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SML0249

Sigma-Aldrich

βCCt

≥98% (HPLC)

Synonym(s):

β-Carboline-3-carboxylate-t-Bu ester, beta-Carboline-3-carboxylate-t-butyl ester, tert-Butyl β-carboline-3-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C16H16N2O2
CAS Number:
93835-05-3
Molecular Weight:
268.31
MDL number:
MFCD06407911
UNSPSC Code:
12352200
PubChem Substance ID:
329825259

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)c1cc2c(cn1)[nH]c3ccccc23

InChI

1S/C16H16N2O2/c1-16(2,3)20-15(19)13-8-11-10-6-4-5-7-12(10)18-14(11)9-17-13/h4-9,18H,1-3H3

InChI key

FVFFDKKTXYVCCW-UHFFFAOYSA-N

Biochem/physiol Actions

βCCt has been characterized as an α1selective antagonist and benzodiazepine mixed agonist/antagonist.. A recent study found Ki values for the GABA-A subtypes were 0.72, 15, 18.9, 110.8, and >5,000 nM at five recombinant GABAA/BzR subtypes α1, α2, α3, α5, and α6 respectively. βCCt was a near ‘neutral′ antagonist (i.e., little or no efficacy) at all these 5 recombnant GABAA/BzR receptor subtypes. βCCt has been shown to reduce alcohol self-administration in alcohol preferring (P) and high alcohol drinking (HAD) rats.
βCCt is a GABBA antagonist selective for α1 subtype and a mixed benzodiazepine agonist-antagonist

Features and Benefits

This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
022M4601V

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Miroslav M Savić et al.
Phytotherapy research : PTR, 24(9), 1309-1316 (2010-02-04)
We performed a basic behavioral characterization of methanol extracts of four Balkan endemic Stachys taxa: S. anisochila (SA), S. beckeana (SB), S. plumosa (SP) and S. alpina subsp. dinarica (SAD). The behavioral activity of extracts dosed intraperitoneally in the range
Miroslav M Savić et al.
Behavioural brain research, 158(2), 293-300 (2005-02-09)
Recent research on genetically modified mice has attributed the amnesic effect of benzodiazepines mainly to the alpha1-containing GABA(A) receptor subtypes. The pharmacological approach, using subtype selective ligands, is needed to complement genetic studies. We tested the effects of the non-selective
Harry L June et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 32(1), 137-152 (2006-05-20)
The present study investigated the role of the alpha1-containing GABA(A) receptors in the neurobehavioral actions of alcohol. In Experiment 1, mice lacking the alpha1 subunit (alpha1 (-/-)) were tested for their capacity to initiate operant-lever press responding for alcohol or
T M DeLorey et al.
European journal of pharmacology, 426(1-2), 45-54 (2001-08-30)
Eight compounds that bind to the benzodiazepine binding site on the gamma-amino butyric acid(A) (GABA(A)) receptor were assessed for their influence on contextual memory, an aspect of memory affected in various cognitive disorders including Alzheimer's disease. Using a Pavlovian fear-conditioning
Harry L June et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 28(12), 2124-2137 (2003-09-12)
It has been hypothesized that alcohol addiction is mediated, at least in part, by specific gamma-aminobutyric acid(A) (GABA(A)) receptors within the ventral pallidum (VP). Among the potential GABA(A) receptor isoforms regulating alcohol-seeking behaviors within the VP, the GABA(A) alpha1 receptor
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