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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

SMILES

COC(=O)C1=NC=C2NC3=C(C=CC=C3)C2=C1

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
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Inverse benzodiazepine agonist beta-CCM does not reverse learning deficit induced by sleep deprivation.
2010-01-18
Effects of toluene exposure during brain growth spurt on GABA(A) receptor-mediated functions in juvenile rats.
2007-02
Chemoconvulsant-induced seizure susceptibility: toward a common genetic basis?
2007
Mouse lines selected for difference in sensitivity to beta-CCM also differ in memory processes.
2006-10-16
Anxiolytic properties of green tea polyphenol (-)-epigallocatechin gallate (EGCG).
2006-09-19
Abnormal benzodiazepine receptor function in the depressive-like behavior of diabetic mice.
2005-12
Negative GABA(A) modulators attenuate the discriminative stimulus effects of benzodiazepines and the neuroactive steroid pregnanolone in rhesus monkeys.
2005-10
Effects of ibotenic acid lesions of the mediodorsal thalamus on memory: relationship with emotional processes in mice.
2005-01-30
BetaCCM but not physostigmine enhancement of memory retrieval depends on emotional processes in mice.
2004-10
BetaCCM enhances retrieval of serial contextual but not of serial spatial memory in mice.
2004-03
Photophysical properties of methyl beta-carboline-3-carboxylate mediated by hydrogen-bonded complexes--a comparative study in different solvents.
2003-07-01
Long-lasting potentiation effects induced in rats by kindling with an inverse agonist of the benzodiazepine receptor.
2002-09
Mouse lines differing in sensitivity to beta-CCM differ in tasks used for testing antidepressants.
2002-05
Daily treatment with diazepam differentially modifies sensitivity to the effects of gamma-aminobutyric acid(A) modulators on schedule-controlled responding in rhesus monkeys.
2002-03
The negative GABA(A) modulator methyl beta-carboline-3-carboxylate attenuates the behavioral effects of the positive GABA(A) modulators triazolam and pregnanolone in rhesus monkeys.
2001-11
A pharmacological link between epilepsy and anxiety?
2001-10
The effects of flumazenil, Ro 154513 and beta-CCM on the behaviour of control and stressed mice in the staircase test.
2001-09
Form II of monoclinic methyl beta-carboline-3-carboxylate.
2001-06
Modification of the effects of benzodiazepines on the exploratory behaviors of mice on a hole-board by diabetes.
2001-05
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.
2001-04
[3H]Ro 15-1788 binding sites to brain membrane of the saltwater Mugil cephalus.
2001-03
Effects of diazepam and beta-CCM on working memory in mice: relationships with emotional reactivity.
2001-02
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.
2001-01
Two mouse lines selected for differential sensitivities to beta-carboline-induced seizures are also differentially sensitive to various pharmacological effects of other GABA(A) receptor ligands.
2000-07
Mice lacking the long splice variant of the gamma 2 subunit of the GABA(A) receptor are more sensitive to benzodiazepines.
2000-06
Patents

Sample Use Guides

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
9H-.BETA.-CARBOLINE-3-CARBOXYLIC ACID METHYL ESTER
Preferred Name English
.BETA.-CARBOLINE-3-CARBOXYLIC ACID METHYL ESTER
Systematic Name English
Code System Code Type Description
MESH
C036150
Created by admin on Wed Apr 02 10:21:52 GMT 2025 , Edited by admin on Wed Apr 02 10:21:52 GMT 2025
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PUBCHEM
107704
Created by admin on Wed Apr 02 10:21:52 GMT 2025 , Edited by admin on Wed Apr 02 10:21:52 GMT 2025
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CAS
69954-48-9
Created by admin on Wed Apr 02 10:21:52 GMT 2025 , Edited by admin on Wed Apr 02 10:21:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID40990214
Created by admin on Wed Apr 02 10:21:52 GMT 2025 , Edited by admin on Wed Apr 02 10:21:52 GMT 2025
PRIMARY
FDA UNII
I2A008F6YL
Created by admin on Wed Apr 02 10:21:52 GMT 2025 , Edited by admin on Wed Apr 02 10:21:52 GMT 2025
PRIMARY