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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=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
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
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 Jul
Mice lacking the long splice variant of the gamma 2 subunit of the GABA(A) receptor are more sensitive to benzodiazepines.
2000 Jun
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
Effects of diazepam and beta-CCM on working memory in mice: relationships with emotional reactivity.
2001 Feb
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.
2001 Jan
Form II of monoclinic methyl beta-carboline-3-carboxylate.
2001 Jun
[3H]Ro 15-1788 binding sites to brain membrane of the saltwater Mugil cephalus.
2001 Mar
Modification of the effects of benzodiazepines on the exploratory behaviors of mice on a hole-board by diabetes.
2001 May
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 Nov
A pharmacological link between epilepsy and anxiety?
2001 Oct
The effects of flumazenil, Ro 154513 and beta-CCM on the behaviour of control and stressed mice in the staircase test.
2001 Sep
Daily treatment with diazepam differentially modifies sensitivity to the effects of gamma-aminobutyric acid(A) modulators on schedule-controlled responding in rhesus monkeys.
2002 Mar
Mouse lines differing in sensitivity to beta-CCM differ in tasks used for testing antidepressants.
2002 May
Long-lasting potentiation effects induced in rats by kindling with an inverse agonist of the benzodiazepine receptor.
2002 Sep
Photophysical properties of methyl beta-carboline-3-carboxylate mediated by hydrogen-bonded complexes--a comparative study in different solvents.
2003 Jul 1
BetaCCM enhances retrieval of serial contextual but not of serial spatial memory in mice.
2004 Mar
BetaCCM but not physostigmine enhancement of memory retrieval depends on emotional processes in mice.
2004 Oct
Abnormal benzodiazepine receptor function in the depressive-like behavior of diabetic mice.
2005 Dec
Effects of ibotenic acid lesions of the mediodorsal thalamus on memory: relationship with emotional processes in mice.
2005 Jan 30
Negative GABA(A) modulators attenuate the discriminative stimulus effects of benzodiazepines and the neuroactive steroid pregnanolone in rhesus monkeys.
2005 Oct
Mouse lines selected for difference in sensitivity to beta-CCM also differ in memory processes.
2006 Oct 16
Anxiolytic properties of green tea polyphenol (-)-epigallocatechin gallate (EGCG).
2006 Sep 19
Chemoconvulsant-induced seizure susceptibility: toward a common genetic basis?
2007
Effects of toluene exposure during brain growth spurt on GABA(A) receptor-mediated functions in juvenile rats.
2007 Feb
Inverse benzodiazepine agonist beta-CCM does not reverse learning deficit induced by sleep deprivation.
2010 Jan 18
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
.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
Created by admin on Sat Dec 16 18:10:33 GMT 2023 , Edited by admin on Sat Dec 16 18:10:33 GMT 2023
PRIMARY
PUBCHEM
107704
Created by admin on Sat Dec 16 18:10:33 GMT 2023 , Edited by admin on Sat Dec 16 18:10:33 GMT 2023
PRIMARY
CAS
69954-48-9
Created by admin on Sat Dec 16 18:10:33 GMT 2023 , Edited by admin on Sat Dec 16 18:10:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID40990214
Created by admin on Sat Dec 16 18:10:33 GMT 2023 , Edited by admin on Sat Dec 16 18:10:33 GMT 2023
PRIMARY
FDA UNII
I2A008F6YL
Created by admin on Sat Dec 16 18:10:33 GMT 2023 , Edited by admin on Sat Dec 16 18:10:33 GMT 2023
PRIMARY