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 ;
PubChem CID	5311134;
IUPHAR/BPS	1349;
ChemSpider	4470661 ;
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 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]

[1]

[2]

[3]

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 (of MT₃) Prazosin (of MT₃) S-20928 S-22153 S-24601 S-25567 S-26131
See also: Receptor/signaling modulators Adrenergics Dopaminergics Serotonergics Monoamine metabolism modulators

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
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

Related Articles