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Product No: AU0349

(+)-Bicuculline, >98.0%(T)(HPLC)

Name: (+)-Bicuculline
Brand: Chempure

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CAS Number

485-49-4

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IUPAC name	(6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
inchi	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
inchi key	IYGYMKDQCDOMRE-ZWKOTPCHSA-N
molecular formula	C20H17NO6
synonyms	bicuculline (+)-Bicuculline 485-49-4 d-Bicuculline Bicculine
Compound Description	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 -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. Bicuculline has been reported in Corydalis repens, Corydalis decumbens, and other organisms with data available. 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. Since it blocks the inhibitory action of GABA receptors, the action of bicuculline mimics epilepsy. This property is utilized in laboratories across the world in the in vitro study of epilepsy, generally in hippocampal or cortical neurons in prepared brain slices from rodents. This compound is also routinely used to isolate glutamatergic receptor function. An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.

Computed Properties

Molecular Weight:	367.4 g/mol
XLogP3:	2.6
Hydrogen Bond Donor Count:	0
Hydrogen Bond Acceptor Count:	7
Rotatable Bond Count:	1
Exact Mass:	367.10558726 g/mol
Monoisotopic Mass:	367.10558726 g/mol
Topological Polar Surface Area:	66.5 Å²
Heavy Atom Count:	27
Formal Charge:	0
Complexity:	615
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	2
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Danger
hazard classes and categories	Acute Tox. 1 (97.4%) Acute Tox. 3 (100%) Aquatic Acute 1 (97.4%)
precautionary statement codes	P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P391, P403+P233, P405, and P501
hazard statements	H300 (97.4%): Fatal if swallowed [Danger Acute toxicity, oral] H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal] H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation] H400 (97.4%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

toxicity summary	The action of bicuculline is primarily on the ionotropic GABAA receptors, which are ligand-gated ion channels concerned chiefly with the passing of chloride ions across the cell membrane, thus promoting an inhibitory influence on the target neuron. These receptors are the major targets for benzodiazepines and related anxiolytic drugs. The half-maximal inhibitory concentration of bicuculline on GABAA receptors is 3 μM. In addition to being a potent GABAA receptor antagonist, bicuculline can be used to block Ca2+-activated potassium channels. Sensitivity to bicuculline is defined by IUPHAR as a major criterion in the definition of GABAA receptors.
symptoms
carcinogen classification	default_key: No indication of carcinogenicity to humans .

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About this item

IUPAC name	(6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
inchi	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
inchi key	IYGYMKDQCDOMRE-ZWKOTPCHSA-N
molecular formula	C20H17NO6
synonyms	bicuculline (+)-Bicuculline 485-49-4 d-Bicuculline Bicculine
Compound Description	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 -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. Bicuculline has been reported in Corydalis repens, Corydalis decumbens, and other organisms with data available. 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. Since it blocks the inhibitory action of GABA receptors, the action of bicuculline mimics epilepsy. This property is utilized in laboratories across the world in the in vitro study of epilepsy, generally in hippocampal or cortical neurons in prepared brain slices from rodents. This compound is also routinely used to isolate glutamatergic receptor function. An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.

Computed Properties

Molecular Weight:	367.4 g/mol
XLogP3:	2.6
Hydrogen Bond Donor Count:	0
Hydrogen Bond Acceptor Count:	7
Rotatable Bond Count:	1
Exact Mass:	367.10558726 g/mol
Monoisotopic Mass:	367.10558726 g/mol
Topological Polar Surface Area:	66.5 Å²
Heavy Atom Count:	27
Formal Charge:	0
Complexity:	615
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	2
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Danger
hazard classes and categories	Acute Tox. 1 (97.4%) Acute Tox. 3 (100%) Aquatic Acute 1 (97.4%)
precautionary statement codes	P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P391, P403+P233, P405, and P501
hazard statements	H300 (97.4%): Fatal if swallowed [Danger Acute toxicity, oral] H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal] H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation] H400 (97.4%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

toxicity summary	The action of bicuculline is primarily on the ionotropic GABAA receptors, which are ligand-gated ion channels concerned chiefly with the passing of chloride ions across the cell membrane, thus promoting an inhibitory influence on the target neuron. These receptors are the major targets for benzodiazepines and related anxiolytic drugs. The half-maximal inhibitory concentration of bicuculline on GABAA receptors is 3 μM. In addition to being a potent GABAA receptor antagonist, bicuculline can be used to block Ca2+-activated potassium channels. Sensitivity to bicuculline is defined by IUPHAR as a major criterion in the definition of GABAA receptors.
symptoms
carcinogen classification	default_key: No indication of carcinogenicity to humans .

Product No: AU0349

(+)-Bicuculline, >98.0%(T)(HPLC)

Product No: AU0349

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

TOXICITY

About this item

Documentation

Certificate of Analysis

Require a Sample Certificate of Analysis (COA) ?

Reviews

Product No: AU0349

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

TOXICITY

Require a Sample Certificate of Analysis (COA) ?