Title: Abecarnil
CAS Registry Number: 111841-85-1
CAS Name: 4-(Methoxymethyl)-6-(phenylmethoxy)-9H-pyrido[3,4-b]indole-3-carboxylic acid 1-methylethyl ester
Additional Names: isopropyl 6-(benzyloxy)-4-(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate; isopropyl 6-(benzyloxy)-4-(methoxymethyl)-b-carboline-3-carboxylate
Manufacturers' Codes: ZK-112119
Molecular Formula: C24H24N2O4
Molecular Weight: 404.46
Percent Composition: C 71.27%, H 5.98%, N 6.93%, O 15.82%
Literature References: Benzodiazepine receptor agonist. Prepn: H. Biere et al., DE 3609699 (1987 to Schering AG), C.A. 108, 21872z (1988). Pharmacology and receptor binding studies: D. N. Stephens et al., J. Pharmacol. Exp. Ther. 253, 334 (1990). Determn in biological samples: W. Krause et al., J. Pharm. Sci. 78, 622 (1989). Clinical pharmacokinetics: W. Krause et al., Xenobiotica 21, 763 (1991). Clinical trial in anxiety: J. C. Ballenger et al., Adv. Biochem. Psychopharmacol. 47, 431 (1992). Series of articles on pharmacology, tolerance and clinical evaluation: Psychopharmacol. Ser. 11, 50-147 (1993).
Properties: Crystals from ethyl acetate, mp 150-151°.
Melting point: mp 150-151°
Therap-Cat: Anxiolytic.
Keywords: Anxiolytic.
Status: This monograph has been retired and is no longer subject to revision or update.
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Systematic (IUPAC) name
propan-2-yl 4-(methoxymethyl)-6-(phenylmethoxy) -9H-pyrido[5,4-b]indole-3-carboxylate
Clinical data
Legal status  ?
Pharmacokinetic data
Half-life 3.4 hours (IV), 7 hours (oral)
CAS number 111841-85-1 N
ATC code None
PubChem CID 65914
ChemSpider 59323 YesY
KEGG D02594 YesY
Chemical data
Formula C24H24N2O4 
Mol. mass 404.458 g/mol
 N (what is this?)  (verify)

Abecarnil (ZK-112,119) is an anxiolytic drug from the β-Carboline family. It is one of a relatively recently developed class of medicines known as the nonbenzodiazepines, which have similar effects to the older benzodiazepine group, but with quite different chemical structures. It is a partial agonist acting selectively at the benzodiazepine site of the GABAA receptor.[1][2]

Abecarnil was originally developed as an anti-anxiety drug, but has not as yet been commercially developed for use in humans, instead so far mainly being used for research into the development of other new sedative and anxiolytic drugs. Investigations are continuing into its actions and it looks likely to be developed for use both in the treatment of anxiety,[3] and as a less addictive substitute drug for the treatment of benzodiazepine[4] and alcohol[5] addiction. Abecarnil may also have less problems of tolerance and withdrawal problems compared to nonselective full agonist benzodiazepine acting drugs.[6]

Abecarnil is a relatively subtype-selective drug which produces primarily anxiolytic effects, with comparatively less sedative or muscle relaxant properties,[7][8] and does not significantly potentiate the effects of alcohol.[9]

The abuse potential of abecarnil is thought to be less than that of benzodiazepines,[10] with only mild withdrawal symptoms noted after abrupt discontinuation of treatment.[11]