MedKoo Cat#: 561192 | Name: Bicuculline methiodide
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Description:

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

Bicuculline methiodide is a GABA(A) receptor antagonist. Bicuculline methiodide attenuates inflammation by inhibiting the production of proinflammatory cytokines, such as tumor necrosis factor-alpha, and by increasing the production of the anti-inflammatory cytokine interleukin-10, both of which play important roles in the pathogenesis of sepsis.

Chemical Structure

Bicuculline methiodide
Bicuculline methiodide
CAS#40709-69-1 (methiodide)

Theoretical Analysis

MedKoo Cat#: 561192

Name: Bicuculline methiodide

CAS#: 40709-69-1 (methiodide)

Chemical Formula: C21H20INO6

Exact Mass: 0.0000

Molecular Weight: 509.30

Elemental Analysis: C, 49.53; H, 3.96; I, 24.92; N, 2.75; O, 18.85

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 650.00 2 Weeks
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Synonym
Bicuculline methiodide
IUPAC/Chemical Name
(S)-6,6-dimethyl-5-((R)-8-oxo-6,8-dihydro-[1,3]dioxolo[4,5-e]isobenzofuran-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide
InChi Key
HKJKCPKPSSVUHY-GRTNUQQKSA-M
InChi Code
InChI=1S/C21H20NO6.HI/c1-22(2)6-5-11-7-15-16(26-9-25-15)8-13(11)18(22)19-12-3-4-14-20(27-10-24-14)17(12)21(23)28-19;/h3-4,7-8,18-19H,5-6,9-10H2,1-2H3;1H/q+1;/p-1/t18-,19+;/m0./s1
SMILES Code
C[N+]1(C)[C@H]([C@@H]2OC(C3=C4OCOC4=CC=C32)=O)C5=CC(OCO6)=C6C=C5CC1.[I-]
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

Preparing Stock Solutions

The following data is based on the product molecular weight 509.30 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
1: Remler MP, Marcussen WH. Bicuculline methiodide in the blood-brain barrier-epileptogen model of epilepsy. Epilepsia. 1985 Jan-Feb;26(1):69-73. PubMed PMID: 3971950. 2: Barolet AW, Li A, Liske S, Morris ME. Antagonist actions of bicuculline methiodide and picrotoxin on extrasynaptic gamma-aminobutyric acid receptors. Can J Physiol Pharmacol. 1985 Nov;63(11):1465-70. PubMed PMID: 3000559. 3: Ueda H, Ge M, Satoh M, Takagi H. Subconvulsive doses of intracisternal bicuculline methiodide, a GABAA receptor antagonist, produce potent analgesia as measured in the tail pinch test in mice. Eur J Pharmacol. 1987 Apr 7;136(1):129-31. PubMed PMID: 3036541. 4: Maksay G. Differential effects of thiocyanate on the binding thermodynamics of bicuculline methiodide versus SR95531 (gabazine) to the gamma-aminobutyric acid receptor-ionophore complex. Biochem Pharmacol. 1998 Sep 15;56(6):729-31. PubMed PMID: 9751077. 5: Uemura S, Kimura H. Amygdaloid kindling with bicuculline methiodide in rats. Exp Neurol. 1988 Dec;102(3):346-53. PubMed PMID: 3197791. 6: Di Scala G, Schmitt P, Karli P. Flight induced by infusion of bicuculline methiodide into periventricular structures. Brain Res. 1984 Sep 10;309(2):199-208. PubMed PMID: 6478218. 7: Gruenthal M, Armstrong DR, Ault B, Nadler JV. Comparison of seizures and brain lesions produced by intracerebroventricular kainic acid and bicuculline methiodide. Exp Neurol. 1986 Sep;93(3):621-30. PubMed PMID: 3743707. 8: Turski L, Diedrichs S, Klockgether T, Schwarz M, Turski WA, Sontag KH, Bortolotto ZA, Calderazzo-Filho LS, Cavalheiro EA. Paradoxical anticonvulsant activity of the gamma-aminobutyrate antagonist bicuculline methiodide in the rat striatum. Synapse. 1991 Jan;7(1):14-20. PubMed PMID: 2006466. 9: Hsu DZ, Liu MY. Effect of GABA(A) receptor antagonist bicuculline methiodide on hypotension in endotoxin-intoxicated rats. Toxicology. 2004 Aug 5;200(2-3):213-9. PubMed PMID: 15212817. 10: Cavalheiro EA, Bortolotto ZA, Turski L. Microinjections of the gamma-aminobutyrate antagonist, bicuculline methiodide, into the caudate-putamen prevent amygdala-kindled seizures in rats. Brain Res. 1987 May 19;411(2):370-2. PubMed PMID: 3607440. 11: 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. 12: Johnson SW, Seutin V. Bicuculline methiodide potentiates NMDA-dependent burst firing in rat dopamine neurons by blocking apamin-sensitive Ca2+-activated K+ currents. Neurosci Lett. 1997 Aug 1;231(1):13-6. PubMed PMID: 9280156. 13: Kyriazi HT, Carvell GE, Brumberg JC, Simons DJ. Quantitative effects of GABA and bicuculline methiodide on receptive field properties of neurons in real and simulated whisker barrels. J Neurophysiol. 1996 Feb;75(2):547-60. PubMed PMID: 8714634. 14: Franklin PH, Zhang G, Tripp ED, Murray TF. Adenosine A1 receptor activation mediates suppression of (-) bicuculline methiodide-induced seizures in rat prepiriform cortex. J Pharmacol Exp Ther. 1989 Dec;251(3):1229-36. PubMed PMID: 2600813. 15: Mares P, Chino M, Kubová H, Mathern P, Veliký M. Convulsant action of systemically administered glutamate and bicuculline methiodide in immature rats. Epilepsy Res. 2000 Dec;42(2-3):183-9. PubMed PMID: 11074190. 16: Jones MS, Barth DS. Effects of bicuculline methiodide on fast (>200 Hz) electrical oscillations in rat somatosensory cortex. J Neurophysiol. 2002 Aug;88(2):1016-25. PubMed PMID: 12163550. 17: Weng X, Rosenberg HC. Infusion of bicuculline methiodide into the tectum: model specificity of pro- and anticonvulsant actions. Epilepsy Res. 1992 Jun;12(1):1-8. PubMed PMID: 1526225. 18: Nonogaki K, Iguchi A, Sakamoto N. Bicuculline methiodide influences the central nervous system to produce hyperglycemia in rats. J Neuroendocrinol. 1994 Aug;6(4):443-6. PubMed PMID: 7987375. 19: Maksay G, Ticku MK. Kinetic differences in GABA receptor binding following GABA and bicuculline methiodide pretreatment. Neurosci Lett. 1984 Oct 12;51(2):219-24. PubMed PMID: 6096774. 20: Hwa GG, Avoli M. Cesium potentiates epileptiform activities induced by bicuculline methiodide in rat neocortex maintained in vitro. Epilepsia. 1991 Nov-Dec;32(6):747-54. PubMed PMID: 1683833.