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Substance Name: Sanguinarine
RN: 2447-54-3
UNII: AV9VK043SS
InChIKey: INVGWHRKADIJHF-UHFFFAOYSA-N

Note

  • Bactericidal produces glaucoma in laboratory animals; a phytogenic antineoplastic agent; from Argemonemexicana & Sanguinaria; inhibits glutamate decarboxylase.

Molecular Formula

  • C20-H14-N-O4

Molecular Weight

  • 332.3336
 

Classification Codes

  • Anti-Infective Agents
  • Cardiotonic Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Natural Product
  • Protective Agents
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Names and Synonyms

Name of Substance

  • Sanguinarine

Synonyms

  • BRN 3915507
  • Dimethylenedioxy benzphenanthridine
  • EINECS 219-503-3
  • Pseudochelerythrine
  • Sangrovit
  • Sanguinarin
  • Sanguinarine
  • Sanguinarium
  • UI5
  • UNII-AV9VK043SS

Systematic Names

  • (1,3)-Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl- (9CI)
  • Sanguinarine

Registry Numbers

CAS Registry Number

  • 2447-54-3

FDA UNII

  • AV9VK043SS

Other Registry Numbers

  • 1265889-92-6
  • 18203-15-1
  • 857014-91-6

Related Registry Numbers

  • 4752-86-7 (nitrate)
  • 5578-73-4 (chloride)

System Generated Number

  • 0002447543

Structure Descriptors

InChI

1S/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

InChIKey

INVGWHRKADIJHF-UHFFFAOYSA-N

Smiles

C[n+]1cc2c3OCOc3ccc2c4ccc5cc6OCOc6cc5c14

Toxicity

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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 266 deg C   EXP
log P (octanol-water) 2.650 (none)   EST
Atmospheric OH Rate Constant 2.15E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.