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(+)-Bicuculline
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Name

(+)-Bicuculline

 EINECS 207-619-7
CAS No. 485-49-4 Density 1.473 g/cm3
PSA 66.46000 LogP 2.52260
Solubility N/A Melting Point 193-197 °C
Formula C20H17NO6 Boiling Point 542.3 °C at 760 mmHg
Molecular Weight 367.358 Flash Point 281.8 °C
Transport Information UN 1544 6.1/PG 2 Appearance pale yellow solid
Safety 36/37-45-61-36-26 Risk Codes 23/24/25-50-36/37/38-20/21/22
Molecular Structure Molecular Structure of 485-49-4 ((+)-Bicuculline) Hazard Symbols ToxicT, DangerousN, HarmfulXn
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;

Article Data 5

(+)-Bicuculline Synthetic route

50-00-0

formaldehyd

185022-39-3

(+)-Norbicuculline

485-49-4

bicuculline

Conditions
ConditionsYield
With formic acid at 100℃; for 0.25h;81%
56083-00-2

(+/-)-bicuculline

485-49-4

bicuculline

Conditions
ConditionsYield
With L-(-)-tartaric acid
(-)-bicucine

(-)-bicucine

485-49-4

bicuculline

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

(+)-Bicuculline 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.

(+)-Bicuculline 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.

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