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Merck

A8001

Aconitine

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

Sinónimos:

Acetylbenzoylaconine

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Fórmula empírica (notación de Hill):
C34H47NO11
Número CAS:
302-27-2
Peso molecular:
645.74
NACRES:
NA.77
PubChem Substance ID:
24891304
UNSPSC Code:
12352200
EC Number:
206-121-7
MDL number:
MFCD00082375
Beilstein/REAXYS Number:
74608

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Nombre del producto

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

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000521659
0000521658
0000521660
0000521658
0000521659

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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
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
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
Yu-hong Zhou et al.
International journal of medical sciences, 10(9), 1242-1249 (2013-08-13)
Aconitine is a well-known arrhythmogenic toxin and induces triggered activities through cardiac voltage-gated Na(+) channels. However, the effects of aconitine on intracellular Ca(2+) signals were previously unknown. We investigated the effects of aconitine on intracellular Ca(2+) signals in rat ventricular
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Product Information Sheet - A8001

Product Information Sheet

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