A8001

Aconitine

≥95% (HPLC), crystalline

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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300 + H330
• Precautionary Statements: P260 - P264 - P271 - P284 - P304 + P340 + P310 - P403 + P233
• 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