D8555
N,N-Dihexyl-2-(4-fluorophenyl)indole-3-acetamide
Synonym(s):
FGIN-1-27
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C28H37FN2O
CAS Number:
Molecular Weight:
436.60
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
form
powder
Quality Level
solubility
methanol: 50 mg/mL
H2O: insoluble
storage temp.
2-8°C
SMILES string
CCCCCCN(CCCCCC)C(=O)Cc1c([nH]c2ccccc12)-c3ccc(F)cc3
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
InChI key
VUWXAQFLTSBUDB-UHFFFAOYSA-N
Gene Information
human ... BZRAP1(9256)
rat ... Tspo(24230)
Biochem/physiol Actions
High affinity ligand for glial mitochondrial benzodiazepine receptors; stimulates neurosteroid biosynthesis; does not bind GABAA receptors
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Kazuhiro Tokuda et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(50), 16788-16795 (2010-12-17)
Benzodiazepines (BDZs) enhance GABA(A) receptor inhibition by direct actions on central BDZ receptors (CBRs). Although some BDZs also bind mitochondrial receptors [translocator protein (18 kDa) (TSPO)] and promote the synthesis of GABA-enhancing neurosteroids, the role of neurosteroids in the clinical
Cheryl A Frye et al.
Neuroendocrinology, 77(1), 71-82 (2003-03-08)
Progestins modulate lordosis through actions in the ventral tegmental area (VTA). Whether neurosteroidogenesis of 5alpha-pregnan-3alpha-ol-20-one (3alpha,5alpha-THP), involving mitochondrial benzodiazepine receptors (MBR), is important for lordosis was investigated. Ovariectomized (Ovx), hormone-primed rats (experiments 1, 3, 5, 6) and rats in behavioral
A P Sutter et al.
British journal of cancer, 89(3), 564-572 (2003-07-31)
Specific ligands of the peripheral benzodiazepine receptor (PBR) are known to induce apoptosis and cell cycle arrest in oesophageal cancer cells. However, the underlying mechanisms are still unknown. Here, we investigated the transcriptional alterations and activation of protein kinases in
E Romeo et al.
The Journal of pharmacology and experimental therapeutics, 267(1), 462-471 (1993-10-01)
The 2-aryl-indole-3-acetamide derivatives, 2-hexyl-indole-3-acetamide (FGIN-1-27) and 2-hexyl-indole-3-acetamide-N-benzene-tricarboxylic acid (FGIN-1-44) displaced [3H]1-(2-chlorophenyl)-N-methyl-N-(1- methylpropyl)-3-isoquinoline-carboxamide([3H]PK 11195) and [3H]4-chlorodiazepam ([3H]4'CD) from binding sites located on the rat brain mitochondrial DBI receptor complex (MDRC) with Ki values in the nanomolar range. Both 2-aryl-indole-3-acetamide derivatives acted
F M Freeman et al.
Pharmacology, biochemistry, and behavior, 67(2), 355-362 (2000-12-22)
The specific mitochondrial benzodiazepine receptor (MBR) agonist, FGIN 1-27, and antagonist, PK 11195, were used to investigate whether this receptor was involved in passive avoidance memory formation in the day-old chick. PK 11195 at a concentration of 1-10 microM was
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