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E001

Sigma-Aldrich

Ethyl β-carboline-3-carboxylate

solid

Synonym(s):

β-CCE, Ethyl 9H-pyrido[3,4-b]indole-3-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C14H12N2O2
CAS Number:
74214-62-3
Molecular Weight:
240.26
MDL number:
MFCD00009730
UNSPSC Code:
12352103

form

solid

mp

228-230 °C (lit.)

solubility

ethanol: 3.5 mg/mL (warm)
DMSO: soluble

SMILES string

CCOC(=O)c1cc2c(cn1)[nH]c3ccccc23

InChI

1S/C14H12N2O2/c1-2-18-14(17)12-7-10-9-5-3-4-6-11(9)16-13(10)8-15-12/h3-8,16H,2H2,1H3

InChI key

KOVRZNUMIKACTB-UHFFFAOYSA-N

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Biochem/physiol Actions

Benzodiazepine inverse agonist which may be closely related to the endogenous ligand for the benzodiazepine receptor in brain.

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Product No.
Description
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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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P Skolnick et al.
Psychopathology, 17 Suppl 1, 25-36 (1984-01-01)
The ethyl ester of beta-carboline-3-carboxylic acid (beta-CCE) has a high affinity for benzodiazepine receptors and can antagonize some of the pharmacologic actions of benzodiazepines in rodents. Administration of beta-CCE (2.5 mg/kg) to chair-adapted, male rhesus monkeys (7-9 kg) elicited a
P J Cowen et al.
Nature, 290(5801), 54-55 (1981-03-05)
The mammalian central nervous system possesses specific high-affinity binding sites for the benzodiazepines and considerable evidence suggests that these binding sites are the pharmacological receptors through which these compounds act. Recently, ethyl beta-carboline-3-carboxylate (beta-CCE) has been identified in both human
C Braestrup et al.
Science (New York, N.Y.), 216(4551), 1241-1243 (1982-06-11)
The gamma-aminobutyric acid (GABA)-benzodiazepine receptor complex, which is composed of distinct proteins embedded in the neuronal plasma membrane, is important for several effects of benzodiazepines, including protection afforded against convulsions. During structural modification of ethyl beta-carboline-3-carboxylate an agent was discovered

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