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D8555

Sigma-Aldrich

N,N-Dihexyl-2-(4-fluorophenyl)indole-3-acetamide

Synonym(s):

FGIN-1-27

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About This Item

Empirical Formula (Hill Notation):
C28H37FN2O
CAS Number:
142720-24-9
Molecular Weight:
436.60
MDL number:
MFCD00467704
UNSPSC Code:
12352200
PubChem Substance ID:
24278393
NACRES:
NA.77

form

powder

Quality Level

200

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

Certificates of Analysis (COA)

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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
Dandan Zhou et al.
Journal of molecular neuroscience : MN, 70(4), 542-549 (2019-12-28)
Microglia activation has been reported to be associated with pathogenesis of neuroinflammation, central nervous system damage, and degeneration diseases. With various damage-associated molecules released, M1 polarization of microglia emerges early after injury and followed by M2 polarization. In this study
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
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