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Key Documents

A8001

Sigma-Aldrich

Aconitine

≥95% (HPLC), crystalline

Synonyme(s) :

Acetylbenzoylaconine

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About This Item

Formule empirique (notation de Hill):
C34H47NO11
Numéro CAS:
Poids moléculaire :
645.74
Numéro Beilstein :
74608
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Pureté

≥95% (HPLC)

Forme

crystalline

Couleur

white

Solubilité

H2O: 0.3 mg/mL
ethanol: 35 mg/mL

Chaîne SMILES 

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

Clé InChI

XFSBVAOIAHNAPC-VBUFWTEXSA-N

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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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbones

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

Acute Tox. 1 Oral - Acute Tox. 2 Inhalation

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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


Certificats d'analyse (COA)

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Les clients ont également consulté

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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
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)
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
Na Li et al.
Planta medica, 78(7), 692-697 (2012-03-14)
Aconitine (AC), mesaconitine (MA), and hypaconitine (HA) are the active alkaloids identified in aconite tuber, an important traditional Chinese medicine. The study is aimed to investigate their intestinal transport profiles and potential interaction during the intestinal absorption using the Caco-2
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

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