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AJMALINE

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AJMALINE Basic information

Product Name:
AJMALINE
Synonyms:
  • AJMALAN-17,21-DIOL,(17R,21)-
  • AJMALINE
  • 21-diol,(17r,21-alpha)-ajmalan-1
  • 5H-6,10:11,12a-Dimethanoindolo[3,2-b]quinolizine, ajmalan-17,21-diol deriv.
  • Ajmalan-17,20-diol
  • Ajmalan-17,21-diol
  • Ajmalan-17,21-diol, (17R,21alpha)-
  • Ajmalin
CAS:
4360-12-7
MF:
C20H26N2O2
MW:
326.43
EINECS:
224-439-4
Product Categories:
  • Alkaloids
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
4360-12-7.mol
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AJMALINE Chemical Properties

Melting point:
189°C
alpha 
D18 +131° (c = 0.4 in chloroform); D20 +144° (c = 0.8 in chloroform)
Boiling point:
464.47°C (rough estimate)
Density 
1.1117 (rough estimate)
refractive index 
1.6800 (estimate)
storage temp. 
2-8°C
pka
pKa 8.2 (Uncertain)
Water Solubility 
489.7mg/L(30 ºC)
Merck 
13,194
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Safety Information

Hazard Codes 
Xn
Risk Statements 
25-20/21/22
Safety Statements 
13-45-36
RIDADR 
1544
RTECS 
AX8050000
HazardClass 
6.1(b)
PackingGroup 
III
Toxicity
LD50 oral in rat: 360mg/kg
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AJMALINE Usage And Synthesis

Chemical Properties

White Solid

Originator

Ajmaline ,Solvay Pharma

Uses

An antiarrhythmic agent isolated from Rauwolfia serpentina.

Uses

For use as an antiarrhythmic agent.

Definition

ChEBI: A monoterpenoid indole alkaloid that consists of ajmalan substituted at positions 17 and 21 by hydroxy groups.

Manufacturing Process

Ajmaline isolated from Rauwolfia sp. roots: Rauwolfia serpentine Benth., Rauwolfia vomitoria Afr., Rauwolfia canescens L.
Threshed roots of Rauwolfia canescens L. extracted with 5% solution of acetic acid at room temperature for 24 h. Then extract was decanted to flask. This extract was alkalified with ammonia (alkaloid salts were converted to alkaloid bases). The obtained thus method solution was extracted with chloroform 3 or more times. Then chloroform extract was chromatographed on column through Al2O3 sorbent. After chromatography ajmalin was obtained, which had melting point at 205°C (recyrstallization from methanol).

Therapeutic Function

Antiarrhythmic

Purification Methods

Ajmaline crystallises from MeOH or EtOAc containing a little H2O to give the trihydrate m 158-160o. This loses 1H2O at 110o and all H2O at 150o. [Beilstein 23 III/IV 3212.]

AJMALINESupplier

J & K SCIENTIFIC LTD.
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