(+)-Bicuculline Chemical Properties

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. 

2-8°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

λmax

325nm(lit.)

Merck 

14,1203

BRN 

98786

InChIKey

IYGYMKDQCDOMRE-ZWKOTPCHSA-N

CAS DataBase Reference

485-49-4(CAS DataBase Reference)

EPA Substance Registry System

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)- (485-49-4)

Safety Information

Hazard Codes 

T,N,Xn

Risk Statements 

23/24/25-50-36/37/38-20/21/22

Safety Statements 

36/37-45-61-36-26

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

MSDS

• Language:English Provider:(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
• Language:English Provider:SigmaAldrich

(+)-Bicuculline Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

GABAA receptor antagonist.

Uses

GABAa antagonist

Uses

Alkaloid naturally occurring in the d-form. Shows GABA antagonist activity.

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

+4°C

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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