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131733-92-1

131733-92-1 | Acetic acid, 2-(5,7,8,9-tetrahydro-5-hydroxy-6H-benzocyclohepten-6-ylidene)-, sodium salt (1:1)

CAS No: 131733-92-1 Catalog No: AG000ZMI MDL No:MFCD00270050

Product Description

Catalog Number:
AG000ZMI
Chemical Name:
Acetic acid, 2-(5,7,8,9-tetrahydro-5-hydroxy-6H-benzocyclohepten-6-ylidene)-, sodium salt (1:1)
CAS Number:
131733-92-1
Molecular Formula:
C13H13NaO3
Molecular Weight:
240.2303
MDL Number:
MFCD00270050
IUPAC Name:
sodium;(2E)-2-(5-hydroxy-5,7,8,9-tetrahydrobenzo[7]annulen-6-ylidene)acetate
InChI:
InChI=1S/C13H14O3.Na/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16;/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15);/q;+1/p-1/b10-8+;
InChI Key:
BTWDZCORIHHOPO-VRTOBVRTSA-M
SMILES:
[O-]C(=O)C=C1CCCc2c(C1O)cccc2.[Na+]

Properties

Complexity:
301  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
240.076g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
240.234g/mol
Monoisotopic Mass:
240.076g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
60.4A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0

Literature

Title Journal
Toxicologic/transport properties of NCS-382, a γ-hydroxybutyrate (GHB) receptor ligand, in neuronal and epithelial cells: Therapeutic implications for SSADH deficiency, a GABA metabolic disorder. Toxicology in vitro : an international journal published in association with BIBRA 20180201
In vitro toxicological evaluation of NCS-382, a high-affinity antagonist of γ-hydroxybutyrate (GHB) binding. Toxicology in vitro : an international journal published in association with BIBRA 20170401
Novel radioiodinated {gamma}-hydroxybutyric acid analogues for radiolabeling and Photolinking of high-affinity {gamma}-hydroxybutyric acid binding sites. The Journal of pharmacology and experimental therapeutics 20101101
Calcium and cAMP signaling induced by gamma-hydroxybutyrate receptor(s) stimulation in NCB-20 neurons. Neuroscience 20100428
Neurotoxic effects induced by gammahydroxybutyric acid (GHB) in male rats. The international journal of neuropsychopharmacology 20091001
Validation of high-affinity binding sites for succinic acid through distinguishable binding of gamma-hydroxybutyric acid receptor-specific NCS 382 antipodes. Bioorganic & medicinal chemistry letters 20081201
Characterization and pharmacology of the GHB receptor. Annals of the New York Academy of Sciences 20081001
Differentiating the discriminative stimulus effects of gamma-hydroxybutyrate and ethanol in a three-choice drug discrimination procedure in rats. Pharmacology, biochemistry, and behavior 20080601
Gamma-aminobutyric acidB (GABAB)-receptor mediation of different in vivo effects of gamma-butyrolactone. Journal of pharmacological sciences 20080201
[Effect of gamma-hydroxybutyric acid receptor on focal cerebral ischemia-reperfusion injury in rats]. Yao xue xue bao = Acta pharmaceutica Sinica 20070801
Metabolic GHB precursor succinate binds to gamma-hydroxybutyrate receptors: characterization of human basal ganglia areas nucleus accumbens and globus pallidus. Journal of neuroscience research 20060701
Succinate semialdehyde dehydrogenase deficiency does not down-regulate gamma-hydroxybutyric acid binding sites in the mouse brain. Molecular genetics and metabolism 20060501
Discriminative stimulus effects of flumazenil: perceptual masking by baclofen, and lack of substitution with gamma-hydroxybutyrate and its precursors 1,4-butanediol and gamma-butyrolactone. Behavioural pharmacology 20060501
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Novel cyclic gamma-hydroxybutyrate (GHB) analogs with high affinity and stereoselectivity of binding to GHB sites in rat brain. The Journal of pharmacology and experimental therapeutics 20051001
Drosophila GABA(B) receptors are involved in behavioral effects of gamma-hydroxybutyric acid (GHB). European journal of pharmacology 20050920
Involvement of gamma-hydroxybutyrate (GHB) and GABA-B receptors in the acute behavioral effects of GHB in baboons. Psychopharmacology 20050701
Discriminative stimulus effects of gamma-hydroxybutyrate (GHB) in rats discriminating GHB from baclofen and diazepam. The Journal of pharmacology and experimental therapeutics 20050701
Resuscitative effect of a gamma-aminobutyric acid B receptor antagonist on gamma-hydroxybutyric acid mortality in mice. Annals of emergency medicine 20050601
Mechanisms underlying the sympathomimetic cardiovascular responses elicited by gamma-hydroxybutyrate. Journal of cardiovascular pharmacology 20041201
Ethanol does not alter the binding of the gamma-hydroxybutyric acid (GHB) receptor ligand [3H]NCS-382 in the rat brain. Drug and alcohol dependence 20040906
4-Hydroxy-trans-2-nonenoic acid is a gamma-hydroxybutyrate receptor ligand in the cerebral cortex and hippocampus. Journal of neurochemistry 20040601
Gamma-hydroxybutyrate and ethanol depress spontaneous excitatory postsynaptic currents in dopaminergic neurons of the substantia nigra. Brain research 20040130
Effects of gamma-hydroxybutyrate (GHB) on schedule-controlled responding in rats: role of GHB and GABAB receptors. The Journal of pharmacology and experimental therapeutics 20040101
A review of pharmacology of NCS-382, a putative antagonist of gamma-hydroxybutyric acid (GHB) receptor. CNS drug reviews 20040101
Pathway-specific action of gamma-hydroxybutyric acid in sensory thalamus and its relevance to absence seizures. The Journal of neuroscience : the official journal of the Society for Neuroscience 20031210
Selective gamma-hydroxybutyric acid receptor ligands increase extracellular glutamate in the hippocampus, but fail to activate G protein and to produce the sedative/hypnotic effect of gamma-hydroxybutyric acid. Journal of neurochemistry 20031101
Specific gamma-hydroxybutyrate-binding sites but loss of pharmacological effects of gamma-hydroxybutyrate in GABA(B)(1)-deficient mice. The European journal of neuroscience 20031101
Quantitative autoradiographic analysis of the new radioligand [(3)H](2E)-(5-hydroxy-5,7,8,9-tetrahydro-6H-benzo[a][7]annulen-6-ylidene) ethanoic acid ([(3)H]NCS-382) at gamma-hydroxybutyric acid (GHB) binding sites in rat brain. Brain research 20030725
Interactions of gamma-hydroxy butyrate with ethanol and NCS 382. European journal of pharmacology 20030606
A tertiary alcohol analog of gamma-hydroxybutyric acid as a specific gamma-hydroxybutyric acid receptor ligand. The Journal of pharmacology and experimental therapeutics 20030501
Therapeutic intervention in mice deficient for succinate semialdehyde dehydrogenase (gamma-hydroxybutyric aciduria). The Journal of pharmacology and experimental therapeutics 20020701
Stereoselectivity of NCS-382 binding to gamma-hydroxybutyrate receptor in the rat brain. European journal of pharmacology 20020620
GABA(B)-receptor mediation of the inhibitory effect of gamma-hydroxybutyric acid on intestinal motility in mice. Life sciences 20020510
Effects of the putative antagonist NCS382 on the behavioral pharmacological actions of gammahydroxybutyrate in mice. Psychopharmacology 20020201
Binding characteristics of the gamma-hydroxybutyric acid receptor antagonist [(3)H](2E)-(5-hydroxy-5,7,8,9-tetrahydro-6H-benzo[a][7]annulen-6-ylidene) ethanoic acid in the rat brain. The Journal of pharmacology and experimental therapeutics 20011201
gamma-Hydroxybutyric acid and baclofen decrease extracellular acetylcholine levels in the hippocampus via GABA(B) receptors. European journal of pharmacology 20011102
Role of GABA(B) receptors in the sedative/hypnotic effect of gamma-hydroxybutyric acid. European journal of pharmacology 20011012
gamma-Hydroxybutyrate modulation of glutamate levels in the hippocampus: an in vivo and in vitro study. Journal of neurochemistry 20010901

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