Carmicheline

Base Information

• Chemical Name: Carmicheline
• CAS No.: 39089-30-0
• Molecular Formula: C₂₂H₃₅NO₄
• Molecular Weight: 377.524
• DSSTox Substance ID: DTXSID20959905
• Wikidata: Q27107081
• Metabolomics Workbench ID: 53240
• Mol file: 39089-30-0.mol

Synonyms:Karakoline;Carmicheline;Karacoline;Carmichaeline;39089-30-0;Aconitane-1,8,14-triol, 20-ethyl-16-methoxy-4-methyl-, (1-alpha,14-alpha,16-beta)-;20-ethyl-16beta-methoxy-4-methylaconitane-1alpha,8,14alpha-triol;CHEBI:6113;DTXSID20959905;C08693;Q27107081;(1S,2R,3R,4S,5S,6S,8S,9S,13R,16S,17R)-11-ethyl-6-methoxy-13-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8,16-triol

Chemical Property of Carmicheline

Chemical Property:

• Vapor Pressure: 6.38E-14mmHg at 25°C
• Melting Point: 185-186℃ (acetone )
• Boiling Point: 540.2°Cat760mmHg
• PKA: 13.80±0.70(Predicted)
• Flash Point: 280.5°C
• PSA: 73.16000
• Density: 1.3g/cm³
• LogP: 1.18850
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 377.25660860
• Heavy Atom Count: 27
• Complexity: 673

Purity/Quality:

99%+, ^*data from raw suppliers

Karacoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CC2(CCC(C34C2CC(C31)C5(CC(C6CC4C5C6O)OC)O)O)C
• Isomeric SMILES: CCN1C[C@@]2(CC[C@@H]([C@@]34[C@@H]2C[C@@H](C31)[C@]5(C[C@@H]([C@H]6C[C@@H]4[C@@H]5[C@H]6O)OC)O)O)C
• Description: A second atisine base found in the tubers of Aconitum karacolicum, the structure has been elucidated from chemical and spectroscopic data. Oxidation with KMn04 gives anhydroepoxykaracoline. The alkaloid furnishes a triacetyl deriva_x0002_tive which, after pyrolysis and hydrolysis, yields acetyldemethylisopyrokaracoline.
• Uses: Karacoline is an Aconitane (A189875) derivative, which is a neurotoxin which 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.