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Substance Name: Caulophylline
RN: 486-86-2
UNII: TT0MW69NCI
InChIKey: CULUKMPMGVXCEI-VHSXEESVSA-N

Note

  • Alkaloid from Sophora flavescens with anthelmintic activity.

Classification Code

  • Drug / Therapeutic Agent

Molecular Formula

  • C12-H16-N2-O

Molecular Weight

  • 204.2714
 
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Names and Synonyms

Name of Substance

  • Caulophylline
  • N-Methylcytisine

Synonyms

  • 1,5-Methano-8H-pyrido(1,2a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-, (1R)-
  • 12-Methylcytisine
  • 5-24-02-00538 (Beilstein Handbook Reference)
  • BRN 0012448
  • Caulophyllin
  • Caulophylline
  • EINECS 207-643-8
  • N-Methylcytisine
  • UNII-TT0MW69NCI

Systematic Names

  • (1R)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one
  • 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-, (1R)-
  • Cytisine, 12-methyl-

Registry Numbers

CAS Registry Number

  • 486-86-2

FDA UNII

  • TT0MW69NCI

System Generated Number

  • 0000486862

Structure Descriptors

InChI

1S/C12H16N2O/c1-13-6-9-5-10(8-13)11-3-2-4-12(15)14(11)7-9/h2-4,9-10H,5-8H2,1H3/t9-,10+/m0/s1

InChIKey

CULUKMPMGVXCEI-VHSXEESVSA-N

Smiles

CN1C[C@@H]2C[C@H](C1)C3=CC=CC(=O)N3C2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 51mg/kg (51mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
British Journal of Pharmacology. Vol. 35, Pg. 161, 1969.
mouse LD50 intravenous 22mg/kg (22mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacology and Experimental Therapeutics. Vol. 79, Pg. 334, 1943.
mouse LD50 oral 511mg/kg (511mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
British Journal of Pharmacology. Vol. 35, Pg. 161, 1969.
mouse LDLo unreported 160mg/kg (160mg/kg)   Journal of Ethnopharmacology. Vol. 7, Pg. 24, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 137 deg C   EXP
log P (octanol-water) 0.810 (none)   EST
Water Solubility 9.09E+05 mg/L   EXP
Atmospheric OH Rate Constant 8.72E-11 cm3/molecule-sec 25 EST

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