| Identification | Back Directory | [Name]
KARAKOLINE | [CAS]
39089-30-0 | [Synonyms]
Karacoline
Carmicheline(7CI)
(16S)-20-Ethyl-16-methoxy-4-methylaconitane-1α,8,14α-triol
Aconitane-1,8,14-triol,20-ethyl-16-methoxy-4-methyl-, (1a,14a,16b)-
Aconitane-1,8,14-triol, 20-ethyl-16-methoxy-4-methyl-, (1α,14α,16β)-
11aH-12,3,6a-Ethanylylidene-7,9-methanonaphth[2,3-b]azocine, aconitane-1,8,14-triolderiv. | [Molecular Formula]
C22H35NO4 | [MDL Number]
MFCD00285963 | [MOL File]
39089-30-0.mol | [Molecular Weight]
377.522 |
| Chemical Properties | Back Directory | [Melting point ]
185-186℃ (acetone ) | [Boiling point ]
540.2±50.0 °C(Predicted) | [density ]
1.30±0.1 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
2-8°C | [form ]
Solid | [pka]
13.80±0.70(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [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. | [Definition]
ChEBI: An organonitrogen heterocyclic compound that is aconitane bearing hydroxy groups at the 1alpha, 8, and 14alpha positions and substituted at on the nitrogen and at positions 4 and 16beta by ethyl, methyl, a
d methoxy groups, respectively. | [References]
Sultankhodzhaev, Yunusov, Yunusov., Khim. Prir. Soedin., 9, 199 (1973) |
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