CAS No.485-49-4,(+)-Bicuculline Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	485-49-4
Name:	(+)-Bicuculline
Article Data:	5

Formula:	C₂₀H₁₇NO₆
Molecular Weight:	367.358
Synonyms:	Bicuculline(6CI,7CI,8CI);Furo[3,4-e]-1,3-benzodioxol-8(6H)-one,6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-,[R-(R,S)]-;Bicucullin;Bucuculline;NSC 32192;d-Bicuculline;
EINECS:	207-619-7
Density:	1.473 g/cm³
Melting Point:	193-197 °C
Boiling Point:	542.3 °C at 760 mmHg
Flash Point:	281.8 °C
Appearance:	pale yellow solid
Hazard Symbols:	T, N, Xn
Risk Codes:	23/24/25-50-36/37/38-20/21/22
Safety:	36/37-45-61-36-26
Transport Information:	UN 1544 6.1/PG 2
PSA:	66.46000
LogP:	2.52260

Synthetic route

: 50-00-0
formaldehyd

: 185022-39-3
(+)-Norbicuculline

: 485-49-4
bicuculline

Conditions

Conditions	Yield
With formic acid at 100℃; for 0.25h;	81%

: 56083-00-2
(+/-)-bicuculline

: 485-49-4
bicuculline

Conditions

Conditions	Yield
With L-(-)-tartaric acid

(-)-bicucine: (-)-bicucine

: 485-49-4
bicuculline

Conditions

Conditions	Yield
With hydrogenchloride

: 64395-07-9
8-oxo-6,8-dihydro-[1,3]dioxolo[4,5-e]isobenzofuran-6-carboxylic acid

: 485-49-4
bicuculline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: thionyl chloride / benzene / 2 h / Heating 2: aq. NaOH / benzene / 1 h 3: 76 percent / POCl3 / 1 h / 100 °C 4: NaBH4, AcOH / CH2Cl2 / 4 h / 0 - 5 °C 5: 81 percent / HCOOH / 0.25 h / 100 °C View Scheme

: 58343-48-9
5-formyl-benzo[1,3]dioxole-4-carboxylic acid

: 485-49-4
bicuculline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1) HCl, 2) H2SO4 / 1) H2O, 0-5 deg C, 5 h, 2) H2O, reflux, 2 h 2: thionyl chloride / benzene / 2 h / Heating 3: aq. NaOH / benzene / 1 h 4: 76 percent / POCl3 / 1 h / 100 °C 5: NaBH4, AcOH / CH2Cl2 / 4 h / 0 - 5 °C 6: 81 percent / HCOOH / 0.25 h / 100 °C View Scheme

: 1026278-40-9
8-Oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxole-6-carbonyl chloride

: 485-49-4
bicuculline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. NaOH / benzene / 1 h 2: 76 percent / POCl3 / 1 h / 100 °C 3: NaBH4, AcOH / CH2Cl2 / 4 h / 0 - 5 °C 4: 81 percent / HCOOH / 0.25 h / 100 °C View Scheme

: 185022-35-9
8-Oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxole-6-carboxylic acid (2-benzo[1,3]dioxol-5-yl-ethyl)-amide

: 485-49-4
bicuculline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / POCl3 / 1 h / 100 °C 2: NaBH4, AcOH / CH2Cl2 / 4 h / 0 - 5 °C 3: 81 percent / HCOOH / 0.25 h / 100 °C View Scheme

: 6-[7,8-Dihydro-6H-[1,3]dioxolo[4,5-g]isoquinolin-(5E)-ylidene]-6H-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-8-one; hydrochloride

: 485-49-4
bicuculline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4, AcOH / CH2Cl2 / 4 h / 0 - 5 °C 2: 81 percent / HCOOH / 0.25 h / 100 °C View Scheme

: 74-88-4
methyl iodide

: 485-49-4
bicuculline

: 40709-69-1, 55950-07-7, 59614-39-0
bicuculline methiodide

Conditions

Conditions	Yield
In chloroform for 45h; Ambient temperature;	100%

: 1005-56-7
phenylcarbonochloridothioate

: 485-49-4
bicuculline

: (2-{6-[Chloro-(8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-methyl]-benzo[1,3]dioxol-5-yl}-ethyl)-methyl-thiocarbamic acid O-phenyl ester

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	87%

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History

BICUCULLINE(485-49-4) was first identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.

Specification

The Bicuculline is an organic compound with the formula C₂₀H₁₇NO₆. The IUPAC name of this chemical is (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. With the CAS registry number 485-49-4, it is also named as Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (6R)-. The product's categories are Alkaloids; Intermediates & Fine Chemicals; Pharmaceuticals; GABA/Glycine Receptor; GABA. Besides, it is a pale yellow solid, which should be stored in a closed and dry place at temperature of 4 °C. It is a light-sensitive competitive antagonist of GABAA receptors.

Physical properties about Bicuculline are: (1)ACD/LogP: 2.88; (2)ACD/LogD (pH 5.5): 1.65; (3)ACD/LogD (pH 7.4): 2.8; (4)ACD/BCF (pH 5.5): 5.33; (5)ACD/BCF (pH 7.4): 75.74; (6)ACD/KOC (pH 5.5): 51.4; (7)ACD/KOC (pH 7.4): 730.67; (8)#H bond acceptors: 7; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 66.46 Å²; (11)Index of Refraction: 1.665; (12)Molar Refractivity: 92.61 cm³; (13)Molar Volume: 249.3 cm³; (14)Polarizability: 36.71×10^-24cm³; (15)Surface Tension: 61.5 dyne/cm; (16)Density: 1.473 g/cm³; (17)Flash Point: 281.8 °C; (18)Enthalpy of Vaporization: 82.04 kJ/mol; (19)Boiling Point: 542.3 °C at 760 mmHg; (20)Vapour Pressure: 7.98E-12 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is harmful and toxic by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin and very toxic to aquatic organisms. When you are using it, wear suitable protective clothing and gloves. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1O[C@H](c3c1c2OCOc2cc3)[C@@H]5c4cc6OCOc6cc4CCN5C
(2)InChI: InChI=1/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
(3)InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHBP
(4)Std. InChI: 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
(5)Std. InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	8480ug/kg (8.48mg/kg)		Current Toxicology. Vol. 1, Pg. 199, 1993.