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O,O′-Diacetyldopamine
Experimental dopamine prodrug From Wikipedia, the free encyclopedia
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O,O′-Diacetyldopamine, or 3,4-O-diacetyldopamine, also known as 3,4-diacetoxyphenethylamine, is a synthetic derivative of dopamine in which both of the hydroxyl groups have been acetylated.[1][2][3][4]
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The drug was an attempt at creating a more lipophilic analogue and prodrug of dopamine which could potentially be used medically for central nervous system indications like treatment of Parkinson's disease.[1][2][3][4]
Dopamine itself is too hydrophilic to cross the blood–brain barrier and hence is peripherally selective.[1][2] This, in part, prevents dopamine itself from being employed pharmaceutically for such uses.[1][2] Whereas the experimental log P of dopamine is -0.98,[5] the predicted log P (XLogP3) of O,O′-diacetyldopamine is 0.3.[6] The optimal log P for brain permeation and central activity is about 2.1 (range 1.5–2.7).[7][8]
O,O′-Diacetyldopamine proved to be inactive in animal behavioral tests.[1][4] This suggests that dopamine O-acetylation alone is insufficient to allow for brain permeability.[1][4] However, synthetic dopamine derivatives that were both O-acetylated and N-alkylated, with further increased lipophilicity, for instance N,N-dimethyl-O,O′-acetyldopamine (XLogP3 = 1.3),[9] were robustly active in behavioral tests, including reversal of behavioral depression induced by the dopamine depleting agent tetrabenazine.[4]
Other dopamine analogues and prodrugs have also been developed and studied.[1][10][11][12]
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