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lannaconitine

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lannaconitine Basic information

Product Name:
lannaconitine
Synonyms:
  • (1a,14a,16b)-20-Ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-(2-acetylamino)benzoate)
  • (1α,14α,16β)-20-Ethyl-1,14,16-trimethoxyaconitane-
  • 4,8,9-triol4-[2-(acetylamino)benzoate]
  • Aconitane-4,8,9-triol, 20-ethyl-1,14,16-trimethoxy-, 4-(2-acetylamino)benzoate, (1-alpha,14-alpha,16-beta)
  • 20-Ethyl-1α,14α,16β-trimethoxyaconitane 4,8,9-triol 4-[2-(acetylamino)benzoate]
  • 20-Ethyl-1α,14α,16β-trimethoxyaconitane-4,8,9-triol 4-[2-(acetylamino)benzoate]
  • N-Acetylpuberanidine
  • Lannaconitine
CAS:
32854-75-4
MF:
C32H44N2O8
MW:
584.7
Product Categories:
  • Inhibitors
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
Mol File:
32854-75-4.mol
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lannaconitine Chemical Properties

Melting point:
217-218°
alpha 
D18 +27° (chloroform)
Boiling point:
641.72°C (rough estimate)
Density 
1.1897 (rough estimate)
refractive index 
1.6260 (estimate)
storage temp. 
Store at 2-8°C, protect from light
solubility 
Chloroform: 30 mg/ml
form 
A solid
pka
12.55±0.70(Predicted)
Stability:
Hygroscopic
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Safety Information

Toxicity
LD50 in mice (mg/kg): 6.9 i.v.; 9.1 i.p.; approx 20 orally (Dybing)
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lannaconitine Usage And Synthesis

Description

A highly toxic aconitine alkaloid present in Aconitum leucostomum and A. septentrionale Koelle, lappaconitine crystallizes in hexagonal tablets for whichtwo melting points have been recorded. It has [α]D + 22.3° (C6H6) or [α]18D + 27.0° (CHC1 3). The early view that a methylimino group is present has been shown to be erroneous. No crystalline salts are known but the diacetyl derivative forms colourless crystals, m.p. l25-7°C. The base is only sparingly soluble in H20 and most organic solvents, but dissolves readily in CHC1 3.
Boiling the alkaloid with dilute H2S04 in a stream of H2 yields acetic acid and anthranoyllappaconine, C30H4207N2, which forms colourless rhombic tablets, m.p. 146-9°C;[α]25D + 22.07° (C6H6), giving a platinichloride tetrahydrate as brown needles, m.p. 300-31 O°C (dec.). When hydrolyzed with HCl, the base furnishes acetic and anthranilic acids and lappaconine, m.p. 96°C; [α]25D + 22.41°, giving a crystalline hydrochloride, m.p. 246-7°C and the aurichloride monohydrate, m.p. l26-7°C. Alkaline hydrolysis, on the other hand, furnishes lappaconine and lappaconitic acid (acetylanthranilic acid). From these observations, it is clear that only one hydroxyl group is associated with an acyl group in the molecule.
Pharmacologically, lappaconitine is toxic although its action is less pronounced than that of aconitine (q.v.). Toxic doses produce respiratory paralysis and have a direct action upon the heart often terminating in ventricular fibrillation.

Uses

(+)-Lappaconitine is a potential antitumor agent agent that induces HL-60 differentiation and apoptosis with analgesic activity as well.

References

Schultze, Ulfert., Arch. Pharrn., 260,230 (1922)
Weidemann., Chern. Zentr., 1,603 (1923)
Khaimova et al., Tetrahedron Lett., 2711 (1964)
Structure:
Tel'nov, Yunusov, Yunusov., Khirn. Prir. Soedin., 6, 583 (1970)
Pharmacology:
Rosendahl., quoted by Boehm,!. BioI. Chern., 170,203 (1947)

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