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Substance Name: Aconitine [USP]
RN: 302-27-2
UNII: X8YN71D5WC
InChIKey: XFSBVAOIAHNAPC-NPVHKAFCSA-N

Note

  • A C19 norditerpenoid alkaloid (DITERPENES) from the root of ACONITUM plants. It activates VOLTAGE-GATED SODIUM CHANNELS. It has been used to induce ARRHYTHMIAS in experimental animals and it has antiinflammatory and antineuralgic properties.

Molecular Formula

  • C34-H47-N-O11

Molecular Weight

  • 645.7413
 

Classification Codes

  • Adjuvants, Immunologic
  • Human Data
  • Immunologic Factors
  • Membrane Transport Modulators
  • Natural Product
  • Sodium Channel Agonists
  • Voltage-Gated Sodium Channel Agonists
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Names and Synonyms

Name of Substance

  • Aconitine
  • Aconitine [USP]

MeSH Heading

  • Aconitine

Synonyms

  • Aconitin
  • Aconitin cristallisat
  • Aconitin cristallisat [German]
  • Aconitine
  • Aconitinum
  • Aconitysat
  • Akonitin
  • EINECS 206-121-7
  • NSC 56464
  • UNII-X8YN71D5WC

Systematic Names

  • Aconitane-3,8,13,14,15-pentol, 20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)-, 8-acetate 14-benzoate, (1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-
  • Aconitine
  • Aconitine (Crystalline)

Registry Numbers

CAS Registry Number

  • 302-27-2

FDA UNII

  • X8YN71D5WC

System Generated Number

  • 0000302272

Structure Descriptors

InChI

1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20-,21+,22-,23+,24+,25-,26-,27+,28-,29+,31+,32-,33+,34-/m1/s1

InChIKey

XFSBVAOIAHNAPC-NPVHKAFCSA-N

Smiles

CCN1C[C@]2(COC)[C@H](O)C[C@H](OC)[C@@]34[C@@H]5C[C@]6(O)[C@@H](OC)[C@H](O)[C@](OC(=O)C)([C@@H]([C@H](OC)[C@H]23)[C@@H]14)[C@H]5[C@H]6OC(=O)c7ccccc7

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 80ug/kg (0.08mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 324, 1955.
cat LDLo subcutaneous 100ug/kg (0.1mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 873, 1981.
dog LDLo intravenous 350ug/kg (0.35mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1291, 1935.
frog LDLo subcutaneous 586ug/kg (0.586mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1291, 1935.
guinea pig LD50 intravenous 60ug/kg (0.06mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 324, 1955.
guinea pig LDLo subcutaneous 50ug/kg (0.05mg/kg)   Journal of the American Pharmaceutical Association. Vol. 12, Pg. 957, 1923.
human LDLo oral 28mg/kg (28mg/kg) GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 72, 1969.
mouse LD50 intraperitoneal 270ug/kg (0.27mg/kg)   Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 2, Pg. 170, 1981.
mouse LD50 intravenous 100ug/kg (0.1mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
European Journal of Pharmacology. Vol. 337, Pg. 165, 1997.
mouse LD50 oral 1mg/kg (1mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 159, 1982.
mouse LD50 subcutaneous 270ug/kg (0.27mg/kg)   Japanese Journal of Toxicology. Vol. 2, Pg. 225, 1989.
pigeon LDLo subcutaneous 66ug/kg (0.066mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1291, 1935.
rabbit LDLo subcutaneous 131ug/kg (0.131mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1291, 1935.
rat LD50 intravenous 80ug/kg (0.08mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 324, 1955.
rat LDLo intraperitoneal 250ug/kg (0.25mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Proceedings of the Society for Experimental Biology and Medicine. Vol. 26, Pg. 221, 1928.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 204 deg C   EXP
log P (octanol-water) 0.130 (none)   EST
Water Solubility 310 mg/L 25 EXP
Vapor Pressure 1.38E-20 mm Hg 25 EST
Henry's Law Constant 4.53E-26 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.84E-10 cm3/molecule-sec 25 EST

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