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(+)-Bicuculline

CAS No.485-49-4
Chemical Name:(+)-Bicuculline
CBNumber:CB3418662
Molecular Formula:C20H17NO6
Formula Weight:367.35
MOL File:485-49-4.mol

(+)-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)
FDA UNII Y37615DVKC
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)
UNSPSC Code 12352200
NACRES NA.77

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

NFPA 704:

	0
4		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H300+H310+H330-H400
Precautionary statements P260-P262-P273-P280-P302+P352+P310-P304+P340+P310

(+)-Bicuculline Price More Price(8)

Brand: Sigma-Aldrich
Product number: 14340
Product name : (+)-Bicuculline
Purity: ≥97.0% (TLC)
Packaging: 25MG
Price: ₹6884.7
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 14340
Product name : (+)-Bicuculline
Purity: ≥97.0% (TLC)
Packaging: 25MG
Price: ₹6884.7
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich
Product number: 14340
Product name : (+)-Bicuculline
Purity: ≥97.0% (TLC)
Packaging: 100MG
Price: ₹11723.48
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 14340
Product name : (+)-Bicuculline
Purity: ≥97.0% (TLC)
Packaging: 100MG
Price: ₹11723.48
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich
Product number: 14340
Product name : (+)-Bicuculline
Purity: ≥97.0% (TLC)
Packaging: 500MG
Price: ₹30169.28
Updated: 2022/06/14
Buy: Buy

(+)-Bicuculline Chemical Properties,Usage,Production

Chemical Properties Pale Yellow Solid
Uses GABAa antagonist
Uses GABAA receptor 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].