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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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Lance R McMahon et al.
The Journal of pharmacology and experimental therapeutics, 300(2), 505-512 (2002-01-24)
Drug discrimination was used to examine the effects of benzodiazepine (BZ)(1) receptor-selective ligands in rhesus monkeys. In diazepam-treated (5.6 mg/kg, p.o.) monkeys discriminating the nonselective BZ antagonist flumazenil (0.32 mg/kg, s.c.), the BZ(1)-selective antagonist beta-carboline-3-carboxylate-t-butyl ester (beta-CCt) substituted for flumazenil.
Donna M Platt et al.
Psychopharmacology, 164(2), 151-159 (2002-10-31)
Delineation of the receptor mechanisms underlying the behavioral effects of benzodiazepines should allow for the development of drugs with improved clinical utility and reduced side effects. OBJECTIVES. The purpose of the present study was to investigate the role of GABAA/alpha1
Miroslav M Savić et al.
Pharmacology, biochemistry, and behavior, 79(2), 279-290 (2004-10-27)
Recent research using genetically modified mice has pointed to the specific contribution of individual receptor subtypes to the various effects of benzodiazepines. The aim of this study was to examine the relative significance of alpha(1)-containing GABA(A) receptors in the effects
Miroslav M Savić et al.
Psychopharmacology, 180(3), 455-465 (2005-02-19)
The pharmacological approach, using subtype selective ligands, complements genetic studies on the specific contribution of individual receptor subtypes to the various effects of benzodiazepines. The aim of this study was to examine the relative significance of alpha1-containing GABA(A) receptors in
Snjezana Lelas et al.
Psychopharmacology, 161(2), 180-188 (2002-05-01)
Conventional benzodiazepines (BZs), clinically used for treatment of anxiety and insomnia, bind to GABA(A) receptors containing alpha(1), alpha(2), alpha(3), or alpha(5) subunits. The role of these different GABA(A) receptor subtypes in mediating the subjective effects of BZs remains largely unknown.
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