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Sanguinarine

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Name

Sanguinarine

EINECS 219-503-3
CAS No. 2447-54-3 Density 1.3463 (rough estimate)
PSA 40.80000 LogP 3.42810
Solubility N/A Melting Point 205-215 °C
Formula C20H14NO4 Boiling Point 483.53°C (rough estimate)
Molecular Weight 332.335 Flash Point N/A
Transport Information UN 1544 Appearance N/A
Safety 13-45 Risk Codes 25
Molecular Structure Molecular Structure of 2447-54-3 (SANGUINARINE) Hazard Symbols N/A
Synonyms

Sanguinarine(8CI);Pseudochelerythrine;Sanguinarium;

Article Data 6

Sanguinarine Specification

The (1,3)-Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl- (9CI), with the formula C20H14NO4, is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. The systematic name of this chemical is 13-methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium. With the CAS registry number 2447-54-3 and EINECS 219-503-3, it is also named as Sanguinarine. The product's category is Alkaloids. It kills cells and may destroy tissue if applied to the skin. What's more, this chemical is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. And it is synthesized from dihydrosanguinarine through the action of Dihydrobenzophenanthridine oxidase in plants.

The other characteristics of (1,3)-Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl- (9CI) can be summarized as: (1)XLogP3-AA: 4.4; (2)H-Bond Donor: 0; (3)H-Bond Acceptor: 4; (4)Rotatable Bond Count: 0; (5)Exact Mass: 332.092283; (6)MonoIsotopic Mass: 332.092283; (7)Topological Polar Surface Area: 40.8; (8)Heavy Atom Count: 25; (9)Formal Charge: 1; (10)Complexity: 530; (11)Isotope Atom Count: 0; (12)Covalently-Bonded Unit Count: 1.

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed, so people should keep it away from food, drink and animal foodstuffs. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure. 
1. SMILES:O1c3c(OC1)c2c[n+](c5c(c2cc3)ccc6cc4OCOc4cc56)C
2. InChI:InChI=1/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
3. InChIKey:INVGWHRKADIJHF-UHFFFAOYAZ

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous 120mg/kg (120mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
dog LD50 subcutaneous 70mg/kg (70mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
frog LD50 subcutaneous 70mg/kg (70mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
mouse LD50 intraperitoneal 18mg/kg (18mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 195, 1982.
mouse LD50 intravenous 19400ug/kg (19.4mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Farmakologiya i Toksikologiya Vol. 29, Pg. 76, 1966.
mouse LD50 subcutaneous 80mg/kg (80mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
rabbit LD50 subcutaneous 125mg/kg (125mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
rat LC50 inhalation 2200gm/m3 (2200000mg/m3)   Toxicologist. Vol. 5, Pg. 176, 1985.
rat LD50 intraperitoneal 18mg/kg (18mg/kg)   Indian Journal of Cancer. Vol. 5, Pg. 183, 1968.
rat LD50 intravenous 28700ug/kg (28.7mg/kg)   Toxicologist. Vol. 5, Pg. 176, 1985.
rat LD50 oral 1660mg/kg (1660mg/kg)   Toxicologist. Vol. 5, Pg. 176, 1985.

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