FGIN-127

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]

FGIN-127
Identifiers
IUPAC name
  • 2-[2-(4-fluorophenyl)-1H-indol-3-yl]-N,N-dihexylacetamide
CAS Number
PubChem CID
ChemSpider
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H37FN2O
Molar mass436.615 g·mol−1
3D model (JSmol)
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
 NY (what is this?)  (verify)

References
  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.
  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.
  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.
  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.
  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.
  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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