Pseudoaconitine
INDACONITINE · pseudoaconitine · 8-Acetyl ludaconitine · acetylveratrylpseudoaconine · acetyl benzoylpseudo-aconine · (16S)-20-Ethyl-1α,6α,16-trimethoxy-4-methoxymethylaconitane-3α,8,13,14α-tetrol 8-acetate 14-(3,4-dimethoxybenzoate) · Aconitane-3,8,13,14-tetrol, 20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)-, 8-acetate 14-(3,4-dimethoxybenzoate), (1α,3α,6α,14α,16β)-
Identifikatoren & physikalische Daten
| CAS No. | 127-29-7 |
|---|---|
| Summenformel | C36H51NO12 |
| Durchschnittliche Molmasse | 689,799 g/mol |
| Monoisotopische Masse | 689,34112607 g/mol |
| SMILES | CCN1C[C@]2(COC)[C@H](O)C[C@H](OC)[C@@]34[C@@H]5C[C@]6(O)[C@@H](OC)C[C@@](OC(C)=O)([C@H]5[C@H]6OC(=O)c5ccc(OC)c(OC)c5)[C@@H]([C@H](OC)[C@H]23)[C@@H]14 |
| InChIKey | YVPYMQHYESYLIR-HZKWNRCISA-N |
| PubChem CID | 90478913 |
| DTXSID | DTXSID90894011 |
Chemische & physikalische Eigenschaften
| Schmelzpunkt | 214° |
|---|---|
| Siedepunkt | 697.88°C (rough estimate) |
| Dichte | 1.2083 (rough estimate) |
| Brechungsindex | 1.6630 (estimate) |
| pKa (Säurekonstante) | 12+-.0.70(Predicted) |
Anwendungen & Verwendung
Beschreibung
An aconitine alkaloid obtained from A coniturn chasrnanthurn Stapf. by Dunstan and Andrews, the base crystallizes from EtOH as hexagonal prisms or rosettes of fine needles. It has [α]20Do + IS.3° (EtOH) and gives a series of crystalline salts, e.g. the hydrobromide as hexagonal prisms from H20, m.p. lS3-7°C; [edo - 17.3° or as crystals from EtOH or Et 20, m.p. 217 -SoC and the aurichloride, yellow needles, m.p. 147 -152°C with sintering at 142°C. Indaconitine resembles Aconitine (q. v.) in giving a crystalline precipitate with KMn04 but in this case the crystals are markedly smaller. Four methoxyl groups are present and when the SUlphate is heated in aqueous solution in a sealed tube it furnishes acetic acid and benzoylpseudaconine (Indbenzaconine), as a colourless glass, m.p. 130-3°C; [α]D + 33.6° (EtOH), also giving crystalline salts: hydrochloride, m.p. 242-4°C; [α]D - S.Oo (H 20); hydrobromide as the dihydrate, m.p. 247°C (dry) and the aurichloride, rosettes of orange needles, m.p. 180-2°C. Alkaline hydrolysis gives acetic and benzoic acids and pseudaconine, C2sH4108N. On pyrolysis, the alkaloid loses one mole of acetic acid with the formation of a-pyroindaconitine which is amorphous, m.p. 130-2°C; [α]D + 91.9° (EtOH), giving a crystalline hydro bromide, m.p. 194-SoC. When inda_x0002_conitine hydrochloride is subjected to the same treatment it yields the isomeric ~-pyroindaconitine, also amorphous, but furnishing a crystalline hydrobromide, m.p. 24S-250°C; [α]D + 27.6°.
Verwenden
8-Acetyl ludaconitine occurs in the tubers of Indianaconite (bish or Aconitum ferox), found inIndia and Nepal. It is used in arrow poisoningfor hunting. Clinically, it is used in treatingrheumatism.