.BETA.-CARBOLINE-3-CARBOXYLIC ACID METHYL ESTER

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H10N2O2
Molecular Weight	226.2307
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of .BETA.-CARBOLINE-3-CARBOXYLIC ACID METHYL ESTER

Structure Search

SMILES

COC(=O)C1=CC2=C(NC3=CC=CC=C23)C=N1

InChI

InChIKey=UKHFPVCOXBJPIN-UHFFFAOYSA-N

InChI=1S/C13H10N2O2/c1-17-13(16)11-6-9-8-4-2-3-5-10(8)15-12(9)7-14-11/h2-7,15H,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6300400 | https://www.ncbi.nlm.nih.gov/pubmed/19962429

Methyl beta-carboline-3-carboxylate (beta-CCM or beta-carboline-3 carboxylic acid methyl ester) is an inverse agonist of benzodiazepine site of GABA-A receptor. Experiments on rats have shown that beta-CCM does not reverse learning deficit induced by sleep deprivation.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6300400	Inverse Agonist 80

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Identification of amino acid residues responsible for the alpha5 subunit binding selectivity of L-655,708, a benzodiazepine binding site ligand at the GABA(A) receptor.	2001 Apr	11299307
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.	2001 Jan	11145985
Form II of monoclinic methyl beta-carboline-3-carboxylate.	2001 Jun	11408687
Mouse lines differing in sensitivity to beta-CCM differ in tasks used for testing antidepressants.	2002 May	11900813
Photophysical properties of methyl beta-carboline-3-carboxylate mediated by hydrogen-bonded complexes--a comparative study in different solvents.	2003 Jul 1	12914912
BetaCCM enhances retrieval of serial contextual but not of serial spatial memory in mice.	2004 Mar	15096912
Abnormal benzodiazepine receptor function in the depressive-like behavior of diabetic mice.	2005 Dec	16325247
Negative GABA(A) modulators attenuate the discriminative stimulus effects of benzodiazepines and the neuroactive steroid pregnanolone in rhesus monkeys.	2005 Oct	15983789
Anxiolytic properties of green tea polyphenol (-)-epigallocatechin gallate (EGCG).	2006 Sep 19	16859659

Patents

Sample Use Guides

In Vivo Use Guide

Male Wistar rats: were treated with saline or 0.5mg/kg beta-CCM (Methyl β-carboline-3-carboxylat) before passive avoidance training (AD), and were tested 30 min or 24h later. beta-CCM increased passive avoidance (PA) performance in control animals in both short and long term retention tests, whereas SD and SR animals were unaffected by the drug treatment.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

.BETA.-CARBOLINE-3-CARBOXYLIC ACID METHYL ESTER

Systematic Name

English

9H-.BETA.-CARBOLINE-3-CARBOXYLIC ACID METHYL ESTER

Systematic Name

English

Code System Code Type Description

MESH

C036150