ChemicalBook > CAS DataBase List > (+)-Bicuculline

(+)-Bicuculline

Product Name
(+)-Bicuculline
CAS No.
485-49-4
Chemical Name
(+)-Bicuculline
Synonyms
NSC 3219;bicucullin;NSC 32192);Bucuculline;BICUCULLINE;D-BICUCULLINE;(+)-BICUCULINE;(+)-BICUCULLINE;PLUS-BICUCULLINE;(+)-Bicuculline-RM
CBNumber
CB3418662
Molecular Formula
C20H17NO6
Formula Weight
367.35
MOL File
485-49-4.mol
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(+)-Bicuculline Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H400Very toxic to aquatic life

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
14340
Product name
(+)-Bicuculline
Purity
≥97.0% (TLC)
Packaging
25mg
Price
$65.8
Updated
2024/03/01
Sigma-Aldrich
Product number
14340
Product name
(+)-Bicuculline
Purity
≥97.0% (TLC)
Packaging
100mg
Price
$101
Updated
2024/03/01
TCI Chemical
Product number
B1890
Product name
(+)-Bicuculline
Purity
>98.0%(HPLC)(T)
Packaging
25mg
Price
$53
Updated
2024/03/01
TCI Chemical
Product number
B1890
Product name
(+)-Bicuculline
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$154
Updated
2024/03/01
Cayman Chemical
Product number
11727
Product name
Bicuculline
Purity
≥98%
Packaging
50mg
Price
$44
Updated
2024/03/01
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(+)-Bicuculline Chemical Properties,Usage,Production

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].

(+)-Bicuculline Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (+)-Bicuculline manufacturers

Shanghai Standard Technology Co., Ltd.
Product
(+)-Bicuculline 485-49-4
Price
US $0.00/mg
Min. Order
5mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2019-11-28
Dideu Industries Group Limited
Product
(+)-Bicuculline 485-49-4
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-06-16
Career Henan Chemical Co
Product
(+)-Bicuculline 485-49-4
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-24

485-49-4, (+)-BicucullineRelated Search:

Kresoxim-methyl METHYL THIOPHENE-2-CARBOXYLATE Bensulfuron methyl Methylparaben Thiophanate-methyl Methyl acrylate Methyl acetate POLY(D-LACTIDE) Methyl Parathion-methyl Methyl bromide (-)-BICUCULLINE 1(S),9(R) METHBROMIDE,(-)-BICUCULLINE METHOBROMIDE,(-)-BICUCULLINE 1(S),9(R) METHBROMIDE,(-)-BICUCULLINE METHOBROMIDE BICUCULLINE METHYLCHLORIDE (-), [METHYL-3H],BICUCULLINE METHYLCHLORIDE (-), [METHYL-3H] (-)-BICUCULLINE METHIODIDE BICUCULLINE METHYLCHLORIDE (-), [METHYL-14C],BICUCULLINE METHYLCHLORIDE (-), [METHYL-14C] 1(s),9(r)-(-)-bicuculline methochloride,1(S),9(R)-(-)-Bicuculline methchloride,1(s),9(r)-(-)-bicuculline methochloride,1(S),9(R)-(-)-Bicuculline methchloride (-)-BICUCULLINE METHOCHLORIDE,(-)-BICUCULLINE METHOCHLORIDE (-)-BICUCULLINE METHBROMIDE

  • 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
  • (+)-Bicuculline, 99%, a GABAA antagonist
  • furo(3,4-e)-1,3-benzodioxol-8(6h)-one,6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxo
  • (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
  • 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
  • (+)-Bicuculline,98%
  • PLUS-BICUCULLINE
  • (+)-BICUCULLINE 1(S),9(R)
  • (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
  • (+)-BICUCULINE
  • (+)-BICUCULLINE
  • BICUCULLINE
  • D-BICUCULLINE
  • BICUCULLINE, (+)-(P)
  • (+)-Bicuculline &gt
  • (R)-6-((S)-6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one
  • (+)-Bicuculline USP/EP/BP
  • (+) bicuculline DISCONTINUED, offer B382500
  • Bicuculline (6CI, 7CI, 8CI)
  • (+)-Bicuculline-RM
  • (+)-Bicuculline, GABAA antagonist
  • 485-49-4
  • C20H17NO6
  • Inhibitors
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Alkaloids
  • Intermediates & Fine Chemicals
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  • GABA/Glycine receptor
  • GABA