(+)-Bicuculline

Modify Date: 2025-08-22 23:03:31

(+)-Bicuculline structure	Common Name	(+)-Bicuculline
	CAS Number	485-49-4	Molecular Weight	367.352
	Density	1.5±0.1 g/cm3	Boiling Point	542.3±50.0 °C at 760 mmHg
	Molecular Formula	C₂₀H₁₇NO₆	Melting Point	196-198 ºC
	MSDS	Chinese USA	Flash Point	281.8±30.1 °C
	Symbol	GHS06, GHS09	Signal Word	Danger

Use of (+)-Bicuculline

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

Name	bicuculline
Synonym	More Synonyms

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.

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.

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
InChIKey	IYGYMKDQCDOMRE-ZWKOTPCHSA-N
SMILES	CN1CCc2cc3c(cc2C1C1OC(=O)c2c1ccc1c2OCO1)OCO3

(+)-Bicuculline MSDS(Chinese)

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

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)

Formaldehyde

CAS#:50-00-0

N/A

CAS#:185022-39-3

~81%

(+)-Bicuculline

CAS#:485-49-4

Literature: Kardos; Blandl; Luyen; Doernyei; Gacs-Baitz; Simonyi; Cash; Blasko; Szantay European Journal of Medicinal Chemistry, 1996 , vol. 31, # 10 p. 761 - 765

(+)-bicuculline

CAS#:56083-00-2

(+)-Bicuculline

CAS#:485-49-4

Literature: Haworth; Pinder; Robinson Nature (London, United Kingdom), 1950 , vol. 165, p. 529

Furo[3,4-e]-1,3...

CAS#:64395-07-9

(+)-Bicuculline

CAS#:485-49-4

Literature: Kardos; Blandl; Luyen; Doernyei; Gacs-Baitz; Simonyi; Cash; Blasko; Szantay European Journal of Medicinal Chemistry, 1996 , vol. 31, # 10 p. 761 - 765

5-formyl-1,3-be...

CAS#:58343-48-9

(+)-Bicuculline

CAS#:485-49-4

Literature: Kardos; Blandl; Luyen; Doernyei; Gacs-Baitz; Simonyi; Cash; Blasko; Szantay European Journal of Medicinal Chemistry, 1996 , vol. 31, # 10 p. 761 - 765

N/A

CAS#:1026278-40-9

(+)-Bicuculline

CAS#:485-49-4

Literature: Kardos; Blandl; Luyen; Doernyei; Gacs-Baitz; Simonyi; Cash; Blasko; Szantay European Journal of Medicinal Chemistry, 1996 , vol. 31, # 10 p. 761 - 765

N-(2-(benzo[d][...

CAS#:185022-35-9

(+)-Bicuculline

CAS#:485-49-4

Literature: Kardos; Blandl; Luyen; Doernyei; Gacs-Baitz; Simonyi; Cash; Blasko; Szantay European Journal of Medicinal Chemistry, 1996 , vol. 31, # 10 p. 761 - 765

Precursor 5
CAS#:50-00-0 Formaldehyde CAS#:56083-00-2 (+)-bicuculline CAS#:64395-07-9 Furo[3,4-e]-1,3... CAS#:58343-48-9 5-formyl-1,3-be...
CAS#:185022-35-9 N-(2-(benzo[d][...
DownStream 1
CAS#:40709-69-1 Bicuculline met...

Radixin regulates synaptic GABAA receptor density and is essential for reversal learning and short-term memory.

Nat. Commun. 6 , 6872, (2015)

Neurotransmitter receptor density is a major variable in regulating synaptic strength. Receptors rapidly exchange between synapses and intracellular storage pools through endocytic recycling. In addit...

Reduced SNAP-25 increases PSD-95 mobility and impairs spine morphogenesis.

Cell Death Differ. 22 , 1425-36, (2015)

Impairment of synaptic function can lead to neuropsychiatric disorders collectively referred to as synaptopathies. The SNARE protein SNAP-25 is implicated in several brain pathologies and, indeed, bra...

Forebrain NR2B overexpression enhancing fear acquisition and long-term potentiation in the lateral amygdala.

Eur. J. Neurosci. 42 , 2214-23, (2015)

N-methyl-d-aspartic acid (NMDA) receptor-dependent long-term potentiation (LTP) at the thalamus-lateral amygdala (T-LA) synapses is the basis for acquisition of auditory fear memory. However, the role...

Name: In vitro displacement of [3H]muscimol from Gamma-aminobutyric acid A receptor of rat ...
Source: ChEMBL
Target: Gamma-aminobutyric acid receptor subunit alpha-3
External Id: CHEMBL681563

Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN

Name: Primary qHTS assay for small molecule inhibitors of Inositol hexaphosphate kinase 1 (...
Source: NCGC
External Id: IP6K1-p1

Name: QFRET-based biochemical primary high throughput screening assay to identify exosite i...
Source: The Scripps Research Institute Molecular Screening Center
Target: disintegrin and metalloproteinase domain-containing protein 17 preproprotein [Homo sapiens]
External Id: ADAM17_INH_QFRET_1536_1X%INH PRUN

Name: Inhibition of neurosphere proliferation of mouse neural precursor cells by MTT assay
Source: ChEMBL
Target: N/A
External Id: CHEMBL1266185

Name: ERK5 transcriptional activity HTS
Source: 24565
Target: N/A
External Id: ERK5 transcriptional activity-HTS

Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN

Name: uHTS identification of small molecule activators of the adaptive arm of the Unfolded ...
Source: Burnham Center for Chemical Genomics
Target: N/A
External Id: BCCG-A405-UPR-XBP1-PrimaryAgonist-Assay

Name: Rescue cell viability in cybrid cells with a genetic mutation in complex 1 of the mit...
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
Target: N/A
External Id: HMS1315

Name: Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); ...
Source: ChEMBL
Target: Klebsiella pneumoniae
External Id: CHEMBL4296186

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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

bicucullin

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(+)-Bicuculline

Use of (+)-Bicuculline

Names

(+)-Bicuculline Biological Activity

Chemical & Physical Properties

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

Safety Information

Synthetic Route

Precursor & DownStream

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(+)-BicucullineBioassay

Synonyms

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