Bicuculline (CAS 485-49-4): price, suppliers and safety

What is Bicuculline?

Plain description, key identifiers and synonyms

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 a GABAA receptor antagonist, an agrochemical, a central nervous system stimulant, a GABA-gated chloride channel antagonist and a neurotoxin. It is a benzylisoquinoline alkaloid, an isoquinoline alkaloid and a member of isoquinolines.

Identifiers

Registry numbers, names and line notations, tap to copy

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
CAS number: 485-49-4 CAS number cross-checked
EC number: 207-619-7
Molecular formula: C₂₀H₁₇NO₆
UNII: Y37615DVKC
MDL number: MFCD00005006
InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHSA-N
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
Canonical SMILES: CN1CCc2cc3c(cc2C1C1OC(=O)c2c1ccc1c2OCO1)OCO3
Isomeric SMILES: CN1CCC2=CC3=C(C=C2[C@H]1[C@H]4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3

Synonyms

d-Bicuculline
Bicculine
Bicucullin
(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
(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
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*))-
(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
(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
(6R)-6-((5S)-6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-6H-furo(4,3-g)(1,3)benzodioxol-8-one
(6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[4,3-g][1,3]benzodioxol-8-one
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
(10R)-10-((5S)-6-methyl-2H,5H,6H,7H,8H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-3,5,11-trioxatricyclo(7.3.0.02,6)dodeca-1(9),2(6),7-trien-12-one
(+)-Bicuculline
Bicuculline (+)
(R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one
(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
(6R)-6-((5S)-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxolano[4,5-g]isoquinolin-5- yl))-6-hydro-2H-1,3-dioxoleno[4,5-e]isobenzofuran-8-one
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)-
D-Bic uculline
bicuculline-(+)
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)-
(+)-Bicuculline?
Bicuculline (Standard)
Biomol-NT_000252

Show all 31 synonyms

(+)-Bicuculline, 98%
(6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]lisoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one
4-27-00-06900 (Beilstein Handbook Reference)
DivK1c_000609
PDSP2_000138
(+)-Bicuculline - Bio-X trade mark

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

No measured properties are recorded for this substance yet. Ask suppliers for a technical data sheet.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight	367.36 g/molcalc.
Exact mass	367.1056 Dacalc.
LogP (octanol/water)	2.58calc.
Topological polar surface area	66.46 Å²calc.
Hydrogen bond donors	0calc.
Hydrogen bond acceptors	7calc.
Rotatable bonds	1calc.
Heavy atoms	27calc.
Rings	6calc.
Aromatic rings	2calc.
Fraction sp3 carbons	0.35calc.
Formal charge	0calc.
Stereocentres	2calc.
Lipinski rule of five	Passes (0 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

O=C1OC(C2NCCc3cc4c(cc32)OCO4)c2ccc3c(c21)OCO3

6 rings, 26 atoms.

10 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word

Danger

Acute toxicity (severe)

Hazardous to the environment

Hazard statements

H300Fatal if swallowed.
H311Toxic in contact with skin.
H331Toxic if inhaled.
H400Very toxic to aquatic life.

Precautionary statements (18)

P261Avoid breathing dust, fume, gas, mist, vapours or spray.
P262Do not get in eyes, on skin, or on clothing.
P264Wash skin thoroughly after handling.
P270Do not eat, drink or smoke when using this product.
P271Use only outdoors or in a well-ventilated area.
P273Avoid release to the environment.
P280Wear protective gloves, protective clothing, eye protection and face protection.
P301 + P316If swallowed: Get emergency medical help immediately.
P302 + P352If on skin: Wash with plenty of water.
P304 + P340If inhaled: Remove person to fresh air and keep comfortable for breathing.
P316Get emergency medical help immediately.
P321Specific treatment (see supplemental first aid instructions on the label).
P330Rinse mouth.
P361 + P364Take off immediately all contaminated clothing. And wash it before reuse.
P391Collect spillage.
P403 + P233Store in a well-ventilated place. Keep container tightly closed.
P405Store locked up.
P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Bicuculline suppliers

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All 79 suppliers

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AvaChem Scientific LLC
United StatesUnclaimed profile
BicucullineGrade, purity and minimum order on request
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Enzo Life Sciences International Inc.
United States ManufacturerUnclaimed profile
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Conscientia Industrial Co Ltd
China, Taizhou ManufacturerUnclaimed profile
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Molekula GmbH
United Kingdom, München ManufacturerUnclaimed profile
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Shandong Engineering Technology Research Center for Reference materials of (CTM)
ChinaUnclaimed profile
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Nacalai Tesque, Inc.
JapanUnclaimed profile
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Chemleader Biomedical Co., Ltd.
China, Shanghai ManufacturerUnclaimed profile
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Kunming Zehao Science & Technology Co., Ltd.
China, KunmingUnclaimed profile
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P&S Chemicals
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001Chemical
China, HangzhouUnclaimed profile
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Suppliers marked Unclaimed profile have not claimed their profile yet. They are not verified by CompoundList, their offers are price on request and details may have changed, so please confirm them with the supplier. Company representatives can claim a profile with a business email on the company's own website domain. Our team verifies each claim and sends the result by email.

Where suppliers are based

79 suppliers in 14 countries

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Bicuculline price

Indicative price range per kg from live supplier offers

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Suppliers quote this chemical on request. Send one free request and compare quotes side by side.

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Uses and applications

What the substance is used for, by industry and function

Pharmacological actions

Convulsants
GABA-A Receptor Antagonists

Roles

GABA agent
GABA antagonist
GABA-gated chloride channel antagonist
GABAA receptor antagonist
aetiopathogenetic role
agrochemical
antagonist
biophysical role
central nervous system drug
central nervous system stimulant
membrane transport modulator
neurotoxin
neurotransmitter agent
pharmaceutical
poison

Regulatory status

Inventories, regulations and trade controls that list this substance

No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Bicuculline is traded under.

HS 2934.99Indicative HS code

Nucleic acids and their salts, other heterocyclic compounds, not elsewhere classified in heading 2934

World exports in 2024

$26.7B

+15.0% vs 2023, imports $26.3B

2019 to 2024

Top exporters

Ireland26.3%
China15.7%
Singapore10.3%

Top importers

Reported customs values in USD, not prices.Full trade data

The HS code shown for Bicuculline is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Parent and salt forms, stereoisomers, similar structures and isomers

Stereoisomers and isotopic forms

Same connectivity, different stereochemistry or isotopes (same InChIKey skeleton)

(6S)-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 chemical structure, C20H17NO6, CAS 550-49-2

(6S)-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)-one550-49-2C₂₀H₁₇NO₆

Capnoidine chemical structure, C20H17NO6, CAS 485-50-7

Capnoidine485-50-7C₂₀H₁₇NO₆

(-)-Bicuculline chemical structure, C20H17NO6, CAS 56083-00-2

(-)-Bicuculline56083-00-2C₂₀H₁₇NO₆

Similar structures

Nearest neighbours by Morgan fingerprint Tanimoto similarity

1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]- chemical structure, C21H21NO6, CAS 60594-55-0

(-)-Hydrastine chemical structure, C21H21NO6, CAS 118-08-1

Egenine chemical structure, C20H19NO6, CAS 6883-44-9

63% similar

Egenine6883-44-9C₂₀H₁₉NO₆1 supplier

1,3-Dioxolo(4,5-g)isoquinolinium, 5-((6R)-6,8-dihydro-8-oxofuro(3,4-e)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, iodide (1:1), (5S)- chemical structure, C21H20INO6, CAS 40709-69-1

(R-(R*,S*))-5-(6,8-Dihydro-8-oxofuro(3,4-e)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-1,3-dioxolo(4,5-g)isoquinolinium bromide chemical structure, C21H20BrNO6, CAS 73604-30-5

(-)-Bicuculline methiodide chemical structure, C21H20INO6, CAS 55950-07-7

Bicuculline methobromide chemical structure, C21H20BrNO6, CAS 66016-70-4

Bicuculline methochloride chemical structure, C21H20ClNO6, CAS 38641-83-7

Same formula isomers

Different compounds that share this molecular formula

All isomers

(2S)-5-(Benzyloxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid chemical structure, C20H17NO6, CAS 88784-33-2

(2S)-5-(Benzyloxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid88784-33-2C₂₀H₁₇NO₆1 supplier

Nitrofarin chemical structure, C20H17NO6, CAS 17298-36-1

Nitrofarin17298-36-1C₂₀H₁₇NO₆

4-Acetyl-2-methoxyphenyl 2-(1,3-dioxoisoindolin-2-yl)propanoate chemical structure, C20H17NO6, CAS 304672-97-7

4-Acetyl-2-methoxyphenyl 2-(1,3-dioxoisoindolin-2-yl)propanoate304672-97-7C₂₀H₁₇NO₆

4-[2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-oxoethyl]-2-methyl-1,4-benzoxazepine-3,5(2H,4H)-dione chemical structure, C20H17NO6, CAS 903862-81-7

4-[2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-oxoethyl]-2-methyl-1,4-benzoxazepine-3,5(2H,4H)-dione903862-81-7C₂₀H₁₇NO₆

9-(2,5-Dimethoxyphenyl)-6,9-dihydro[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-one chemical structure, C20H17NO6, CAS 866050-83-1

9-(2,5-Dimethoxyphenyl)-6,9-dihydro[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-one866050-83-1C₂₀H₁₇NO₆

1-(4-Methoxyphenyl)-1-oxopropan-2-yl 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetate chemical structure, C20H17NO6, CAS 853903-30-7

1-(4-Methoxyphenyl)-1-oxopropan-2-yl 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetate853903-30-7C₂₀H₁₇NO₆

2-(3-Methoxyphenyl)-2-oxoethyl 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate chemical structure, C20H17NO6, CAS 432538-39-1

2-(3-Methoxyphenyl)-2-oxoethyl 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate432538-39-1C₂₀H₁₇NO₆

(2-Benzamido-2-oxoethyl) 5-methoxy-3-methyl-1-benzofuran-2-carboxylate chemical structure, C20H17NO6, CAS 1001889-06-0

(2-Benzamido-2-oxoethyl) 5-methoxy-3-methyl-1-benzofuran-2-carboxylate1001889-06-0C₂₀H₁₇NO₆

2-(2-Methoxyphenyl)-2-oxoethyl 3-(1,3-dioxoisoindolin-2-yl)propanoate chemical structure, C20H17NO6, CAS 923680-50-6

2-(2-Methoxyphenyl)-2-oxoethyl 3-(1,3-dioxoisoindolin-2-yl)propanoate923680-50-6C₂₀H₁₇NO₆

Hypecorinine chemical structure, C20H17NO6, CAS 41787-57-9

Hypecorinine41787-57-9C₂₀H₁₇NO₆

Pareirubrine A chemical structure, C20H17NO6, CAS 147044-68-6

Pareirubrine A147044-68-6C₂₀H₁₇NO₆

3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-oxo-4H-chromen-7-yl dimethylcarbamate chemical structure, C20H17NO6, CAS 724740-81-2

3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-oxo-4H-chromen-7-yl dimethylcarbamate724740-81-2C₂₀H₁₇NO₆

Frequently asked questions

Quick answers about Bicuculline, based on the data on this page

What is Bicuculline?

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.

What is the CAS number of Bicuculline?

The CAS registry number of Bicuculline is 485-49-4.

What is the molecular formula and weight of Bicuculline?

The molecular formula of Bicuculline is C20H17NO6 and its molar mass is 367.36 g/mol.

What is Bicuculline used for?

Known uses and roles of Bicuculline include gaba agent, gaba antagonist, gaba-gated chloride channel antagonist, gabaa receptor antagonist, aetiopathogenetic role and 12 more.

Is Bicuculline hazardous?

Bicuculline carries the GHS signal word "Danger". Main hazards: fatal if swallowed, toxic in contact with skin, toxic if inhaled. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Bicuculline?

Bicuculline is usually classified under HS code 293499 (Nucleic acids and their salts, whether or not chemically defined, other heterocyclic…). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Bicuculline?

CompoundList lists 79 suppliers of Bicuculline in United States, China, United Kingdom, Germany and 10 more. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

What is the price of Bicuculline?

Suppliers quote Bicuculline on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Bicuculline

Bicuculline

Key facts

What is Bicuculline?

Identifiers

Synonyms

Physical and chemical properties

Physical and chemical properties

Computed descriptors

Murcko scaffold

Safety and hazards

Hazard statements

Bicuculline suppliers

Where suppliers are based

Send one request to many suppliers

Bicuculline price

Uses and applications

Pharmacological actions

Roles

Regulatory status

HS code and trade data

Global trade

Frequently asked questions

What is Bicuculline?

What is the CAS number of Bicuculline?

What is the molecular formula and weight of Bicuculline?

What is Bicuculline used for?

Is Bicuculline hazardous?

What is the HS code of Bicuculline?

Where can I buy Bicuculline?

What is the price of Bicuculline?

Guides for buyers

Get quotes for Bicuculline

Key facts

What is Bicuculline?

Identifiers

Synonyms

Physical and chemical properties

Physical and chemical properties

Computed descriptors

Murcko scaffold

Safety and hazards

Hazard statements

Bicuculline suppliers

Where suppliers are based

Send one request to many suppliers

Bicuculline price

Uses and applications

Pharmacological actions

Roles

Regulatory status

HS code and trade data

Global trade

Related chemicals

Stereoisomers and isotopic forms

Similar structures

Same formula isomers

Frequently asked questions

What is Bicuculline?

What is the CAS number of Bicuculline?

What is the molecular formula and weight of Bicuculline?

What is Bicuculline used for?

Is Bicuculline hazardous?

What is the HS code of Bicuculline?

Where can I buy Bicuculline?

What is the price of Bicuculline?

Guides for buyers

Get quotes for Bicuculline