(+)-BicucullinePotent GABAA antagonist CAS# 485-49-4 |
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| Cas No. | 485-49-4 | SDF | Download SDF |
| PubChem ID | 10237 | Appearance | Yellow powder |
| Formula | C20H17NO6 | M.Wt | 367.36 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Synonyms | d-Bicuculline | ||
| Solubility | DMSO : ≥ 36 mg/mL (98.00 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one | ||
| SMILES | CN1CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3 | ||
| Standard InChIKey | IYGYMKDQCDOMRE-ZWKOTPCHSA-N | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | (+)-Bicuculline is a competitive antagonist of GABAA receptors with IC50 of 2 μM, also blocks Ca(2+)-activated potassium channels.It is effective in vitro against spore germination of some plant pathogenic fungi, it can significantly inhibit spore germination of all the fungi at concentrations of 100-1000 ppm. |
| Targets | GABA Receptor | Calcium Channel | Antifection |
| In vitro | Effect of berberine and (+/-)-bicuculline isolated from Corydalis chaerophylla on spore germination of some fungi.[Pubmed: 12058395]Folia Microbiol (Praha). 2002;47(2):161-5.
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| In vivo | The effects of adrenalectomy and gonadectomy on sex and stress-induced differences in the sensitivity of rats to bicuculline[Reference: WebLink]Exp. Brain Res., 1999, 129(3):451-6.
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| Structure Identification | Chirality Volume 1, Issue 2, pages 178–179, 1989Methiodide of the GABA antagonist (+)-bicuculline is levorotatory[Reference: WebLink]The appearance of positive charge on the nitrogen moiety of phthalideisoquinoline alkaloids brings about a strong change in the intensities of CD Cotton effects. Hence the optical rotations of enantiomeric salts and their parent base of identical configuration are often of opposite sign. Thus, the name (+)-Bicuculline-methiodide for the methiodide salt of (+)-Bicuculline is false. |
(+)-Bicuculline Dilution Calculator
(+)-Bicuculline Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7221 mL | 13.6106 mL | 27.2213 mL | 54.4425 mL | 68.0531 mL |
| 5 mM | 0.5444 mL | 2.7221 mL | 5.4443 mL | 10.8885 mL | 13.6106 mL |
| 10 mM | 0.2722 mL | 1.3611 mL | 2.7221 mL | 5.4443 mL | 6.8053 mL |
| 50 mM | 0.0544 mL | 0.2722 mL | 0.5444 mL | 1.0889 mL | 1.3611 mL |
| 100 mM | 0.0272 mL | 0.1361 mL | 0.2722 mL | 0.5444 mL | 0.6805 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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(+)-Bicuculline, a convulsant alkaloid, is the antagonist of GABA.
References:
[1]. Zahm DS, et al. Comparison of the locomotor-activating effects of bicuculline infusions into the preoptic area and ventral pallidum. Brain Struct Funct. 2014 Mar;219(2):511-26.
[2]. Johnston GA. Advantages of an antagonist: bicuculline and other GABA antagonists. Br J Pharmacol. 2013 May;169(2):328-36.
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Effect of berberine and (+/-)-bicuculline isolated from Corydalis chaerophylla on spore germination of some fungi.[Pubmed:12058395]
Folia Microbiol (Praha). 2002;47(2):161-5.
Berberine and (+/-)-bicuculline were isolated from roots and leaves, respectively, of Corydalis chaerophylla. Both were effective in vitro against spore germination of some plant pathogenic fungi (Alternaria brassicicola, A. brassicae, A. cheiranthi, A. melongenae, A. solani, Colletotrichum musae, C. falcatum, Curvularia penniseti, C. lunata, C. maculans, C. pallescens, Curvularia sp., Erysiphe pisi, E. cichoracearum, Erysiphe sp., Fusarium udum, Helminthosporium spiciferum, H. penniseti, H. frumentacei, Heterosporium sp., Oidium erysiphoides and Ustilago cynodontis). Berberine and (+/-)-bicuculline significantly inhibited spore germination of all the fungi at concentrations of 100-1000 ppm. Berberine was effective against all the fungi at all concentrations; most of the fungi did not germinate at 1000 ppm. H. penniseti conidia did not germinate at any concentration of (+/-)-bicuculline. U. cynodontis was the least sensitive fungus at lower concentrations but 800 ppm dose was highly effective.
Multiplicity of GABAA--benzodiazepine receptors.[Pubmed:2559519]
Trends Pharmacol Sci. 1989 Oct;10(10):407-11.
Binding studies suggest the presence of at least two pharmacologically distinct 'central' benzodiazepine receptors in the brain. Since central benzodiazepine receptors are allosteric modulatory sites on GABAA receptors, this evidence indirectly points to the existence of at least two GABAA receptors. Werner Sieghart describes biochemical studies that have identified several different alpha- and beta-subunits of these receptors, and molecular biological studies in which the genes encoding a variety of different alpha-, beta- and gamma-subunits have been isolated, sequenced and expressed in Xenopus oocytes. These studies all point to the existence of multiple GABAA receptors in the brain.
Intracerebral site of convulsant action of bicuculline.[Pubmed:3982215]
Life Sci. 1985 Apr 1;36(13):1295-8.
Bicuculline was injected intracerebrally in several forebrain sites of the rat. In a discrete area in the vicinity of prepiriform cortex, a single, unilateral injection of bicuculline (49 pmol) produced generalized clonic seizures documented behaviorally and electroencephalographically. This is the first identification of an anatomical site from which generalized seizures can be elicited by low doses of a chemoconvulsant.
Studies on the neuropharmacological activity of bicuculline and related compounds.[Pubmed:1247886]
Brain Res. 1976 Feb 6;102(2):283-99.
Bicuculline and 3 chemical derivatives were assayed on a variety of biological systems. Consistent with reports of studies on other animals, some of these compounds caused convulsions in insects and blocked inhibitory postsynaptic potentials in insect muscle. They all potently inhibited mouse brain acetylcholinesterase. Bicuculline and its analogs inhibited the binding of GABA in vitro to sites in crayfish muscle membranes which have properties of receptor sites; this site of action could explain the activity of bicuculline at arthropod neuromuscular junctions. These compounds, at high concentrations (over 100 muM), also inhibited GABA uptake by mouse brain homogenates at 0 degrees C apparently non-competitively. Bicucine methyl ester inhibited GABA transport by brain at 37 degrees C, consistent with non-specific membrane effects at high concentrations of drug. These and other observations cast doubt upon the specificity of bicuculline-like compounds for action on GABA synapses, especially for in vitro studies at high drug concentrations (over 10 muM). The neuroactivity of low doses of bicuculline is apparently not explained by these in vitro effects, and could very well be due to inhibition of GABA synapses at either receptor or ionophore sites. At physiological conditions of pH and temperature, bicuculline is hydrolyzed at its lactone moiety to the less active compound bicucine; this could lead to underestimates of the biological activity of bicuculline. More stable analogs studied so far are not more potent, however.
