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Merck
CN

D8555

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:
Molecular Weight:
436.60
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
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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

SMILES string

CCCCCCN(CCCCCC)C(=O)Cc1c([nH]c2ccccc12)-c3ccc(F)cc3

InChI key

VUWXAQFLTSBUDB-UHFFFAOYSA-N

form

powder

solubility

methanol: 50 mg/mL, H2O: insoluble

storage temp.

2-8°C

Quality Level

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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
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
Antonio F Santidrián et al.
Haematologica, 92(12), 1631-1638 (2007-12-07)
The potential anticancer agent 1-(2-chlorophenyl-N-methylpropyl)-3-isoquinolinecarboxamide (PK11195), a translocator protein (18KDa) (TSPO) ligand, facilitates the induction of cell death by a variety of cytotoxic and chemotherapeutic agents. Primary chronic lymphocytic leukemia (CLL) cells overexpress TSPO. The aim of this study was
Cheryl A Frye et al.
Reproduction (Cambridge, England), 137(1), 119-128 (2008-09-27)
The progesterone metabolite and neurosteroid, 5alpha-pregnan-3alpha-ol-20-one (3alpha,5alpha-THP), has actions in the midbrain ventral tegmental area (VTA) to modulate lordosis, but its effects on other reproductively relevant behaviors are not well understood. Effects on exploration, anxiety, and social behavior resulting from
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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