Abecarnil

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571354

CAS#: 644-48-4

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.


Price and Availability

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Abecarnil is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571354
Name: Abecarnil
CAS#: 644-48-4
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


Synonym: Abecarnil

IUPAC/Chemical Name: 9H-Pyrido(3,4-b)indole-3-carboxylic acid, 1-(methoxymethyl)-6-(phenylmethoxy)-, 1-methylethyl ester

InChi Key: SJFZRWRLNCHBJF-UHFFFAOYSA-N

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

SMILES Code: O=C(C1=CC2=C(C(COC)=N1)NC3=C2C=C(OCC4=CC=CC=C4)C=C3)OC(C)C


Technical Data

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).

Harmonized System Code:
293490


References

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.