Bicuculline | CAS#485-49-4 | GABA-A-receptor antagonist | NMDA receptor potentiator

MedKoo Cat#: 540044 | Name: Bicuculline

Featured

Description:

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

Bicuculline is obtained from Dicentra cucullaria. It is a GABA-A-receptor antagonist and NMDA receptor potentiator used to study GABA signaling. It induces membrane depolarization and prolongs Ca- dependemtn action potentials in neurons.

Chemical Structure

Bicuculline

CAS#485-49-4 (free)

Theoretical Analysis

MedKoo Cat#: 540044

Name: Bicuculline

CAS#: 485-49-4 (free)

Chemical Formula: C20H17NO6

Exact Mass: 367.1056

Molecular Weight: 367.35

Elemental Analysis: C, 65.39; H, 4.66; N, 3.81; O, 26.13

Price and Availability

Size	Price	Availability
50mg	USD 250.00	2 Weeks
100mg	USD 450.00	2 Weeks
500mg	USD 950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

485-49-4 (free) 40709-69-1 (methiodide) 53552-05-9 (methochloride)

Synonym

Bicculine; Bicucullin; BRN 0098786; BRN0098786; BRN-0098786; NSC 32192; NSC32192; NSC-32192; (+)-Bicuculline

IUPAC/Chemical Name

(R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one

InChi Key

IYGYMKDQCDOMRE-ZWKOTPCHSA-N

InChi Code

InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1

SMILES Code

O=C1O[C@@H]([C@H]2N(C)CCC3=CC4=C(OCO4)C=C23)C5=CC=C(OCO6)C6=C51

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

(+)-Bicuculline is a light-sensitive competitive antagonist of GABA-A receptor.

In vitro activity:

The exposure to bicuculline induced long-lasting oscillatory changes in the intracellular calcium level ([Ca2+]in) of cultured non-GABAergic multipolar neurons, which were identified as mitral/tufted cells (MT cells). These MT cells exhibited the appearance of dendritic filopodia structures after a 10-min treatment with bicuculline. Reference: Eur J Neurosci. 2003 Sep;18(6):1343-52. https://pubmed.ncbi.nlm.nih.gov/14511315/

In vivo activity:

The time-course of ERSP of ASSR at 40 Hz following (+)-bicuculline treatment is summarized in Fig 2b. Two-way ANOVA revealed significant time (F(2.274, 75.04) = 4.440; P<0.05) and treatment (F(3, 33) = 8.580; P<0.01) effects. Post hoc comparisons showed significantly smaller effects in bicuculline (2 and 4 mg/kg)-treated rats than vehicle-treated rats on Dunnett’s multiple comparisons test (P<0.01). Reference: PLoS One. 2020; 15(7): e0236363. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7380603/

	Solvent	mg/mL	mM
Solubility
	DMSO	38.9	106.00
	DMF	20.0	54.44

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 367.35 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.

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. Kato-Negishi M, Muramoto K, Kawahara M, Hosoda R, Kuroda Y, Ichikawa M. Bicuculline induces synapse formation on primary cultured accessory olfactory bulb neurons. Eur J Neurosci. 2003 Sep;18(6):1343-52. doi: 10.1046/j.1460-9568.2003.02901.x. PMID: 14511315. 2. Yamazaki M, Honda S, Tamaki K, Irie M, Mihara T. Effects of (+)-bicuculline, a GABAa receptor antagonist, on auditory steady state response in free-moving rats. PLoS One. 2020 Jul 24;15(7):e0236363. doi: 10.1371/journal.pone.0236363. PMID: 32706815; PMCID: PMC7380603. 3. Malaguarnera M, Llansola M, Balzano T, Gómez-Giménez B, Antúnez-Muñoz C, Martínez-Alarcón N, Mahdinia R, Felipo V. Bicuculline Reduces Neuroinflammation in Hippocampus and Improves Spatial Learning and Anxiety in Hyperammonemic Rats. Role of Glutamate Receptors. Front Pharmacol. 2019 Feb 25;10:132. doi: 10.3389/fphar.2019.00132. PMID: 30858801; PMCID: PMC6397886.

In vitro protocol:

In vivo protocol:

1. Yamazaki M, Honda S, Tamaki K, Irie M, Mihara T. Effects of (+)-bicuculline, a GABAa receptor antagonist, on auditory steady state response in free-moving rats. PLoS One. 2020 Jul 24;15(7):e0236363. doi: 10.1371/journal.pone.0236363. PMID: 32706815; PMCID: PMC7380603. 2. Malaguarnera M, Llansola M, Balzano T, Gómez-Giménez B, Antúnez-Muñoz C, Martínez-Alarcón N, Mahdinia R, Felipo V. Bicuculline Reduces Neuroinflammation in Hippocampus and Improves Spatial Learning and Anxiety in Hyperammonemic Rats. Role of Glutamate Receptors. Front Pharmacol. 2019 Feb 25;10:132. doi: 10.3389/fphar.2019.00132. PMID: 30858801; PMCID: PMC6397886.

1: Ma J, Lin C, Wen C, Xiang Z, Yang X, Wang X. Determination of bicuculline in rat plasma by liquid chromatography mass spectrometry and its application in a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Mar 15;953-954:143-6. doi: 10.1016/j.jchromb.2014.02.006. Epub 2014 Feb 18. PubMed PMID: 24607696. 2: Ramerstorfer J, Foppa V, Thiery H, Hermange P, Janody S, Berger ML, Dodd RH, Sieghart W. GABA(A) receptor subtype-selectivity of novel bicuculline derivatives. Curr Med Chem. 2015;22(6):771-80. PubMed PMID: 25386826. 3: Ionov ID, Roslavtseva LA. Coadministration of bicuculline and NMDA induces paraplegia in the rat. Brain Res. 2012 Apr 27;1451:27-33. doi: 10.1016/j.brainres.2012.03.015. Epub 2012 Mar 13. PubMed PMID: 22445063. 4: Srivastava A, Tandon P, Jain S, Asthana BP. Antagonistic properties of a natural product-Bicuculline with the gamma-aminobutyric acid receptor: studied through electrostatic potential mapping, electronic and vibrational spectra using ab initio and density functional theory. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Dec 15;84(1):144-55. doi: 10.1016/j.saa.2011.09.022. Epub 2011 Sep 16. PubMed PMID: 21968210. 5: Covelo IR, Patel ZI, Luviano JA, Stratford TR, Wirtshafter D. Manipulation of GABA in the ventral pallidum, but not the nucleus accumbens, induces intense, preferential, fat consumption in rats. Behav Brain Res. 2014 Aug 15;270:316-25. doi: 10.1016/j.bbr.2014.05.032. Epub 2014 May 24. PubMed PMID: 24867334. 6: Lavezzi HN, Parsley KP, Zahm DS. Modulation of locomotor activation by the rostromedial tegmental nucleus. Neuropsychopharmacology. 2015 Feb;40(3):676-87. doi: 10.1038/npp.2014.223. Epub 2014 Aug 28. PubMed PMID: 25164249; PubMed Central PMCID: PMC4289956. 7: Rysakova MP, Pavlova IV. [Behavior of high- and low-anxiety rats after modulation of GABAergic transmission in basolateral amygdala]. Ross Fiziol Zh Im I M Sechenova. 2014 Jun;100(6):736-49. Russian. PubMed PMID: 25665398. 8: Hasanein P, Sharifi M. GABA(A) receptors in the central amygdala are involved in memory retention deficits induced by cannabinoids in rats. Pharmacol Biochem Behav. 2015 Nov;138:26-31. doi: 10.1016/j.pbb.2015.09.010. Epub 2015 Sep 12. PubMed PMID: 26368844. 9: Druzin M, Haage D, Johansson S. Bicuculline free base blocks voltage-activated K+ currents in rat medial preoptic neurons. Neuropharmacology. 2004 Feb;46(2):285-95. PubMed PMID: 14680766. 10: Olsen RW, Ban M, Miller T. Studies on the neuropharmacological activity of bicuculline and related compounds. Brain Res. 1976 Feb 6;102(2):283-99. PubMed PMID: 1247886. 11: Schmoutz CD, Guerin GF, Goeders NE. Role of GABA-active neurosteroids in the efficacy of metyrapone against cocaine addiction. Behav Brain Res. 2014 Sep 1;271:269-76. doi: 10.1016/j.bbr.2014.06.032. Epub 2014 Jun 21. PubMed PMID: 24959859. 12: Voisin DL, Herbison AE, Poulain DA. Central inhibitory effects of muscimol and bicuculline on the milk ejection reflex in the anaesthetized rat. J Physiol. 1995 Feb 15;483 ( Pt 1):211-24. Erratum in: J Physiol (Lond) 1995 Jun 15;485(Pt 3):873. PubMed PMID: 7776233; PubMed Central PMCID: PMC1157883. 13: Karson AB, Aker R, Ateş N, Onat F. Cardiovascular effects of intracerebroventricular bicuculline in rats with absence seizures. Epilepsy Res. 1999 Apr;34(2-3):231-9. PubMed PMID: 10210038. 14: Cantafora E, Giorgi FS, Frenzilli G, Scarcelli V, Busceti CL, Nigro M, Bernardeschi M, Fornai F. Region-specific DNA alterations in focally induced seizures. J Neural Transm (Vienna). 2014 Nov;121(11):1399-403. doi: 10.1007/s00702-014-1211-5. Epub 2014 Apr 20. PubMed PMID: 24748548. 15: Dickinson-Anson H, Mesches MH, Coleman K, McGaugh JL. Bicuculline administered into the amygdala blocks benzodiazepine-induced amnesia. Behav Neural Biol. 1993 Jul;60(1):1-4. PubMed PMID: 8216155. 16: Mori N, Watanabe M. Comparison of effects of bilateral injections of bicuculline and muscimol into the caudate-putamen of amygdaloid-kindled rats. Neurosci Lett. 1994 Mar 14;169(1-2):129-32. PubMed PMID: 8047267. 17: Pericić D, Bujas M, Mirković K, Jazvinsćak M. Effects of adrenalectomy and gonadectomy on sex and stress-induced differences in bicuculline-induced convulsions. Exp Brain Res. 1999 Dec;129(3):451-6. PubMed PMID: 10591916. 18: Kalappa BI, Uteshev VV. The dual effect of PNU-120596 on α7 nicotinic acetylcholine receptor channels. Eur J Pharmacol. 2013 Oct 15;718(1-3):226-34. doi: 10.1016/j.ejphar.2013.08.027. Epub 2013 Sep 11. PubMed PMID: 24036349; PubMed Central PMCID: PMC3839061. 19: Hsu DZ, Liu MY. Bicuculline methiodide attenuates hepatic injury and decreases mortality in septic rats: role of cytokines. Shock. 2004 Oct;22(4):347-50. PubMed PMID: 15377890. 20: Johansson S, Druzin M, Haage D, Wang MD. The functional role of a bicuculline-sensitive Ca2+-activated K+ current in rat medial preoptic neurons. J Physiol. 2001 May 1;532(Pt 3):625-35. PubMed PMID: 11313434; PubMed Central PMCID: PMC2278573.