Product Name

  • Name

    (+)-Bicuculline

  • EINECS 207-619-7
  • CAS No. 485-49-4
  • Article Data5
  • CAS DataBase
  • Density 1.473 g/cm3
  • Solubility
  • 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;
  • PSA 66.46000
  • LogP 2.52260

Synthetic route

formaldehyd
50-00-0

formaldehyd

(+)-Norbicuculline
185022-39-3

(+)-Norbicuculline

bicuculline
485-49-4

bicuculline

Conditions
ConditionsYield
With formic acid at 100℃; for 0.25h;81%
(+/-)-bicuculline
56083-00-2

(+/-)-bicuculline

bicuculline
485-49-4

bicuculline

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

(-)-bicucine

bicuculline
485-49-4

bicuculline

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

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

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

5-formyl-benzo[1,3]dioxole-4-carboxylic acid

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

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

bicuculline
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
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
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

bicuculline
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

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

bicuculline
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
methyl iodide
74-88-4

methyl iodide

bicuculline
485-49-4

bicuculline

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

bicuculline methiodide

Conditions
ConditionsYield
In chloroform for 45h; Ambient temperature;100%
phenylcarbonochloridothioate
1005-56-7

phenylcarbonochloridothioate

bicuculline
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

(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%
formaldehyd
50-00-0

formaldehyd

bicuculline
485-49-4

bicuculline

6-(9'-chloromethyl-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one
130480-93-2

6-(9'-chloromethyl-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one

Conditions
ConditionsYield
With hydrogenchloride at 48 - 50℃; for 3h;80%
bicuculline
485-49-4

bicuculline

6-(6',7'-dihydroxy-2'-methyl-1',2',3',4'-tetrahydroisoquinolin-1'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one hydrobromide
130480-92-1

6-(6',7'-dihydroxy-2'-methyl-1',2',3',4'-tetrahydroisoquinolin-1'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one hydrobromide

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -70℃;72%
bicuculline
485-49-4

bicuculline

A

C20H18N2O6

C20H18N2O6

B

C20H18N2O6

C20H18N2O6

Conditions
ConditionsYield
With chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); O-(2,4-dinitrophenyl)hydroxylamine In methanol; dichloromethane for 2h;A 65%
B 29%
bicuculline
485-49-4

bicuculline

C20H17NO7

C20H17NO7

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.5h;45%
methyl iodide
74-88-4

methyl iodide

bicuculline
485-49-4

bicuculline

adlumidiceine
51059-65-5

adlumidiceine

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
formaldehyd
50-00-0

formaldehyd

acetic acid
64-19-7

acetic acid

bicuculline
485-49-4

bicuculline

6-(9'-acetoxymethyl-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one
130480-94-3

6-(9'-acetoxymethyl-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one

Conditions
ConditionsYield
With sulfuric acid for 2h; Ambient temperature;
...Expand
phenylcarbonochloridothioate
1005-56-7

phenylcarbonochloridothioate

bicuculline
485-49-4

bicuculline

A

(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

(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

B

(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

(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; Addition; ring cleavage; Title compound not separated from byproducts;
...Expand
methyl iodide
74-88-4

methyl iodide

bicuculline
485-49-4

bicuculline

AgCl

AgCl

KOH

KOH

adlumidiceine
51059-65-5

adlumidiceine

Conditions
ConditionsYield
anschliessend Erhitzen des Methohydroxids in H2O;
...Expand
bicuculline
485-49-4

bicuculline

aobamidine
59614-38-9

aobamidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / CHCl3 / 45 h / Ambient temperature
2: 28 percent / sodium carbonate / H2O
View Scheme
bicuculline
485-49-4

bicuculline

6-(9'-aminomethyl-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one
130480-96-5

6-(9'-aminomethyl-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / concd HCl / 3 h / 48 - 50 °C
2: NH3gas / methanol / 0 - 4 °C
View Scheme
bicuculline
485-49-4

bicuculline

6-(9'-hydroxymethyl-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one
79076-81-6

6-(9'-hydroxymethyl-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concd H2SO4 / 2 h / Ambient temperature
2: 80 percent / NH3gas / methanol / 0 - 4 °C
View Scheme
bicuculline
485-49-4

bicuculline

6-(6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>-9'-(piperazin-1-ylmethyl)-isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one
130480-95-4

6-(6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>-9'-(piperazin-1-ylmethyl)-isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / concd HCl / 3 h / 48 - 50 °C
2: 86 percent / methanol / 48 h / Ambient temperature
View Scheme
bicuculline
485-49-4

bicuculline

[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-carbamic acid tert-butyl ester
130481-01-5

[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / concd HCl / 3 h / 48 - 50 °C
2: NH3gas / methanol / 0 - 4 °C
3: 90 percent / Et3N / tetrahydrofuran; H2O / 18 h
View Scheme
bicuculline
485-49-4

bicuculline

N-[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-succinamic acid
130480-97-6

N-[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-succinamic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / concd HCl / 3 h / 48 - 50 °C
2: NH3gas / methanol / 0 - 4 °C
3: 38 percent / ethanol / 1.5 h / 78 °C
View Scheme
bicuculline
485-49-4

bicuculline

4-[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester
130503-31-0

4-[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / concd HCl / 3 h / 48 - 50 °C
2: 86 percent / methanol / 48 h / Ambient temperature
3: 10 percent / Et3N / tetrahydrofuran; H2O / 48 h
View Scheme
bicuculline
485-49-4

bicuculline

(4-{[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-carbamoyl}-phenyl)-carbamic acid tert-butyl ester
130480-98-7

(4-{[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-carbamoyl}-phenyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / concd HCl / 3 h / 48 - 50 °C
2: NH3gas / methanol / 0 - 4 °C
3: 27 percent / Et3N / tetrahydrofuran / 18 h / Ambient temperature
View Scheme
bicuculline
485-49-4

bicuculline

6-(6',7'-diacetoxy-2'-methyl-1',2',3',4'-tetrahydroisoquinolin-1'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one hydrobromide
130481-00-4

6-(6',7'-diacetoxy-2'-methyl-1',2',3',4'-tetrahydroisoquinolin-1'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one hydrobromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / boron tribromide / CH2Cl2 / -70 °C
2: 77 percent / pyridine / 2 h / Ambient temperature
View Scheme
bicuculline
485-49-4

bicuculline

6-(9'-(p-aminobenzamidomethyl)-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one hydrochloride

6-(9'-(p-aminobenzamidomethyl)-6'-methyl-5',6',7',8'-tetrahydro-1',3'-dioxolo<4,5-g>isoquinolin-5'-yl)furo<3,4-e>-1,3-benzodioxol-8(6H)-one hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / concd HCl / 3 h / 48 - 50 °C
2: NH3gas / methanol / 0 - 4 °C
3: 27 percent / Et3N / tetrahydrofuran / 18 h / Ambient temperature
4: 52 percent / concd HCl, acetic acid / 1 h / Ambient temperature
View Scheme
bicuculline
485-49-4

bicuculline

N-[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-succinamic acid methyl ester; hydrochloride

N-[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-succinamic acid methyl ester; hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / concd HCl / 3 h / 48 - 50 °C
2: NH3gas / methanol / 0 - 4 °C
3: 38 percent / ethanol / 1.5 h / 78 °C
4: 100 percent / HCl / 24 h / 0 - 4 °C
View Scheme

(+)-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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