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Bicuculline

Bicuculline structure

CAS No:
485-49-4
Formula:
C20H17NO6
Chemical Name:
Bicuculline
Synonyms:
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)-;Bicuculline;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*)]-;1,3-Dioxolo[4,5-g]isoquinoline,furo[3,4-e]-1,3-benzodioxol-8(6H)-one deriv.;(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;Bicucullin;d-Bicuculline;(+)-Bicuculline;Bucuculline;NSC 32192
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

(+)-Bicuculline is a light-sensitive competitive antagonist of GABA-A receptor.

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.|Bicuculline is 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.|An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.

Bicuculline Basic Attributes

Molecular Weight：

367.35

Exact Mass：

367.35

EC Number：

207-619-7

UNII：

Y37615DVKC

NSC Number：

32192

DSSTox ID：

DTXSID3042687

HScode：

29399990

Characteristics

PSA：

66.5

XLogP3：

2.6

Appearance：

Light yellow powder.

Density：

1.5±0.1 g/cm3

Melting Point：

194 °C

Boiling Point：

542.3°C at 760 mmHg

Flash Point：

281.8±30.1 °C

Refractive Index：

1.665

Storage Conditions：

0-6°C

Vapor Pressure：

7.98E-12mmHg at 25°C

Toxicity：

Peritoneal-mouse LD50: 8.48 mg/kg

Flammability characteristics：

Combustible; burning produces toxic nitrogen oxides

Specific rotation：

D25 +130.5° (CHCl3)

Collision Cross Section：

180 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 1544 6.1/PG 2

wgk germany：

hazard class code：

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

safety instructions：

36/37-45-61-36-26

RTECS Number：

LV0909840

Marks：

T,N,Xn

Storage features：

Ventilated, low temperature and dry; stored separately from food materials in warehouse

Precautionary statement(s)：

P261-P264-P273-P280-P301 + P310-P311

Hazard Statements：

H300-H311 + H331-H400

Toxicity

Toxicity class：

most toxic

Drug Information

MeSH：

Substances that act in the brain stem or spinal cord to produce tonic or clonic convulsions, often by removing normal inhibitory tone. They were formerly used to stimulate respiration or as antidotes to barbiturate overdose. They are now most commonly used as experimental tools. (See all compounds classified as Convulsants.)|Drugs that bind to but do not activate GABA-A RECEPTORS thereby blocking the actions of endogenous or exogenous GABA-A RECEPTOR AGONISTS. (See all compounds classified as GABA-A Receptor Antagonists.)

MeSH Entry Terms：

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

Bicuculline Use and Manufacturing

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

Computed Properties

Molecular Weight:367.4
XLogP3:2.6
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:1
Exact Mass:367.10558726
Monoisotopic Mass:367.10558726
Topological Polar Surface Area:66.5
Heavy Atom Count:27
Complexity:615
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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(+)-Bicuculline

CAS No.: 485-49-4

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