Ajmaline

Ajmaline
Clinical data
Trade names	Gilurytmal, Ritmos, Aritmina
AHFS/Drugs.com	International Drug Names
ATC code	C01BA05 (WHO) ;
Identifiers
	IUPAC name (17R,21R)-ajmalan-17,21-diol; OR; (1R,9R,10S,13R,14R,16S,18S)- 13-ethyl- 8-methyl- 8,15-diazahexacyclo [14.2.1.01,9.02,7.010,15.012,17] nonadeca- 2(7),3,5-triene- 14,18-diol;
CAS Number	4360-12-7 ;
PubChem CID	20367;
DrugBank	DB01426 ;
ChemSpider	10469368 ;
UNII	1PON08459R;
KEGG	D00199 ;
ChEMBL	ChEMBL1230919 ;
CompTox Dashboard (EPA)	DTXSID6045537 ;
ECHA InfoCard	100.022.219
Chemical and physical data
Formula	C20H26N2O2
Molar mass	326.440 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@H]1[C@H]5C[C@@H]4N([C@@H]1O)[C@H]6C[C@]3(c2ccccc2N(C)[C@H]34)[C@H](O)C56;
	InChI InChI=1S/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 ; Key:CJDRUOGAGYHKKD-SXKXKDIKSA-N ;
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Ajmaline (also known by trade names Gilurytmal, Ritmos, and Aritmina) is an alkaloid that is classified as a 1-A antiarrhythmic agent. It is often used to induce arrhythmic contraction in patients suspected of having Brugada syndrome. Individuals suffering from Brugada syndrome will be more susceptible to the arrhythmogenic effects of the drug, and this can be observed on an electrocardiogram as an ST elevation.

The compound was first isolated by Salimuzzaman Siddiqui in 1931 ^[1] from the roots of Rauvolfia serpentina. He named it ajmaline, after Hakim Ajmal Khan, one of the most illustrious practitioners of Unani medicine in South Asia.^[2] Ajmaline can be found in most species of the genus Rauvolfia as well as Catharanthus roseus.^[3] In addition to Southeast Asia, Rauvolfia species have also been found in tropical regions of India, Africa, South America, and some oceanic islands. Other indole alkaloids found in Rauvolfia include reserpine, ajmalicine, serpentine, corynanthine, and yohimbine. While 86 alkaloids have been discovered throughout Rauvolfia vomitoria, ajmaline is mainly isolated from the stem bark and roots of the plant.^[3]

Due to the low bioavailability of ajmaline, a semisynthetic propyl derivative called prajmaline (trade name Neo-gilurythmal) was developed that induces similar effects to its predecessor but has better bioavailability and absorption.^[4]

^ Siddiqui S, Siddiqui RH (1931). "Chemical examination of the roots of Rauwolfia serpentina Benth". J. Indian Chem. Soc. 8: 667–80.
^ Sandilvi AN (12 April 2003). "Salimuzzaman Siddiqui: pioneer of scientific research in Pakistan". Daily Dawn. Archived from the original on 2007-09-27.
^ ^a ^b Roberts MF, Wink M (1998). Alkaloids: Biochemistry, Ecology, and Medical applications. Plenum Press.
^ Hinse C, Stöckigt J (July 2000). "The structure of the ring-opened N beta-propyl-ajmaline (Neo-Gilurytmal) at physiological pH is obviously responsible for its better absorption and bioavailability when compared with ajmaline (Gilurytmal)". Die Pharmazie. 55 (7): 531–532. PMID 10944783.

[1] Siddiqui S, Siddiqui RH (1931). "Chemical examination of the roots of Rauwolfia serpentina Benth". J. Indian Chem. Soc. 8: 667–80.

[sandilvi-2] Sandilvi AN (12 April 2003). "Salimuzzaman Siddiqui: pioneer of scientific research in Pakistan". Daily Dawn. Archived from the original on 2007-09-27.

[Alkaloids-3] Roberts MF, Wink M (1998). Alkaloids: Biochemistry, Ecology, and Medical applications. Plenum Press.

[Neo-gilurythman-4] Hinse C, Stöckigt J (July 2000). "The structure of the ring-opened N beta-propyl-ajmaline (Neo-Gilurytmal) at physiological pH is obviously responsible for its better absorption and bioavailability when compared with ajmaline (Gilurytmal)". Die Pharmazie. 55 (7): 531–532. PMID 10944783.

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