2589-47-1 Usage
Originator
Neo-Gilurtymal, Giulini ,W. Germany,1973
Manufacturing Process
1 g of ajmaline was dissolved in 4 cc of chloroform, and 1 cc of allyl bromidewas added to the resulting solution. The reaction mixture thus obtained was allowed to stand for 24 hours at room temperature. Thereafter, the clear reaction solution was briefly cooled to a temperature below 0°C, whereby crystallization set in. The crystals were filtered off and were then recrystallized from a mixture of absolute methanol and absolute ether. The purified colorless crystalline product was identified to be N-(b)-allyl-ajmalinium-bromide having a melting point of 252°C to 254°C.75 g of N-(b)-n-propyl-ajmalinium-bromide were suspended in 3 liters of an aqueous saturated solution of sodium bicarbonate, and the suspension was admixed with 3 liters of chloroform. The resulting mixture was vigorously stirred for six to eight hours. Thereafter, the chloroform phase was separated and evaporated to dryness. 68 g of a yellow syrup remained as a residue. The aldehyde base was dissolved in about 150 cc of acetone and, while stirring and cooling on an ice bath, the solution was slowly admixed with a solution of 25 g of tartaric acid in 2 liters of acetone. The fine white precipitate formed thereby was separated by vacuum filtration, washed with ether and dried. The raw product, weighing 80 g, was recrystallized once from a mixture of ethanol and ether, yielding 50 g of N-(b)-n-propyl-ajmalinium hydrogen tartrate having a melting point of 149°C to 152°C (decomposition).
Therapeutic Function
Antiarrhythmic
Safety Profile
Poison by ingestion and
intravenous routes. An experimental
teratogen. Human systemic effects by
ingestion: hallucinations and distorted
perceptions. Experimental reproductive
effects. An antiarrhythmic agent. When
heated to decomposition it emits toxic
fumes of NOx
Check Digit Verification of cas no
The CAS Registry Mumber 2589-47-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,8 and 9 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2589-47:
(6*2)+(5*5)+(4*8)+(3*9)+(2*4)+(1*7)=111
111 % 10 = 1
So 2589-47-1 is a valid CAS Registry Number.
InChI:InChI=1/C23H33N2O2.C4H6O6/c1-4-10-25-17-11-14(13(5-2)22(25)27)19-18(25)12-23(21(19)26)15-8-6-7-9-16(15)24(3)20(17)23;5-1(3(7)8)2(6)4(9)10/h6-9,13-14,17-22,26-27H,4-5,10-12H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/q+1;/p-1/t13-,14-,17-,18-,19?,20-,21+,22+,23+,25?;1-,2-/m01/s1
2589-47-1Relevant articles and documents
The structure of the ring-opened N(β)-propyl-ajmaline (Neo- Gilurytmal) at physiological pH is obviously responsible for its better absorption and bioavailability when compared with ajmaline (Gilurytmal)
Hinse,Stoeckigt, Joachim
, p. 531 - 532 (2007/10/03)
Prajmaline, the semisynthetic propyl derivative of ajmaline, shows a much better bioavailability when compared with the Rauvolfia alkaloid ajmaline. Early NMR and IR-studies, fluorescence spectroscopic investigations and extraction experiments combined with ion-pair chromatography proved the thesis of a tautomeric equilibrium between an aldehyde-amine and a quaternary carbinol-ammonium component. The aim of this study was to confirm this thesis by HPLC-separation and by structure-determination of both tautomeric compounds.
