It:Dihydroartemisinin
Abstract
Dihydroartemisinin is the active ingredient in the anti-malarial drugs Alaxin and Cotexin. The parasitic disease is transferred through mosquito bites & in many cases fatal and over the years has become more and more resistant to drugs designed to counter its effects. The disease is most present in tropical countries such as Brazil, India, Thailand and Nigeria due to the the high mosquito population.
Basic Information
| It:Dihydroartemisinin | |
|---|---|
 | |
| General | |
| Systematic name | Dihydroartemisinin |
| Other names | Dihydro-Qinghaosu |
| Molecular formula | C15H24O5 |
| Molar mass | 284.35 g/mol |
| Appearance | White Crystalline Solid |
| CAS number | 81496-82-4 |
| Properties | |
| Melting point | 164-165°C (377-378 K) |
| Related compounds | Sulfadoxine-pyrimethamine |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Dihydroartemisinin is produced by the reduction of Artemisinin (this reaction is covered later). Artemisinin is obtained from the Artemisia annua shrub which has long been used in traditional Chinese medicine. Not all shrubs of this species contain artemisinin. Apparently it is only produced when the plant is subjected to certain conditions. It can be synthesized from arteminisic acid.
3D Image
H1 NMR Spectrum
Synthesis
The image below shows the synthesis of Dihydroartemisinin from Artemisinin using NaBH4:
So how does it actually work?
Although the specific reaction mechanism is not well understood it is known how the malarial parasite is killed. The parasite attacks red blood cells and consumes haemoglobin and producing heme (an iron-based complex). The iron in heme reacts with the peroxide on the Dihydroartemisinin generating high-valent iron-oxo species. Further reactions occur that produce reactive oxygen radicals which damage the parasite leading to its death.
->Heme
References & Useful Links
http://www.buyreagents.com/dihydroartemisinin.html
http://en.wikipedia.org/wiki/Artemisinin
Synthesis Diagram: Immunodetection of Artemisinin in Artemisia Annua Cultivated in Hydroponic Conditions; Journal; Jaziri, Mondher; Diallo, Billo; Vanhaelen, Maurice; Homes, Jacques; Yoshimatsu, Kayo; Shimomura, Koichiro; PYTCAS; Phytochemistry; EN; 33; 4; 1993; 821-826