ChemicalBook CAS DataBase List 485-49-4

485-49-4

Name	(+)-Bicuculline
CAS	485-49-4
EINECS(EC#)	207-619-7
Molecular Formula	C20H17NO6
MDL Number	MFCD00005006
Molecular Weight	367.35
MOL File	485-49-4.mol

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

Chemical Properties

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 Rotation	[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
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
InChIKey	IYGYMKDQCDOMRE-ZWKOTPCHSA-N
SMILES	[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@@]4([H])N(C)CCc5cc6OCOc6cc45
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

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 . less more
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 . less more
RIDADR	UN 1544 6.1/PG 2
WGK Germany	3
RTECS	LV0909840
F	10-23
HazardClass	6.1(b)
PackingGroup	III
HS Code	29399990
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 2 Dermal Acute Tox. 2 Inhalation Acute Tox. 2 Oral Aquatic Acute 1
Toxicity	LD50 ipr-mus: 8480 mg/kg CUTOEX 1,199,93 less more

Hazard Information

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].

Material Safety Data Sheet(MSDS)

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

J & K SCIENTIFIC LTD.

Telephone18210857532 18210857532

Websitehttps://www.jkchemical.com

3B Pharmachem (Wuhan) International Co.,Ltd.

Telephone 18930552037

Websitehttps://www.chemicalbook.com/ShowSupplierProductsList13285/0_EN.htm

Chembest Research Laboratories Limited

Telephone021-20908456

Websitehttp://www.BioChemBest.com

TCI (Shanghai) Development Co., Ltd.

Telephone021-67121386

Websitehttps://www.tcichemicals.com/CN/zh/

Nanjing Chemlin Chemical Co., Ltd

Telephone025-83697070 13770331960

Websitehttp://www.echemlin.cn

Chemsky（shanghai）International Co.,Ltd.

Telephone021-50135380

Websitehttp://www.shchemsky.com

China DongFan Chemical Co.,LTD

Telephone86-0571-85151182

Websitehttps://www.chemicalbook.com/ShowSupplierProductsList14819/0_EN.htm

Shandong Xiya Chemical Co., Ltd

Telephone13355009207 13355009207

Websitehttp://www.xiyashiji.com

Sichuan Kulinan Technology Co., Ltd

Telephone400-1166-196 18981987031

Websitehttp://www.hx-r.com/

Shenzhen Sungening Bio-Tech Co., Ltd

Telephone+86-0755-89668383

Websitehttp://www.sungening.com/en

Dalian Meilun Biotech Co., Ltd.

Telephone0411-62910999 13889544652

Websitehttp://www.meilunbio.com/

Wuhan Haizheng Industry & Trade Development Co. Ltd

Telephone027-8866 0053/88660577/88660578

Websitehttps://www.chemicalbook.com/ShowSupplierProductsList15548/0_EN.htm

BioBioPha Co., Ltd.

Telephone0871-65217109

Websitehttp://www.biobiopha.com

ShangHai YuanYe Biotechnology Co., Ltd.

Telephone 15026964105

Websitehttp://www.shyuanye.com

Chengdu Ai Keda Chemical Technology Co., Ltd.

Telephone4008-755-333 18080918076

Websitehttp://www.aikeshiji.com

Chengdu Biopurify Phytochemicals Ltd.

Telephone+86-028-82633397 18982077548

Websitehttp://www.biopurify.cn

Chengdu Climax Biotech Co., Ltd.

Telephone028-83311324 1278112614

Websitehttp://www.climax-biotech.com

Beijing HuaMeiHuLiBiological Chemical

Telephone010-56205725

Websitehttp://www.huabeibiochem.com/

1of4

Related Products

Send Inquriy