Ethyl beta-carboline-3-carboxylate (beta-CCE)An inverse agonist of benzodiazepine activity

Ethyl β-carboline-3-carboxylate (β-CCE) (CAS 74214-62-3)

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Application: An inverse agonist of benzodiazepine activity
CAS Number: 74214-62-3
Purity: ≥97%
Molecular Weight: 240.3
Molecular Formula: C14H12N2O2
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ethyl β-carboline-3-carboxylate is a polyaromatic small molecule isolable from human urine extracts, demonstrating anxiogenic effects as a partial inverse agonist of benzodiazepine activity at the GABAA receptors. β-carboline derivatives with a 3-position carbonyl functionality have demonstrated induction of convulsions and anxiogenesis comparable to the effects associated with cerebral electrolytic lesions. Ethyl β-carboline-3-carboxylate demonstrates displacement of diazepam from the benzodiazepine binding site.


References

1. Braestrup, C., et al. 1980. Proc. Natl. Acad. Sci. U.S.A. 77: 2288-2292. PMID: 6246535
2. Cain, M., et al. 1982. J. Med. Chem. 25: 1081-1091. PMID: 6127411
3. Lippke, K.P., et al. 1983. J. Med. Chem. 26: 499-503. PMID: 6300400
4. Prado de Carvalho, L.P., et al. 1983. Nature. 301: 64-66. PMID: 6296684
5. Podhorna, J., et al. 2000. Pharmacol. Biochem. Behav. 65: 267-273. PMID: 10672979
6. Dawson, G.R., et al. 2006. J. Pharmacol. Exp. Ther. 316: 1335-1345. PMID: 16326923

Physical State :
Solid
Solubility :
Soluble in DMSO, CHCL3 (10 mg/ ml), and warm ethanol (3.5 mg/ml).
Storage :
Store at room temperature
Melting Point :
228-230° C (lit.)
Boiling Point :
~470.9° C at 760 mmHg (Predicted)
Density :
~1.3 g/cm3 (Predicted)
Refractive Index :
n20D 1.70 (Predicted)
IC50 :
[3H]flunitrazepam binding to benzodiazepine receptor: IC50 = 1.4 nM (bovine); 3H]- flunitrazepam binding to GABA-A Benzodiazepine recepto: IC50 = 2 nM (rat)
Ki Data :
[3H]diazepam binding to benzodiazepine receptor: Ki= 1.1 nM
pK Values :
pKb: 5.17 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
RN7092000
PubChem CID :
105078
Merck Index :
14: 3779
MDL Number :
MFCD00009730
SMILES :
CCOC(=O)C1=NC=C2C(=C1)C3=CC=CC=C3N2

Download SDS (MSDS)

Certificate of Analysis

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