediated stimulation of [35S]-GTPgammaS binding. Biochemical Pharmacology. 1998 Nov 1;56(9):1167-74. PMID 9802327
↑ Drijfhout WJ, de Vries JB, Homan EJ, Brons HF, Copinga S, Gruppen G, Beresford IJ, Hagan RM, Grol CJ, Westerink BH. Novel non-indolic melatonin receptor agonists differentially entrain endogenous melatonin rhythm and increase its amplitude. European Journal of Pharmacology. 1999 Oct 15;382(3):157-66. PMID 10556666

Melatonin receptor modulators

MTR	Agonists: 2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin 8-M-PDOT Agomelatine AMMTC GR-135,531 (of MT₃) GR-196,429 Melatonin N-Acetylserotonin (normelatonin) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine Ramelteon S-24268 S-25150 Tasimelteon TIK-301 (LY-156,735) Antagonists: 4-P-ADOT 4-P-PDOT Afobazole DH-97 Luzindole N-Acetyltryptamine (of MT₃) Prazosin (of MT₃) S-20928 S-22153 S-24601 S-25567 S-26131

See also: Adrenergics Dopaminergics Serotonergics Monoamine reuptake and release modulators Monoamine metabolism modulators Monoamine neurotoxins

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