3DChem.com - Chemistry, Structures & 3D Molecules a visual and interactive website showcasing the beautiful world of chemistry

Levodopa (Molecule of the Month for October 2016)

L-DOPA



Levodopa or L-DOPA is an intermediate in dopamine biosynthesis. Clinically, levodopa is used in the management of Parkinson's disease.

Levodopa is used as a prodrug to increase dopamine levels for the treatment of Parkinson's disease, since it is able to cross the blood-brain barrier whereas dopamine itself cannot. Once levodopa has entered the central nervous system (CNS), it is metabolized to dopamine by aromatic-L-amino-acid decarboxylase. However, conversion to dopamine also occurs in the peripheral tissues, causing adverse effects and decreasing the available dopamine to the CNS, so it is standard practice to co-administer a peripheral DOPA decarboxylase inhibitor.

In work that earned him a Nobel Prize in 2000, Swedish scientist Arvid Carlsson first showed in the 1950s that administering levodopa to animals with Parkinsonian symptoms would cause a reduction of the symptoms. The 2001 Nobel Prize in Chemistry was also related to L-DOPA: the Nobel Committee awarded one-fourth of the prize to William S. Knowles for his work on chirally catalysed hydrogenation reactions, the most noted example of which was used for the synthesis of L-DOPA.

Formal Chemical Name (IUPAC)
(S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

References

http://en.wikipedia.org/wiki/L-DOPA

Picture of Levodopa

click on the picture above to interact
with the 3D model of the
Levodopa structure
(this will open a new browser window)

Picture of Levodopa

C9H11NO4



Update by Karl Harrison
(Molecule of the Month for October 2016 )