Coptisine supplier | CasNO.3486-66-6

Name
COPTISINE
EINECS
CAS No. 3486-66-6
Article Data6
CAS DataBase
Density g/cm³
Solubility
Melting Point 212-217 °C
Formula C19H14 N O4
Boiling Point °Cat760mmHg
Molecular Weight 320.324
Flash Point °C
Transport Information
Appearance
Safety A poison by ingestion. When heated to decomposition it emits toxic vapors of NO_x.
Risk Codes A poison.:;
Molecular Structure
Hazard Symbols A poison.
Synonyms Berbinium,7,8,13,13a-tetradehydro-2,3:9,10-bis(methylenedioxy)- (8CI); Alkaloid A, fromCoptis groenlandica; Coptisin; Coptisine; YHL II
PSA 40.80000
LogP 2.80780

Synthetic route

: C19H15NO5

: 3486-66-6
coptisine

Conditions

Conditions	Yield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h;	74%

: 2086-83-1
berberine

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multistep reaction;

: 75-09-2
dichloromethane

: 2,3,9,10-tetrahydroxy-protoberberine chloride

: 3486-66-6
coptisine

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 40 - 90℃; for 5h; Inert atmosphere;

: 130-86-9
protopine

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride / chloroform / 1 h / Reflux 2: dimethyl sulfoxide / 25.5 h / 115 - 120 °C View Scheme

: 20105-28-6
N-Methyl-dihydrocoptisinium-Kation

: 3486-66-6
coptisine

Conditions

Conditions	Yield
In dimethyl sulfoxide at 115 - 120℃; for 25.5h;

: 53777-78-9
Dihydrocoptisine

: 3486-66-6
coptisine

Conditions

Conditions	Yield
With iodine; potassium acetate In ethanol at 20℃; Inert atmosphere;	5.5 mg

: 94143-83-6
5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 steps
1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve
2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere
3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere
4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve
5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere
6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere
7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere
View Scheme

: C20H16BrNO4

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 3: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 4: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 5: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 5 steps
1: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere
2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve
3: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere
4: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere
5: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere
View Scheme

: 72744-54-8
5-bromo-benzo[1,3]dioxole-4-carbaldehyde

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme

Yield

: C20H17NO4

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 2: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 4: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve
2: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere
3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere
4: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere
View Scheme

: C23H24BrNO4Si

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 2: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 3: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 4: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 5: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 6: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 6 steps
1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere
2: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere
3: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve
4: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere
5: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere
6: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere
View Scheme

: 13-carboxaldehyde-8-oxocoptisine

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 2: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 3: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme

: 19716-61-1
coptisinone

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 2: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme

: C9H6ClNO2

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 90 °C / Inert atmosphere 2: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 3: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C View Scheme

: 7-chloro-[1,3]dioxolo[4,5-h]isoquinoline

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 2: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C View Scheme

: C10H8ClNO2

: 3486-66-6
coptisine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: boron tribromide / dichloromethane / 2 h / -78 - -30 °C / Inert atmosphere 2: potassium carbonate / dimethyl sulfoxide / 90 °C / Inert atmosphere 3: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 4: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C View Scheme

: 3486-66-6
coptisine

: 67-64-1
acetone

: (±)-8-acetonyldihydrocoptisine

Conditions

Conditions	Yield
With sodium hydroxide at 20℃; for 1h;	69.8%

: 3486-66-6
coptisine

: 84229-86-7
C19H13NO5

: 3486-66-6
coptisine

: 77-78-1
dimethyl sulfate

: 107651-12-7
C20H18NO4(1+)*CH3O4S(1-)

Conditions

Conditions	Yield
With lithium aluminium tetrahydride 1.) THF; 2.) benzene; Yield given. Multistep reaction;

: 3486-66-6
coptisine

: 107651-13-8
C20H15NO5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) LiAlH4 / 1.) THF; 2.) benzene 2: 1.) 25percent KOH; 2.) m-chloroperoxybenzoic acid / 1.) MeOH; 2.) CH2Cl2 View Scheme

: 3486-66-6
coptisine

: 107651-14-9, 107651-15-0
(6S,7S)-8-Methyl-7-(6-vinyl-benzo[1,3]dioxol-5-yl)-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinolin-6-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) LiAlH4 / 1.) THF; 2.) benzene 2: 1.) 25percent KOH; 2.) m-chloroperoxybenzoic acid / 1.) MeOH; 2.) CH2Cl2 3: 80 percent / sodium borohydride / methanol / Heating View Scheme

: 3486-66-6
coptisine

: 107651-14-9, 107651-15-0
(6R,7S)-8-Methyl-7-(6-vinyl-benzo[1,3]dioxol-5-yl)-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinolin-6-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) LiAlH4 / 1.) THF; 2.) benzene 2: 1.) 25percent KOH; 2.) m-chloroperoxybenzoic acid / 1.) MeOH; 2.) CH2Cl2 3: 15 percent / sodium borohydride / methanol / Heating View Scheme

: 3486-66-6
coptisine

: 84229-91-4
7,8,6',8'-tetrahydro-6H-(7'rN)-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6't,8'c-diol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: 64 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating 3: 67 percent / Heating 4: 74 percent / aq. KOH; dioxane / 48 h / Heating View Scheme

: 3486-66-6
coptisine

: 24181-64-4, 33805-02-6, 68736-95-8, 76231-96-4, 99265-30-2, 126187-21-1
(+/-)-ochrobirine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: 61 percent 3: 89 percent / AgOAc 4: LiAlH4 View Scheme
Multi-step reaction with 5 steps 2: 64 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating 3: 67 percent / Heating 4: 74 percent / aq. KOH; dioxane / 48 h / Heating 5: 73 percent / tetrahydrofuran / Ambient temperature View Scheme

: 3486-66-6
coptisine

: C20H13NO7

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: 61 percent 3: 89 percent / AgOAc View Scheme

: 3486-66-6
coptisine

: 84229-89-0
C20H15NO7

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: 64 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating 3: 67 percent / Heating View Scheme

: 3486-66-6
coptisine

: C22H18ClNO7

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 61 percent View Scheme

: 3486-66-6
coptisine

: 84229-87-8, 84277-21-4
C19H15NO5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 20 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating View Scheme

: 3486-66-6
coptisine

: 84229-87-8, 84277-21-4
C19H15NO5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 64 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating View Scheme

: 3486-66-6
coptisine

: 24181-64-4, 33805-02-6, 68736-95-8, 76231-96-4, 99265-30-2, 126187-21-1
C20H19NO6

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: 61 percent 3: 89 percent / AgOAc 4: LiAlH4 View Scheme

: 3486-66-6
coptisine

: 1427306-71-5
13-nitro-8-oxocoptisine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: nitric acid / dichloromethane / 0.5 h / 20 - 30 °C / Reflux; Inert atmosphere View Scheme

: 3486-66-6
coptisine

: 1427306-72-6
12,13-dinitro-8-oxocoptisine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: nitric acid / dichloromethane / 20 °C / Inert atmosphere View Scheme

: 3486-66-6
coptisine

: 1427306-73-7
1,2-methylenedioxy-9,10-dihydroxyl-12-sulfonyl-8-oxoprotoberberine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: sulfuryl dichloride / dichloromethane / 2 h / 0 °C / Inert atmosphere View Scheme

: 3486-66-6
coptisine

: 1427306-74-8
8-thiocoptisine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: tetraphosphorus decasulfide / pyridine; dichloromethane / 3 h / Reflux; Inert atmosphere View Scheme

: 3486-66-6
coptisine

: 1427306-75-9
13-bromo-8-thiocoptisine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / 8 h / 80 °C 2: N-Bromosuccinimide / chloroform / 24 h / 20 °C / Reflux; Inert atmosphere 3: tetraphosphorus decasulfide / pyridine; dichloromethane / 3 h / Reflux; Inert atmosphere View Scheme

: 3486-66-6
coptisine

: 1427306-76-0
13-nitro-8-thiocoptisine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / 8 h / 80 °C 2: nitric acid / dichloromethane / 0.5 h / 20 - 30 °C / Reflux; Inert atmosphere 3: tetraphosphorus decasulfide / pyridine; dichloromethane / 3 h / Reflux; Inert atmosphere View Scheme

: 3486-66-6
coptisine

: 1427306-77-1
12,13-dinitro-8-thiocoptisine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / 8 h / 80 °C 2: nitric acid / dichloromethane / 20 °C / Inert atmosphere 3: tetraphosphorus decasulfide / pyridine; dichloromethane / 3 h / Reflux; Inert atmosphere View Scheme

: 3486-66-6
coptisine

: 1427306-70-4
13-bromo-8-oxocoptisine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: N-Bromosuccinimide / chloroform / 24 h / 20 °C / Reflux; Inert atmosphere View Scheme

: 3486-66-6
coptisine

: 19716-61-1
coptisinone

Conditions

Conditions	Yield
With potassium hydroxide at 80℃; for 8h;	28 mg
With sodium hydroxide; potassium hexacyanoferrate(III) In water Reflux;

: 3486-66-6
coptisine

: 75-03-6
ethyl iodide

: 1427306-68-0
2,3,9,10-tetraethoxy-8-oxoprotoberberine

Conditions

Conditions	Yield
With potassium hydroxide at 80℃; for 8h; Inert atmosphere;	39 mg

: 3486-66-6
coptisine

: 107-08-4
1-iodo-propane

: 1427306-69-1
2,3,9,10-tetrapropoxy-8-oxoprotoberberine

Conditions

Conditions	Yield
at 80℃; for 8h; Inert atmosphere;	36 mg

: 3486-66-6
coptisine

: 107-06-2
1,2-dichloro-ethane

: 1427306-67-9
2,3-ethylenedioxy-9,10-ethylenedioxy-8-oxoprotoberbeirine

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 80℃; for 8h; Inert atmosphere;	33 mg

Coptisine Chemical Properties

Product Name: Coptisine
Synonyms of Coptisine (CAS NO.3486-66-6) : [1,3]Benzodioxolo[5,6-a]-1,3-benzodioxolo[4,5-g]quinolizinium, 6,7-dihydro- ; 6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoléin-5-ium ; Bis[methylenedioxy]protoberberine ; 6H,7H-[1,3]dioxolo[5,4-g][1,3]dioxolo[5'',4'':7,8]isoquino[3,2-a]isoquinolin-5-ium
Product Categories: Alkaloids
CAS NO: 3486-66-6
Molecular Formula:C₁₉H₁₄NO₄
Molecular Weight :320.3182
Molecular Structure :

Coptisine History

Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis). Famous for the bitter taste that it produces, Also found in Greater Celandine and has also been detected in Opium.

Coptisine Uses

Coptisine (CAS NO.3486-66-6) is used in Chinese herbal medicine along with the related compound berberine for treating digestive disorders caused by bacterial infections.

Coptisine Toxicity Data With Reference

orl-rat TDLo:0.1 mg/kg

BIPBU* Biological & pharmaceutical bulletin. 24 (2001),1277.

Coptisine Safety Profile

A poison by ingestion. When Coptisine (CAS NO.3486-66-6) is heated to decomposition it emits toxic vapors of NO_x.

Product Name

COPTISINE

Synthetic route

Coptisine Chemical Properties

Coptisine History

Coptisine Uses

Coptisine Toxicity Data With Reference

Coptisine Safety Profile

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