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| CAS No.: | 3486-66-6 |
|---|---|
| Name: | COPTISINE |
| Article Data: | 6 |
| Molecular Structure: | |
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| Formula: | C19H14 N O4 |
| Molecular Weight: | 320.324 |
| Synonyms: | Berbinium,7,8,13,13a-tetradehydro-2,3:9,10-bis(methylenedioxy)- (8CI); Alkaloid A, fromCoptis groenlandica; Coptisin; Coptisine; YHL II |
| Density: | g/cm3 |
| Melting Point: | 212-217 °C |
| Boiling Point: | °Cat760mmHg |
| Flash Point: | °C |
| Hazard Symbols: | A poison. |
| Risk Codes: | A poison.:; ">  A poison.:; |
| Safety: | A poison by ingestion. When heated to decomposition it emits toxic vapors of NOx. |
| PSA: | 40.80000 |
| LogP: | 2.80780 |
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- 3486-66-6
coptisine
| Conditions | Yield |
|---|---|
| With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h; | 74% |
| Conditions | Yield |
|---|---|
| Multistep reaction; |
| Conditions | Yield |
|---|---|
| With potassium hydroxide In dimethyl sulfoxide at 40 - 90℃; for 5h; Inert atmosphere; |
| 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 | Yield |
|---|---|
| In dimethyl sulfoxide at 115 - 120℃; for 25.5h; |
- 53777-78-9
Dihydrocoptisine
- 3486-66-6
coptisine
| 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 | 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 |
- 3486-66-6
coptisine
| 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 |
- 72744-54-8
5-bromo-benzo[1,3]dioxole-4-carbaldehyde
- 3486-66-6
coptisine
| 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 |
- 3486-66-6
coptisine
| 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 |
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Chemistry
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 :
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.
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.
Toxicity Data With Reference
| 1. | orl-rat TDLo:0.1 mg/kg | BIPBU* Biological & pharmaceutical bulletin. 24 (2001),1277. |
Safety Profile
A poison by ingestion. When Coptisine (CAS NO.3486-66-6) is heated to decomposition it emits toxic vapors of NOx.