ETHYL .BETA.-CARBOLINE-3-CARBOXYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H12N2O2
Molecular Weight	240.2573
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ETHYL .BETA.-CARBOLINE-3-CARBOXYLATE

Structure Search

SMILES

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

InChI

InChIKey=KOVRZNUMIKACTB-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C14H12N2O2
Molecular Weight	240.2573
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19179849 | https://www.ncbi.nlm.nih.gov/pubmed/23851259

Ethyl β-carboline-3-carboxylate or beta-carboline-3-carboxylic acid ethyl ester, an endogenous compound that was isolated from human urine. It is a partial inverse agonist at the benzodiazepine site on the GABA-A receptor. Experiments on rats have shown that ethyl β-carboline-3-carboxylate produces the anxiogenic-like effect but do not affect brainstem activated hippocampal theta.

Originator

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/3005790	Inverse Agonist 80

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
beta-Carbolines as benzodiazepine receptor ligands. 1. Synthesis and benzodiazepine receptor interaction of esters of beta-carboline-3-carboxylic acid.	1983 Apr	6300400
Interactions between the benzodiazepine receptor antagonist Ro 15-1788 (flumazepil) and the inverse agonist beta-CCE: behavioral studies with squirrel monkeys.	1985 Apr 8	3920465
Discriminative and aversive properties of beta-carboline-3-carboxylic acid ethyl ester, a benzodiazepine receptor inverse agonist, in rhesus monkeys.	1986 Mar 17	3005790
Anxiogenic properties of beta-CCE and FG 7142: a review of promises and pitfalls.	1988	3131790
Relative potency and effectiveness of flunitrazepam, ethanol, and beta-CCE for disrupting the acquisition and retention of response sequences in rats.	2009 Feb	19179849

Sample Use Guides

In Vivo Use Guide

in rats: 1-17.8 mg/kg. Injections for drug was administered i.p. 15 min before the start of the session or 15 min before the retention test.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:28:53 GMT 2023` Edited by `admin` on `Sat Dec 16 04:28:53 GMT 2023`
Record UNII	HYW8K5N21Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYL .BETA.-CARBOLINE-3-CARBOXYLATE

Systematic Name

English

3-CARBOETHOXY-9H-PYRIDO(3,4-B)INDOLE

Systematic Name

English

ETHYL .BETA.-CARBOLINE-3-CARBOXYLATE [MI]

Common Name

English

.BETA.-CCE

Common Name

English

ETHYL 9H-.BETA.-CARBOLINE-3-CARBOXYLATE

Systematic Name

English

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

Systematic Name

English

ETHYL 9H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLATE

Systematic Name

English

ETHYL NORHARMANCARBOXYLATE

Common Name

English

9H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID ETHYL ESTER

Systematic Name

English

NSC-610937

Code

English

NORHARMAN-3-CARBOXYLIC ACID ETHYL ESTER

Common Name

English

Code System Code Type Description

MERCK INDEX

m5104