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A8001

Sigma-Aldrich

Aconitine

≥95% (HPLC), crystalline

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Synonym(s):
Acetylbenzoylaconine
Empirical Formula (Hill Notation):
C34H47NO11
CAS Number:
Molecular Weight:
645.74
Beilstein:
74608
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥95% (HPLC)

form

crystalline

color

white

solubility

H2O: 0.3 mg/mL
ethanol: 35 mg/mL

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

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

InChI key

XFSBVAOIAHNAPC-VBUFWTEXSA-N

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This Item
40771044787C4382
Aconitine ≥95% (HPLC), crystalline

A8001

Aconitine

Sigma-Aldrich

407710

α-Iodoacetamide

Aconitine analytical standard

44787

Aconitine

Carbamoylcholine chloride ≥98% (titration), crystalline

C4382

Carbamoylcholine chloride

form

crystalline

form

crystalline solid

form

-

form

crystalline

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

solubility

H2O: 0.3 mg/mL, ethanol: 35 mg/mL

solubility

methanol: 1:20, DMF: soluble, ethanol: soluble, water: soluble

solubility

-

solubility

H2O: 1 g/mL, ethanol: 20 mg/mL

color

white

color

white

color

-

color

white

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Inhalation

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Peijian Tong et al.
Journal of ethnopharmacology, 146(2), 562-571 (2013-02-05)
Fuzi (lateral root of Aconitum carmichaeli) is a popular traditional Chinese medicine well known for its both therapeutic and high-toxic activities. Its toxic alkaloid ingredients, mainly aconitine, mesaconitine, and hypaconitine, are responsible for the high toxicity. However, to date, no
A Ameri
Progress in neurobiology, 56(2), 211-235 (1998-10-07)
Preparations of Aconitum roots are employed in Chinese and Japanese medicine for analgesic, antirheumatic and neurological indications. The recent surge in use of phytomedicine derived from traditional Chinese medicine as well as increasing concerns about possible toxic effects of these
Bio-analytical studies on the process of detoxification and safety evaluation of Aconitum laciniatum and Abrus precatorius for use in ayurvedic preparations
Bapat, S P and Sane, R T
International Journal of Pharmaceutical Sciences and Research, 3(3), 914-914 (2012)
Ling Ye et al.
Toxicology letters, 216(2-3), 86-99 (2012-12-04)
Aconitum alkaloids including aconitine (AC), mesaconitine (MA), hypaconitine (HA), are highly toxic. Their hydrolysates, such as benzoylaconine (BAC), benzoylmesaconine (BMA), benzoylhypaconine (BHA), aconine, and mesaconine, are considerably less toxic. Efflux transporters, including P-glycoprotein (P-gp), breast cancer resistance protein (BCRP), and
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

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