| Identification | More | [Name]
(+)-Bicuculline | [CAS]
485-49-4 | [Synonyms]
(+)-BICUCULINE
(+)-BICUCULLINE
BICUCULLINE
D-BICUCULLINE
(r-(r*,s*))-6-(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
[R-(R*,S*)]-6-(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
5-g)isoquinolin-5-yl)-,(r-(r*,s*))-lo(
bicucullin
furo(3,4-e)-1,3-benzodioxol-8(6h)-one,6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxo
PLUS-BICUCULLINE
(+)-BICUCULLINE 1(S),9(R)
(6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]lisoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one
NSC 3219
(+)-Bicuculline
(R-(R*,S*))-6-(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
NSC 32192)
(6R)-6-[(5S)-6-Methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[4,3-g][1,3]benzodioxol-8-one
1,3-Dioxolo[4,5-g]isoquinoline, furo[3,4-e]-1,3-benzodioxol-8(6H)-one deriv.
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*))-
(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 | [EINECS(EC#)]
207-619-7 | [Molecular Formula]
C20H17NO6 | [MDL Number]
MFCD00005006 | [Molecular Weight]
367.35 | [MOL File]
485-49-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Solid | [Melting point ]
193-197 °C | [alpha ]
D25 +130.5° (CHCl3) | [Boiling point ]
497.92°C (rough estimate) | [density ]
1.3694 (rough estimate) | [refractive index ]
1.5600 (estimate) | [storage temp. ]
0-6°C | [solubility ]
Benzene, Chloroform, DMSO, Ethyl Acetate | [form ]
Off-white to yellow powder. | [pka]
4.84(at 25℃) | [color ]
Pale Yellow | [optical activity]
[α]20/D +126±6°, c = 1% in chloroform | [Usage]
Alkaloid naturally occurring in the d-form. Shows GABA antagonist activity. | [λmax]
325nm(lit.) | [Merck ]
13,1207 | [BRN ]
98786 | [InChIKey]
IYGYMKDQCDOMRE-ZWKOTPCHSA-N | [CAS DataBase Reference]
485-49-4(CAS DataBase Reference) | [Storage Precautions]
Air sensitive;Light sensitive | [EPA Substance Registry System]
485-49-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,Xn | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R50:Very Toxic to aquatic organisms.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 1544 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
LV0909840
| [F ]
10-23 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29399990 | [Toxicity]
LD50 ipr-mus: 8480 mg/kg CUTOEX 1,199,93 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale Yellow Solid | [Uses]
Alkaloid naturally occurring in the d-form. Shows GABA antagonist activity. | [Uses]
GABAa antagonist | [Uses]
GABAA receptor antagonist. | [Definition]
ChEBI: Bicuculline is a benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species. It has a role as an agrochemical, a central nervous system stimulant, a GABA-gated chloride channel antagonist, a neurotoxin and a GABAA receptor antagonist. It is an isoquinoline alkaloid, a member of isoquinolines and a benzylisoquinoline alkaloid. | [General Description]
Bicuculline is a convulsant alkaloid. It was originally isolated from the plant Dicentra cucullaria. | [Biological Activity]
Classical GABA A antagonist. | [Biochem/physiol Actions]
(+)-Bicuculline acts as a competitive inhibitor of GABA liganding binding to the receptor. | [Safety Profile]
A poison by intraperitoneal route.When heated to decomposition it emits toxic vapors ofNOx. | [storage]
Store at -20°C, protect from light | [Purification Methods]
It crystallises from CHCl3/MeOH as plates. The crystals melt at 177o, then solidify and re-melt at 193-195o [Manske Canad J Research 21B 13 1943]. It is soluble in CHCl3, *C6H6, EtOAc but sparingly soluble in EtOH, MeOH and Et2O. [Stereochem: Blaha et al. Collect Czech Chem Commun 29 2328 1964, Snatzke et al. Tetrahedron 25 5059 1969, Pharmcol: Curtis et al. Nature 266 1222 1970, Beilstein 27 III/IV 1900]. |
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