2H-12,3,6a-Ethanylylidene-7,9-methanonaphth[2,3-b]azocine, aconitane-3,8,13,14,15-pentol deriv.

Base Information

• Chemical Name: 2H-12,3,6a-Ethanylylidene-7,9-methanonaphth[2,3-b]azocine, aconitane-3,8,13,14,15-pentol deriv.
• CAS No.: 302-27-2
• Molecular Formula: C34H47NO11
• Molecular Weight: 645.747
• European Community (EC) Number: 206-121-7
• Wikipedia: Aconitine
• Wikidata: Q105327247
• NCI Thesaurus Code: C87421
• Mol file: 302-27-2.mol

Synonyms:Acetylbenzoyl aconine;Acetylbenzoyl-aconine;Acetylbenzoylaconine;Aconitane-3,8,13,14,15-pentol, 20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)-, 8-acetate 14-benzoate, (1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-;Aconitine

Chemical Property of 2H-12,3,6a-Ethanylylidene-7,9-methanonaphth[2,3-b]azocine, aconitane-3,8,13,14,15-pentol deriv.

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 200-205 °C (dec.)
• Refractive Index: 1.614
• Boiling Point: 717.2 °C at 760 mmHg
• PKA: 5.88(at 25℃)
• Flash Point: 387.6 °C
• PSA: 153.45000
• Density: 1.37 g/cm³
• LogP: 0.58600
• Storage Temp.: Refrigerator
• Water Solubility.: Soluble in ethanol. Sparingly soluble in water
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 645.31491132
• Heavy Atom Count: 46
• Complexity: 1210

Purity/Quality:

Aconitine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,Xi
• Hazard Codes: T+,Xi
• Statements: 26/28-36/37/38
• Safety Statements: 24-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1CC2(C(CC(C34C2C(C(C31)C5(C6C4CC(C6OC(=O)C7=CC=CC=C7)(C(C5O)OC)O)OC(=O)C)OC)OC)O)COC
• Description: Aconitum plants (Wu Tou, Ranunculaceae family) have been widely used to treat various diseases, such as rheumatism, knee pain, herpes zoster, scabies, and other disorders in China for thousands of years. It was first described in Shen Nong’s Herbal Classic (the earliest classical work of Chinese herbs). Aconitine is the main active component in Aconitum plants.
• Physical properties: Appearance: solid. Solubility: barely soluble in water and soluble in organic solvents such as chloroform or diethyl ether. Its solubility in water and ethanol are 0.3?mg/mL and 35?mg/mL, respectively. Melting point: 203–204?°C (397–399?°F; 476–477?K). Optical rotation:D+17.3°
• Uses: Aconitine occurs to the extent of 0.4–0.8%in dried tuberous roots of aconite or monkshood (Aconitum napellus L. and Ranunculaceae) found in India, North America,and Europe. It is used to produce heartarrhythmia in experimental animals and asan antipyretic agent. anesthetic (gastric), antipyretic, and cardiotoxin Neurotoxin. Activates tetrodotoxin-sensitive Na+ channels, inducing presynaptic depolarization, thus blocking the nerve action potential which, in turn, blocks the release of neurotransmitters and dec reases the end plate potential at the neuromuscular junction. Aconitine also blocks norepinephrine reuptake. In the heart, aconitine induces ventricular tachycardia after intracoronary injection. In c ultured ventricular myocytes, aconitine increases the duration of the action potential and induces the appearance of early after depolarization. Used in producing heart arrhythmia in experimental anim als.
• Indications: Aconitine was previously used as an antipyretic and analgesic. However, the clinical application of aconitine is limited by its high toxicity. Its lethal dose 50% (LD50) for mice is 1.8?mg/kg (orally) and 0.308?mg/kg (intraperitoneally).
• Clinical Use: In clinic, it can be used for treating and alleviating the symptoms caused by arthritis, lumbocrural pain, and herpes zoster; however, it is utilized infrequently in clinical practice due to its obvious side effectsAccording to a review of different reports of aconite poisoning in human beings, the following clinical features such as neurological, cardiovascular, and gastrointestinal features were observed. The first symptom of aconitine poisoning appeared approximately 20?min–2?h after oral intake, and they were paresthesia, sweating, and nausea, which led to severe vomiting, colicky diarrhea, intense pain, and then paralysis of the skeletal muscles. Following the onset of life-threatening arrhythmia, including ventricular tachycardia and ventricular fibrillation, death finally occurred as a result of respiratory paralysis or cardiac arrest.

Technology Process of 2H-12,3,6a-Ethanylylidene-7,9-methanonaphth[2,3-b]azocine, aconitane-3,8,13,14,15-pentol deriv.

There total 2 articles about 2H-12,3,6a-Ethanylylidene-7,9-methanonaphth[2,3-b]azocine, aconitane-3,8,13,14,15-pentol deriv. which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 12.0%

C34H45NO11 (639-24-7) → indaconitine (302-27-2,140188-61-0) + aconitine

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 12h;

DOI:10.1080/10286020.2012.684684

Reference yield:

→ Aconitin (302-27-2,140188-61-0)

Guidance literature:

Synth. in d. Reihe v.- u. Delphinin;

DOI:10.1139/v69-397

Reference yield: 44.0%

azelaic acid (123-99-9,26776-28-3) + indaconitine (302-27-2,140188-61-0) → 8-O-(14-benzoylaconine) azelate + bis[O-(14-benzoylaconin-8-yl)] azelate (1227799-59-8)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 7h;

DOI:10.1016/j.ejmech.2012.05.015

upstream raw materials:

C₃₄H₄₅NO₁₁

Downstream raw materials:

aconitine oxynitride

3,13,15-triacetylaconitine

Aconine

(16R)-20-ethyl-14α-benzoyloxy-3α,13-dihydroxy-1α,6α,16-trimethoxy-4-methoxymethyl-aconitan-15-one

Refernces