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(+)-BICUCULLINE |
| Bicculine; D-Bicuculline; (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; (6R)-6-((5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin -5-yl)furo(3,4-e)-1,3-benzodioxol-8(6H)-one; |
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| PRODUCT IDENTIFICATION |
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CAS RN |
485-49-4 |
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EINECS RN |
207-619-7 |
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FORMULA |
C20H17NO6 |
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MOLE WEIGHT |
367.35 |
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| PHYSICAL AND CHEMICAL PROPERTIES |
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PHYSICAL STATE |
yellowish crystalline powder |
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MELTING POINT |
205 - 215 C |
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BOILING POINT |
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DENSITY |
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SOLUBILITY IN WATER |
Insoluble (soluble in chloroform 50 mg/ml, benzene, ethyl acetate, sparingly soluble in alcohol and ether). Bicuculline methiodide is a water soluble form. |
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pH |
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VAPOR DENSITY |
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REFRACTIVE INDEX |
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FLASH POINT |
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| STABILITY AND REACTIVITY | |
| STABILITY | Stable under normal conditions |
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INCOMPATIBLE MATERIALS |
Strong acids, Strong bases |
| DECOMPOSITION PRODUCTS |
Carbon oxides. Nitrogen oxides. |
| POLYMERIZATION | Has not been reported |
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NFPA RATINGS |
Health: 4, Flammability: 0, Reactivity: 0 |
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| SAFETY |
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HAZARD NOTES |
prolonged or repeated exposure can cause:, Convulsions. Target Organs: Nerves. |
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EYE |
May cause eye irritation. |
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SKIN |
Toxic if absorbed through skin.. May cause skin irritation. |
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INGESTION |
May be harmful if swallowed. |
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INHALATION |
May be harmful if inhaled. May cause respiratory tract irritation. |
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CHRONIC |
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| TRANSPORT & REGULATORY INFORMATION |
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UN NO. |
1544 |
| HAZARD CLASS |
6.1 |
| PACKING GROUP |
II |
| HAZARD CODE |
T,N |
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RISK STATEMENTS |
23/24/25-50 |
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SAFETY STATEMENTS |
36/37-45-61 |
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| EXTERNAL LINKS & GENERAL INFORMATION | ||||||||||||
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Bicuculline (Figure 1(a)) is a phthalide isoquinoline alkaloid first isolated from the plant Dicentra cucullaria and subsequently from a variety of Corydalis, Dicentra, and Adlumia species. The discovery of the GABA antagonist action of bicuculline came from a systematic study of convulsant alkaloids following the discovery of the glycine antagonist action of strychnine.Extensive studies of convulsant alkaloids showed that, whereas many isoquinoline alkaloids are convulsants, most are glycine antagonists, withGABAantagonism being restricted to the phthalide isoquinoline alkaloids that have the 1S,9R configuration (i.e., bicuculline, corlumine and (þ)-hydrastine). Bicuculline is a competitive antagonist of GABAA receptor activation. There is substantial evidence that bicuculline interacts with the same binding sites as agonists. Point mutations of a1 subunits of GABAA receptors alter both agonist and competitive antagonist properties, suggesting a close structural association of a1 Phe64 with agonist/antagonist binding sites. (http://www.usyd.edu.au/) Bicuculline (pronounced buy-kook-you-lean), which acts to counter GABA and muscimol, by elevating random nerve impulse activity. When GABA and muscimol were used, they did not improve the already good function of nerve cells in young monkeys' brains. But within two minutes, the drugs made old monkeys' visual cortex nerve cells act "young" again. Instead of various cells firing regardless of whether monkeys saw vertical, horizontal or angled bars, some cells fired only when the monkeys saw vertical bars, some fired only when horizontal bars were seen, and so on. This ability to discriminate shapes and motions wore off five to 10 minutes after the drugs were stopped. When bicuculline was used on young monkeys, their brain cells temporarily acted "old" by firing indiscriminately in response to the various bar shapes and motions. (http://www.healthcare.utah.edu/) Pharmacological actions:
Modified Bicuculline for water solubility, pH physiological stability, less active and less toxic.
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| SALES SPECIFICATION |
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APPEARANCE |
yellowish crystalline powder |
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ASSAY |
98.0% min |
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OPTICAL ROTATION |
+130 ± 1° (c = 1% in chloroform) |
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MELTING POINT |
205 - 215 C |
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| PRICE INFORMATION |
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