4360-12-7 Usage
Description
Ajmaline, also known as Rauwolfia serpentina, is a monoterpenoid indole alkaloid derived from the Rauwolfia plant. It is characterized by its white or yellowish crystal powder appearance and has a melting point of 205-207°C. Ajmaline exhibits optical rotation of +144° in chloroform and is well soluble in organic solvents such as methanol and ethanol, while being slightly soluble in water. It is typically stored at a temperature of 2-8°C. Rauwolfia has been used in traditional Chinese medicine for various ailments, including cold, fever, sore throat, headache, dizziness caused by hypertension, abdominal pain, diarrhea, scabies, and venomous snake bites.
Uses
Used in Pharmaceutical Industry:
Ajmaline is used as an antiarrhythmic agent for the treatment of abnormal heart rhythms. It is particularly effective in managing atrial and ventricular arrhythmias, helping to stabilize the heart's electrical activity and maintain a regular heartbeat.
Used in Traditional Chinese Medicine:
Ajmaline is used as a medicinal component in traditional Chinese medicine for the treatment of various conditions such as cold, fever, sore throat, headache, dizziness caused by hypertension, abdominal pain, diarrhea, scabies, and venomous snake bites. Its diverse applications in traditional medicine make it a valuable resource for treating a wide range of ailments.
Used in Drug Delivery Systems:
Ajmaline's chemical properties, such as its solubility in organic solvents and slight solubility in water, make it a suitable candidate for drug delivery systems. These systems can be designed to improve the bioavailability, delivery, and therapeutic outcomes of Ajmaline, enhancing its effectiveness in treating various conditions.
Originator
Ajmaline ,Solvay Pharma
History
Since 1930s, abundant studies have been focused on the Rauwolfia plants. So far, a
total of 91 alkaloids were separated from Rauwolfia, and the identification of the
chemical structures was obtained, including 2 non-indole alkaloids (thebaine and
papaverine) and 89 indole alkaloids . In accordance with the basic framework,
indole alkaloids can be divided into seven classes, such as the ajmaline class, the
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
Pharmacology
Anti-arrhythmic
R. serpentina (She Geng Mu) is the first anti-arrhythmic herbal medicine in the
psychiatry history. Ajmaline has a potent anti-arrhythmic effect for treating atrial and ventricular arrhythmias and also has a good effect on the treatment of
Wolff-Parkinson-White syndrome. Ajmaline plays a main role in decreasing the
permeability of sodium ion on the myocardial cell membrane by moderately inhibiting the sodium channel. The electrophysiological effect of ajmaline is similar to that
of quinidine, but it is stronger than quinidine.
In addition, ajmaline has a mild anti-sympathetic effect. It affects sympathetic
nerve endings to release more sodium, dilate the coronary artery, relax vascular
smooth muscle, and then decrease blood pressure. Therefore, it is suitable for clinical treatment of atrial and ventricular premature beats, pre-excitation syndrome
with supraventricular tachycardia, but not suitable for the treatment of paroxysmal
atrial fibrillation and sinus tachycardia.
Clinical Use
Ajmaline has the anti-arrhythmic effects for the treatment of atrial or ventricular
extrasystoles, paroxysmal supraventricular or ventricular tachycardia, and paroxysmal atrial fibrillation. The lethal dose for human ranged from 100 to 500?mg/kg.
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.]
References
Le Gall., Ann. ph arm. franc., 18,817 (1960)
Check Digit Verification of cas no
The CAS Registry Mumber 4360-12-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,6 and 0 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 4360-12:
(6*4)+(5*3)+(4*6)+(3*0)+(2*1)+(1*2)=67
67 % 10 = 7
So 4360-12-7 is a valid CAS Registry Number.
InChI:InChI=1/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11+,14-,15-,16?,17-,18+,19+,20+/m0/s1
4360-12-7Relevant articles and documents
SYNTHESIS OF IRIDODIAL BY CELL FREE EXTRACTS FROM RAUWOLFIA SERPENTINA CELL SUSPENSION CULTURES
Uesato, Shinichi,Ogawa, Yasuko,Inouye, Hiroyuki,Saiki, Kayoko,Zenk, Meinhart H.
, p. 2893 - 2896 (2007/10/02)
The cell free extracts of Rauwolfia serpentina cell suspension cultures converted 10-hydroxygeraniol/ 10-hydroxynerol into iridodial in the presence of oxidized and reduced pyridine nucleotides.However, neither 10-hydroxycitronellol nor 9,10-dihydroxygera