ABECARNIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H24N2O4
Molecular Weight	404.4584
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COCC1=C(N=CC2=C1C3=C(N2)C=CC(OCC4=CC=CC=C4)=C3)C(=O)OC(C)C

InChI

InChIKey=RLFKILXOLJVUNF-UHFFFAOYSA-N

InChI=1S/C24H24N2O4/c1-15(2)30-24(27)23-19(14-28-3)22-18-11-17(29-13-16-7-5-4-6-8-16)9-10-20(18)26-21(22)12-25-23/h4-12,15,26H,13-14H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C24H24N2O4
Molecular Weight	404.4584
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/1970361 | https://www.ncbi.nlm.nih.gov/pubmed/7908435 | https://www.ncbi.nlm.nih.gov/pubmed/9829018 | https://adisinsight.springer.com/drugs/800000651

Abecarnil (isopropyl 6-benzyloxy-4-methoxymethyl-beta-carboline-3-carboxylate) is a nonselective mixed full agonist/partial agonist at GABA(A) receptor subtypes. Abecarnil possesses anxiolytic and anticonvulsant properties. Abecarnil has been studied in the treatment of anxiety disorders however its development has been discontinued.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes.	2010-06-25	20303942
Acute neuropsychological effects of MDMA and ethanol (co-)administration in healthy volunteers.	2008-04	18305926
Generalised anxiety disorder.	2007-11-20	19450347
Neuroprotective effects of the beta-carboline abecarnil studied in cultured cortical neurons and organotypic retinal cultures.	2007-06	17449066
Anticipation and consumption of food each increase the concentration of neuroactive steroids in rat brain and plasma.	2006-09	16938341
Role of brain neuroactive steroids in the functional interplay between the GABA(A) and the NPY-Y1 receptor mediated signals in the amygdala.	2006-08	16824587
Generalised anxiety disorder.	2005-12	16620453
Abecarnil and palatability: taste reactivity in normal ingestion in male rats.	2005-07	15935458
The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics.	2005-05	15926867
Anxioselective anxiolytics: can less be more?	2004-10-01	15464051
Generalised anxiety disorder.	2004-06	15652060
Neuroanatomical and pharmacological evidence for a functional interaction between GABAergic and NPY-Y1 transmission in the amygdala of Y1R/LacZ transgenic mice.	2004	15581397
Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site.	2003-08	12871032
Generalised anxiety disorder.	2003-06	12967407
Treating generalised anxiety disorder.	2003-03-29	12663409
Discriminative stimulus effects of positive GABAA modulators and other anxiolytics, sedatives, and anticonvulsants in untreated and diazepam-treated monkeys.	2003-01	12490581
Synthesis of beta- and gamma-carbolines by the palladium-catalyzed iminoannulation of alkynes.	2002-12-27	12492334
5-ethoxymethyl-7-fluoro-3-oxo-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2a]pyridine-4-N-(2-fluorophenyl)carboxamide (RWJ-51204), a new nonbenzodiazepine anxiolytic.	2002-11	12388665
Psychopharmacology of anxiety disorders.	2002-09	22033867
Functional pharmacology of GABA(A) receptors containing the chicken brain gamma 4 subunit.	2001-05-04	11348623
Use of negatively reinforcing electrical brain stimulation to detect conventional and nonconventional anxiolytics as well as an anxiogenic drug.	2001-01	11274705
Abecarnil, a beta-carboline derivative, does not exhibit anticonvulsant tolerance or withdrawal effects in mice.	1996-11	8938660
Antagonism of isoniazid-induced convulsions by abecarnil in mice tolerant to diazepam.	1995-10	8577786
Pharmacology of gamma-aminobutyric acidA receptor complex after the in vivo administration of the anxioselective and anticonvulsant beta-carboline derivative abecarnil.	1992-12	1361574
Anticonvulsant action of the beta-carboline abecarnil: studies in rodents and baboon, Papio papio.	1990-04	1970362

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:31 GMT 2025`
Record UNII	IZM1PNJ3JL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZK-112119

Preferred Name

English

ABECARNIL

Official Name

English

ABECARNIL [MI]

Common Name

English

Abecarnil [WHO-DD]

Common Name

English

ABECARNIL [MART.]

Common Name

English

abecarnil [INN]

Common Name

English

ISOPROPYL 6-(BENZYLOXY)-4-(METHOXYMETHYL)-9H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLATE

Systematic Name

English

9H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, 4-(METHOXYMETHYL)-6-(PHENYLMETHOXY)-, 1-METHYLETHYL ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197