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SML3009

Sigma-Aldrich

Indiplon

≥98% (HPLC)

Synonym(s):

CL 285,489, CL 285489, CL-285,489, CL-285489, CL285,489, CL285489, N-Methyl-N-(3-(3-(thiophene-2-carbonyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)acetamide, N-Methyl-N-[3-[3-(2-thienylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]acetamide, NBI 34060, NBI-34060, NBI34060

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About This Item

Empirical Formula (Hill Notation):
C20H16N4O2S
CAS Number:
325715-02-4
Molecular Weight:
376.43
MDL number:
MFCD09264193
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

[s]1c(ccc1)C(=O)c2c3[n](nc2)C(=CC=N3)c4cc(ccc4)N(C)C(=O)C

InChI

1S/C20H16N4O2S/c1-13(25)23(2)15-6-3-5-14(11-15)17-8-9-21-20-16(12-22-24(17)20)19(26)18-7-4-10-27-18/h3-12H,1-2H3

InChI key

CBIAWPMZSFFRGN-UHFFFAOYSA-N

Biochem/physiol Actions

Indiplon (NBI 34060) is an orally active, high-affinity GABAA receptor positive allosteric modulator (PAM) with preferential labeling of alpha1 subunits-containing receptors (rat cerebellar/cerebral cortex membranes binding KD = 1.01/0.45 nM). Indiplon potentiates GABA-induced chloride conductance of cultured rat cortical neurons (EC50 = 11.6 nM vs 152 nM/630 nM) and exhibits sedative efficacy in mice (ED50 = 1 mg/kg/passive avoidance & 2.7 mg/kg/locomotor activity inhibition po.) and rats (ED50 = 2.5 mg/kg/locomotor activity inhibition & 3 mg/kg/vigilance impairment po.) in vivo. Indiplon shows greater affinity, in vitor and in vivo potency than zaleplon and zolpidem.
Orally active, high-affinity GABA(A) receptor positive allosteric modulator (PAM) with in vivo sedative-hypnotic efficacy.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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D K Cass et al.
Molecular psychiatry, 19(5), 536-543 (2014-03-05)
Converging epidemiological studies indicate that cannabis abuse during adolescence increases the risk of developing psychosis and prefrontal cortex (PFC)-dependent cognitive impairments later in life. However, the mechanisms underlying the adolescent susceptibility to chronic cannabis exposure are poorly understood. Given that
Alan C Foster et al.
The Journal of pharmacology and experimental therapeutics, 311(2), 547-559 (2004-07-17)
Indiplon (NBI 34060; N-methyl-N-[3-[3-(2-thienylcarbonyl)-pyrazolo[1,5-alpha]pyrimidin-7-yl]phenyl]acetamide), a novel pyrazolopyrimidine and high-affinity allosteric potentiator of GABA(A) receptor function, was profiled for its effects in rodents after oral administration. In mice, indiplon inhibited locomotor activity (ED(50) = 2.7 mg/kg p.o.) at doses lower than
Ignacio Vega-Quiroga et al.
Neuropharmacology, 128, 76-85 (2017-10-01)
The mechanisms commanding the activity of dopaminergic neurons of the ventral tegmental area (VTA) and the location of these neurons are relevant for the coding and expression of motivated behavior associated to reward-related signals. Anatomical evidence shows that several brain
Yanbo Jiang et al.
Neuropharmacology, 138, 97-105 (2018-06-09)
Ionotropic GABAA receptors expressing at the axon initial segment (AIS) of glutamatergic pyramidal cell (PC) in the cortex plays critical roles in regulating action potential generation. However, it remains unclear whether these receptors also express at the AIS of cortical
Vatsala R Jayasinghe et al.
Cerebral cortex (New York, N.Y. : 1991), 27(1), 625-634 (2015-10-29)
The onset of motor deficits in parkinsonism is thought to result from dopamine (DA) loss-induced corticostriatal disruption and the development of excessive cortico-basal ganglia synchronization. To gain insights into the mechanisms underlying such corticostriatal dysfunction, we conducted local field potential
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