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(+)-Bicuculline

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(+)-Bicuculline Basic information

Product Name:
(+)-Bicuculline
Synonyms:
  • 5-g)isoquinolin-5-yl)-,(r-(r*,s*))-lo(
  • bicucullin
  • Bucuculline
  • d-Bicuculline/(+)-Bicuculline
  • D-alkali than buttoned Spirit
  • 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)-
  • 6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-(6R)-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
CAS:
485-49-4
MF:
C20H17NO6
MW:
367.35
EINECS:
207-619-7
Product Categories:
  • Inhibitors
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Alkaloids
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • GABA/Glycine receptor
  • GABA
Mol File:
485-49-4.mol
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(+)-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. 
0-6°C
pka
4.84(at 25℃)
form 
Off-white to yellow powder.
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)
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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
10-23
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29399990
Toxicity
LD50 ipr-mus: 8480 mg/kg CUTOEX 1,199,93
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(+)-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.

Biological Activity

Classical GABA A antagonist.

Safety Profile

A poison by intraperitoneal route.When heated to decomposition it emits toxic vapors ofNOx.

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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