FGIN-127

FGIN-127
Identifiers
	IUPAC name 2-[2-(4-fluorophenyl)-1H-indol-3-yl]-N,N-dihexylacetamide;
CAS Number	142720-24-9 ;
PubChem CID	132496;
ChemSpider	116994 ;
ChEBI	CHEBI:92171 ;
CompTox Dashboard (EPA)	DTXSID90162141 ;
Chemical and physical data
Formula	C28H37FN2O
Molar mass	436.615 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCN(CCCCCC)C(=O)Cc1c2ccccc2[nH]c1c3ccc(cc3)F;
	InChI InChI=1S/C28H37FN2O/c1-3-5-7-11-19-31(20-12-8-6-4-2)27(32)21-25-24-13-9-10-14-26(24)30-28(25)22-15-17-23(29)18-16-22/h9-10,13-18,30H,3-8,11-12,19-21H2,1-2H3 ; Key:VUWXAQFLTSBUDB-UHFFFAOYSA-N ;
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FGIN-1-27 is an anxiolytic drug which acts as a selective agonist at the peripheral benzodiazepine receptor, also known as the mitochondrial 18 kDa translocator protein or TSPO. It is thought to produce anxiolytic effects by stimulating steroidogenesis of neuroactive steroids such as allopregnanolone.^[1]^[2]^[3]^[4]^[5]^[6]

References

^ Romeo E, Auta J, Kozikowski AP, Ma D, Papadopoulos V, Puia G, Costa E, Guidotti A (September 1992). "2-Aryl-3-indoleacetamides (FGIN-1): a new class of potent and specific ligands for the mitochondrial DBI receptor (MDR)". The Journal of Pharmacology and Experimental Therapeutics. 262 (3): 971–8. PMID 1326631.
^ Romeo E, Cavallaro S, Korneyev A, Kozikowski AP, Ma D, Polo A, Costa E, Guidotti A (October 1993). "Stimulation of brain steroidogenesis by 2-aryl-indole-3-acetamide derivatives acting at the mitochondrial diazepam-binding inhibitor receptor complex". The Journal of Pharmacology and Experimental Therapeutics. 267 (1): 462–71. PMID 8229777.
^ Guillon J, Boulouard M, Lelong V, Dallemagne P, Rault S, Jarry C (November 2001). "Synthesis and preliminary behavioural evaluation in mice of new 3-aryl-3-pyrrol-1-ylpropanamides, analogues of FGIN-1-27 and FGIN-1-43". The Journal of Pharmacy and Pharmacology. 53 (11): 1561–8. doi:10.1211/0022357011777945. PMID 11732760. S2CID 11838769.
^ Petralia SM, Frye CA (March 2005). "In the ventral tegmental area picrotoxin blocks FGIN 1-27-induced increases in sexual behavior of rats and hamsters". Psychopharmacology. 178 (2–3): 174–82. doi:10.1007/s00213-004-2001-9. PMID 15338106. S2CID 22649389.
^ Opatz T, Ferenc D (September 2006). "Preparation of indoles from alpha-aminonitriles: A short synthesis of FGIN-1-27". Organic Letters. 8 (20): 4473–5. doi:10.1021/ol061617+. PMID 16986928.
^ James ML, Selleri S, Kassiou M (2006). "Development of ligands for the peripheral benzodiazepine receptor" (PDF). Current Medicinal Chemistry. 13 (17): 1991–2001. doi:10.2174/092986706777584979. hdl:2158/222808. PMID 16842193.

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[pmid1326631-1] Romeo E, Auta J, Kozikowski AP, Ma D, Papadopoulos V, Puia G, Costa E, Guidotti A (September 1992). "2-Aryl-3-indoleacetamides (FGIN-1): a new class of potent and specific ligands for the mitochondrial DBI receptor (MDR)". The Journal of Pharmacology and Experimental Therapeutics. 262 (3): 971–8. PMID 1326631.

[pmid8229777-2] Romeo E, Cavallaro S, Korneyev A, Kozikowski AP, Ma D, Polo A, Costa E, Guidotti A (October 1993). "Stimulation of brain steroidogenesis by 2-aryl-indole-3-acetamide derivatives acting at the mitochondrial diazepam-binding inhibitor receptor complex". The Journal of Pharmacology and Experimental Therapeutics. 267 (1): 462–71. PMID 8229777.

[pmid11732760-3] Guillon J, Boulouard M, Lelong V, Dallemagne P, Rault S, Jarry C (November 2001). "Synthesis and preliminary behavioural evaluation in mice of new 3-aryl-3-pyrrol-1-ylpropanamides, analogues of FGIN-1-27 and FGIN-1-43". The Journal of Pharmacy and Pharmacology. 53 (11): 1561–8. doi:10.1211/0022357011777945. PMID 11732760. S2CID 11838769.

[pmid15338106-4] Petralia SM, Frye CA (March 2005). "In the ventral tegmental area picrotoxin blocks FGIN 1-27-induced increases in sexual behavior of rats and hamsters". Psychopharmacology. 178 (2–3): 174–82. doi:10.1007/s00213-004-2001-9. PMID 15338106. S2CID 22649389.

[pmid16986928-5] Opatz T, Ferenc D (September 2006). "Preparation of indoles from alpha-aminonitriles: A short synthesis of FGIN-1-27". Organic Letters. 8 (20): 4473–5. doi:10.1021/ol061617+. PMID 16986928.

[pmid16842193-6] James ML, Selleri S, Kassiou M (2006). "Development of ligands for the peripheral benzodiazepine receptor" (PDF). Current Medicinal Chemistry. 13 (17): 1991–2001. doi:10.2174/092986706777584979. hdl:2158/222808. PMID 16842193.

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Identifiers

IUPAC name 2-[2-(4-fluorophenyl)-1H-indol-3-yl]-N,N-dihexylacetamide
CAS Number	142720-24-9^Y
PubChem CID	132496
ChemSpider	116994^N
ChEBI	CHEBI:92171^N
CompTox Dashboard (EPA)	DTXSID90162141
Chemical and physical data
Formula	C₂₈H₃₇FN₂O
Molar mass	436.615 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCCN(CCCCCC)C(=O)Cc1c2ccccc2[nH]c1c3ccc(cc3)F
InChI InChI=1S/C28H37FN2O/c1-3-5-7-11-19-31(20-12-8-6-4-2)27(32)21-25-24-13-9-10-14-26(24)30-28(25)22-15-17-23(29)18-16-22/h9-10,13-18,30H,3-8,11-12,19-21H2,1-2H3^N Key:VUWXAQFLTSBUDB-UHFFFAOYSA-N^N
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