Abecarnil
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MedKoo CAT#: 571354

CAS#: 111841-85-1

Description: Abecarnil is a beta carboline and a partial benzodiazepine-receptor agonist that has demonstrated promise as an anxiolytic agent. It may be useful in treating generalized anxiety disorder.


Chemical Structure

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Abecarnil
CAS# 111841-85-1

Theoretical Analysis

MedKoo Cat#: 571354
Name: Abecarnil
CAS#: 111841-85-1
Chemical Formula: C24H24N2O4
Exact Mass: 404.1736
Molecular Weight: 404.47
Elemental Analysis: C, 71.27; H, 5.98; N, 6.93; O, 15.82

Price and Availability

Size Price Availability Quantity
1.0mg USD 90.0 Ready to ship
5.0mg USD 250.0 Ready to ship
10.0mg USD 450.0 Ready to ship
25.0mg USD 950.0 Ready to ship
50.0mg USD 1650.0 Ready to ship
100.0mg USD 2950.0 Ready to ship
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Synonym: Abecarnil; ZK 112119; ZK-112119; ZK112119;

IUPAC/Chemical Name: 6-(Benzyloxy)-4-(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid 1-methylethyl ester

InChi Key: RLFKILXOLJVUNF-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C(C1=C(COC)C2=C(C=N1)NC3=C2C=C(OCC4=CC=CC=C4)C=C3)OC(C)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Abecarnil (ZK 112119) is a ligand or a partial agonist for benzodiazepine (BZ) receptor. Abecarnil can act as a positive allosteric modulator of GABAA receptor. Abecarnil inhibits the binding of the BZ [3H]lormetazepam to rat cerebral cortex membranes, with an IC50 of 0.82 nM.
In vitro activity: In vitro, abecarnil inhibited the binding of the BZ [3H]lormetazepam to rat cerebral cortex membranes with an IC50 value of 0.82 nM in comparison to 56 nM for DZP. Reference: J Pharmacol Exp Ther. 1990 Apr;253(1):334-43. https://pubmed.ncbi.nlm.nih.gov/1970361/
In vivo activity: Abecarnil, a selective benzodiazepine receptor agonist with marked anticonvulsant activity, was administered together with chronic PTZ to evaluate whether persistent activation of GABAA receptors and suppression of seizures during kindling might affect the sensitivity of septohippocampal cholinergic neurons to a challenge dose of PTZ. Abecarnil (1 mg/kg, i.p.) administered 40 min before each PTZ injection neither antagonized the decrease in basal acetylcholine release (2.26 +/- 0.19 pmol per 20-min sample) nor prevented the development of kindling. In contrast, abecarnil prevented the chronic PTZ-induced increase in the sensitivity of acetylcholine release to a challenge dose of PTZ. Reference: J Neurochem. 1997 Jan;68(1):313-8. https://pubmed.ncbi.nlm.nih.gov/8978740/

Preparing Stock Solutions

The following data is based on the product molecular weight 404.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Stephens DN, Schneider HH, Kehr W, Andrews JS, Rettig KJ, Turski L, Schmiechen R, Turner JD, Jensen LH, Petersen EN, et al. Abecarnil, a metabolically stable, anxioselective beta-carboline acting at benzodiazepine receptors. J Pharmacol Exp Ther. 1990 Apr;253(1):334-43. PMID: 1970361. 2. Serra M, Dazzi L, Cagetti E, Chessa MF, Pisu MG, Sanna A, Biggio G. Effect of pentylenetetrazole-induced kindling on acetylcholine release in the hippocampus of freely moving rats. J Neurochem. 1997 Jan;68(1):313-8. doi: 10.1046/j.1471-4159.1997.68010313.x. PMID: 8978740. 3. Barbaccia ML, Roscetti G, Bolacchi F, Concas A, Mostallino MC, Purdy RH, Biggio G. Stress-induced increase in brain neuroactive steroids: antagonism by abecarnil. Pharmacol Biochem Behav. 1996 May;54(1):205-10. doi: 10.1016/0091-3057(95)02133-7. PMID: 8728559.
In vitro protocol: 1. Stephens DN, Schneider HH, Kehr W, Andrews JS, Rettig KJ, Turski L, Schmiechen R, Turner JD, Jensen LH, Petersen EN, et al. Abecarnil, a metabolically stable, anxioselective beta-carboline acting at benzodiazepine receptors. J Pharmacol Exp Ther. 1990 Apr;253(1):334-43. PMID: 1970361.
In vivo protocol: 1. Serra M, Dazzi L, Cagetti E, Chessa MF, Pisu MG, Sanna A, Biggio G. Effect of pentylenetetrazole-induced kindling on acetylcholine release in the hippocampus of freely moving rats. J Neurochem. 1997 Jan;68(1):313-8. doi: 10.1046/j.1471-4159.1997.68010313.x. PMID: 8978740. 2. Barbaccia ML, Roscetti G, Bolacchi F, Concas A, Mostallino MC, Purdy RH, Biggio G. Stress-induced increase in brain neuroactive steroids: antagonism by abecarnil. Pharmacol Biochem Behav. 1996 May;54(1):205-10. doi: 10.1016/0091-3057(95)02133-7. PMID: 8728559.

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1: Pollack MH, Worthington JJ, Manfro GG, Otto MW, Zucker BG. Abecarnil for the treatment of generalized anxiety disorder: a placebo-controlled comparison of two dosage ranges of abecarnil and buspirone. J Clin Psychiatry. 1997;58 Suppl 11:19-23. PubMed PMID: 9363044.

2: Lydiard RB, Ballenger JC, Rickels K. A double-blind evaluation of the safety and efficacy of abecarnil, alprazolam, and placebo in outpatients with generalized anxiety disorder. Abecarnil Work Group. J Clin Psychiatry. 1997;58 Suppl 11:11-8. PubMed PMID: 9363043.

3: Turski L, Stephens DN, Jensen LH, Petersen EN, Meldrum BS, Patel S, Hansen JB, Löscher W, Schneider HH, Schmiechen R. Anticonvulsant action of the beta-carboline abecarnil: studies in rodents and baboon, Papio papio. J Pharmacol Exp Ther. 1990 Apr;253(1):344-52. PubMed PMID: 1970362.

4: Kasteleijn-Nolst Trenité DG, Groenwold RH, Schmidt B, Löscher W. Single dose efficacy evaluation of two partial benzodiazepine receptor agonists in photosensitive epilepsy patients: A placebo-controlled pilot study. Epilepsy Res. 2016 May;122:30-6. doi: 10.1016/j.eplepsyres.2016.02.003. Epub 2016 Feb 11. PubMed PMID: 26921854.

5: Rickels K, DeMartinis N, Aufdembrinke B. A double-blind, placebo-controlled trial of abecarnil and diazepam in the treatment of patients with generalized anxiety disorder. J Clin Psychopharmacol. 2000 Feb;20(1):12-8. PubMed PMID: 10653203.

6: Ozawa M, Nakada Y, Sugimachi K, Yabuuchi F, Akai T, Mizuta E, Kuno S, Yamaguchi M. Pharmacological characterization of the novel anxiolytic beta-carboline abecarnil in rodents and primates. Jpn J Pharmacol. 1994 Mar;64(3):179-87. PubMed PMID: 7912751.

7: Stephens DN, Schneider HH, Kehr W, Andrews JS, Rettig KJ, Turski L, Schmiechen R, Turner JD, Jensen LH, Petersen EN, et al. Abecarnil, a metabolically stable, anxioselective beta-carboline acting at benzodiazepine receptors. J Pharmacol Exp Ther. 1990 Apr;253(1):334-43. PubMed PMID: 1970361.

8: Aufdembrinke B. Abecarnil, a new beta-carboline, in the treatment of anxiety disorders. Br J Psychiatry Suppl. 1998;(34):55-63. PubMed PMID: 9829018.

9: Jung ME, Wallis CJ, Gatch MB, Lal H. Abecarnil and alprazolam reverse anxiety-like behaviors induced by ethanol withdrawal. Alcohol. 2000 Jun;21(2):161-8. PubMed PMID: 10963939.

10: Zanotti A, Natolino F, Contarino A, Lipartiti M, Giusti P. Abecarnil enhances recovery from diazepam tolerance. Neuropharmacology. 1999 Sep;38(9):1281-8. PubMed PMID: 10471081.

11: Natolino F, Zanotti A, Contarino A, Lipartiti M, Giusti P. Abecarnil, a beta-carboline derivative, does not exhibit anticonvulsant tolerance or withdrawal effects in mice. Naunyn Schmiedebergs Arch Pharmacol. 1996 Nov;354(5):612-7. PubMed PMID: 8938660.

12: Vorobjev VS, Sharonova IN, Skrebitsky VG, Schneider HH, Stephens DN. Abecarnil enhances GABA-induced currents in acutely isolated cerebellar Purkinje cells. Neuropharmacology. 1995 Feb;34(2):157-63. PubMed PMID: 7617141.

13: Lytle DA, Emmett-Oglesby MW, Stephens DN. Discriminative stimulus effects of midazolam and abecarnil in rats treated chronically with diazepam or abecarnil. Psychopharmacology (Berl). 1995 Oct;121(3):339-46. PubMed PMID: 8584616.

14: Anton RF, Kranzler HR, McEvoy JP, Moak DH, Bianca R. A double-blind comparison of abecarnil and diazepam in the treatment of uncomplicated alcohol withdrawal. Psychopharmacology (Berl). 1997 May;131(2):123-9. PubMed PMID: 9201799.

15: Rex A, Stephens DN, Fink H. "Anxiolytic" action of diazepam and abecarnil in a modified open field test. Pharmacol Biochem Behav. 1996 Apr;53(4):1005-11. PubMed PMID: 8801571.

16: Mumford GK, Rush CR, Griffiths RR. Abecarnil and alprazolam in humans: behavioral, subjective and reinforcing effects. J Pharmacol Exp Ther. 1995 Feb;272(2):570-80. PubMed PMID: 7853170.

17: Small GW, Bystritsky A. Double-blind, placebo-controlled trial of two doses of abecarnil for geriatric anxiety. J Clin Psychiatry. 1997;58 Suppl 11:24-9. PubMed PMID: 9363045.

18: Ozawa M, Sugimachi K, Nakada-Kometani Y, Akai T, Yamaguchi M. Chronic pharmacological activities of the novel anxiolytic beta-carboline abecarnil in rats. J Pharmacol Exp Ther. 1994 May;269(2):457-62. PubMed PMID: 7910208.

19: Sannerud CA, Ator NA, Griffiths RR. Behavioral pharmacology of abecarnil in baboons: self-injection, drug discrimination and physical dependence. Behav Pharmacol. 1992 Oct;3(5):507-516. PubMed PMID: 11224153.

20: Cooper SJ, Greenwood SE. The beta-carboline abecarnil, a novel agonist at central benzodiazepine receptors, influences saccharin and salt taste preferences in the rat. Brain Res. 1992 Dec 18;599(1):144-7. PubMed PMID: 1337300.