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Merck

A8001

Aconitine

≥95% (HPLC), fibronectin binding Inhibitor , crystalline

Synonym(s):

Acetylbenzoylaconine

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About This Item

Empirical Formula (Hill Notation):
C34H47NO11
CAS Number:
302-27-2
Molecular Weight:
645.74
NACRES:
NA.77
PubChem Substance ID:
24891304
UNSPSC Code:
12352200
EC Number:
206-121-7
MDL number:
MFCD00082375
Beilstein/REAXYS Number:
74608

Key Documents

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Product Name

Aconitine, ≥95% (HPLC), crystalline

InChI key

XFSBVAOIAHNAPC-VBUFWTEXSA-N

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

SMILES string

CCN1C[C@]2(COC)[C@H](O)C[C@@H](OC)C34C5C[C@]6(O)[C@@H](OC)[C@H](O)[C@@](OC(C)=O)(C5[C@H]6OC(=O)c7ccccc7)C([C@H](OC)C23)C14

assay

≥95% (HPLC)

form

crystalline

color

white

solubility

H2O: 0.3 mg/mL
ethanol: 35 mg/mL

Quality Level

200

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Application

Aconitine has been used:
  • to study its cardiotoxic effects along the pericardium meridian (PM) on cardiac rhythm in rabbits
  • as a standard in high-performance thin layer chromatography (HPTLC) fingerprinting method
  • in the aconitine-based lipo-alkaloids semi-synthesis

Aconitine is a neurotoxin which activates tetrodotoxin-sensitive Na+ channels, inducing presynaptic depolarization and blocking the release of neurotransmitters. Aconitine also blocks norepinephrine reuptake. In the heart, aconitine induces ventricular tachycardia after intracoronary injection.

Biochem/physiol Actions

Aconitine is a diesterditerpene alkaloid found abundantly in the plant Aconitum genera. It possesses analgesic, antipyretic and antirheumatic activity. Aconitine is involved in blocking neurotransmission. It acts as a neurotoxin as well as a cardiotoxin. Aconitine triggers ventricular tachycardia (VT) and ventricular fibrillation (VF). It interacts with voltage-dependent Na+ channels which results in the depolarization of membranes. Aconitine may exhibit therapeutic effects against systemic lupus erythematosus (SLE). It also inhibits the reuptake of norepinephrine.
Neurotoxin. Activates tetrodotoxin-sensitive Na+ channels, inducing presynaptic depolarization, thus blocking the nerve action potential which, in turn, blocks the release of neurotransmitters and decreases the end plate potential at the neuromuscular junction. Aconitine also blocks norepinephrine reuptake. In the heart, aconitine induces ventricular tachycardia after intracoronary injection. In cultured ventricular myocytes, aconitine increases the duration of the action potential and induces the appearance of early after depolarization.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Inhalation

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000521659
0000521658
0000521660
0000521658
0000521659

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Hongbin Zhu et al.
Talanta, 103, 56-65 (2012-12-04)
A fingerprinting approach was developed by means of UPLC-ESI/MS(n) (ultra-performance liquid chromatography-electrospray ionization/mass spectrometry) for the quality control of processed Radix Aconiti, a widely used toxic traditional herbal medicine. The present fingerprinting approach was based on the two processing methods
T Sawanobori et al.
Japanese heart journal, 37(5), 709-718 (1996-09-01)
The effects of antiarrhythmic agents, including Classes I and IV and 3-10 mM Mg2+ on aconitine-induced arrhythmias were examined using a conventional microelectrode and patch clamp method in Langendorff-perfused rabbit hearts and isolated guinea-pig ventricular myocytes. Intracoronary application of 0.1
Hong-Fei Zhang et al.
Analytica chimica acta, 724, 54-60 (2012-04-10)
A magnetic carbon nanomaterial for Fe(3)O(4) enclosure hydroxylated multi-walled carbon nanotubes (Fe(3)O(4)-EC-MWCNTs-OH) was prepared by the aggregating effect of Fe(3)O(4) nanoparticle on MWCNTs-OH, and combined with high-performance liquid chromatography (HPLC)/diode array detection (DAD) to determine the aconitines (aconitine, hypaconitine and
Aconitine
Natural Small Molecule Drugs from Plants, 349-352 (2018)
Hongbin Zhu et al.
Analytica chimica acta, 752, 69-77 (2012-10-30)
This study presents a novel and rapid method to identify chemical markers for the quality control of Radix Aconiti Preparata, a world widely used traditional herbal medicine. In the method, the samples with a fast extraction procedure were analyzed using
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