(+)-Bicuculline

Names

[ CAS No. ]:
485-49-4

[ Name ]:
(+)-Bicuculline

[Synonym ]:
D-BICUCULLINE
EINECS 207-619-7
BICUCULLINE (+)
(+)-Bicuculline
PLUS-BICUCULLINE
bicucculine
(6R)-6-[(5S)-6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one
MFCD00005006
Bicuculline
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)-
bicucullin

Biological Activity

[Description]:

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

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Natural Products >> Alkaloid

Research Areas >> Others

[References]

[1]. Zahm DS, et al. Comparison of the locomotor-activating effects of bicuculline infusions into the preoptic area and ventral pallidum. Brain Struct Funct. 2014 Mar;219(2):511-26.

[2]. Johnston GA. Advantages of an antagonist: bicuculline and other GABA antagonists. Br J Pharmacol. 2013 May;169(2):328-36.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
542.3±50.0 °C at 760 mmHg

[ Melting Point ]:
196-198 ºC

[ Molecular Formula ]:
C₂₀H₁₇NO₆

[ Molecular Weight ]:
367.352

[ Flash Point ]:
281.8±30.1 °C

[ Exact Mass ]:
367.105591

[ PSA ]:
66.46000

[ LogP ]:
2.88

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.665

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LV0909840

CHEMICAL NAME :: 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*))-

CAS REGISTRY NUMBER :: 485-49-4

BEILSTEIN REFERENCE NO. :: 0098786

LAST UPDATED :: 199801

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C20-H17-N-O6

MOLECULAR WEIGHT :: 367.38

WISWESSER LINE NOTATION :: T C566 DO FO KN EH&&TJ K1 J- ET B565 CVO JO LO EH KHJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8480 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CUTOEX Current Toxicology. (Nova Science Publishers, Inc., 6080 Jericho Turnpike, Suite 207, Commack, NY 11725) V.1 1993- Volume(issue)/page/year: 1,199,1993

Safety Information

[ Symbol ]:

GHS06, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H311 + H331-H400

[ Precautionary Statements ]:
P261-P264-P273-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;N: Dangerous for the environment;

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S36/37-S45-S61

[ RIDADR ]:
UN 1544 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
LV0909840

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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