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MDO-NPA

Dopaminergic drug From Wikipedia, the free encyclopedia

MDO-NPA (10,11-methylenedioxy-N-n-propylnoraporphine) is a synthetic aporphine derivative used as a research tool in neuropharmacology. It was developed as a methylenedioxy prodrug of N-n-propylnorapomorphine (NPA). A noteworthy advantage that the MDO-NPA congener has over NPA and apomorphine is that MDO-NPA has a high oral bioavailability, whereas the other two do not and must be delivered via subcutaneous injection or intraperitoneally.

CAS Number
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MDO-NPA
Identifiers
  • (12R)-10,11-Methylenedioxy-N-propylnoraporphine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H21NO2
Molar mass307.393 g·mol−1
3D model (JSmol)
  • CCCN1CCC2=C3[C@H]1CC4=C(C3=CC=C2)C5=C(C=C4)OCO5
  • InChI=1S/C20H21NO2/c1-2-9-21-10-8-13-4-3-5-15-18(13)16(21)11-14-6-7-17-20(19(14)15)23-12-22-17/h3-7,16H,2,8-12H2,1H3/t16-/m1/s1
  • Key:YSONYEIWWIFWEV-MRXNPFEDSA-N
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Pharmacology

Pharmacokinetics

In vivo O-dealkylation releases NPA, yielding an orally effective, relatively long-acting dopaminergic agent that acts at central dopamine receptors. Evidence for this prodrug behavior includes blockade of MDO-NPA’s behavioral effects and prevention of NPA formation by the microsomal oxidase inhibitor SKF-525A.[1]

Pharmacodynamics

In animal models, MDO-NPA produces robust dopamine-mediated behavioral effects with “depot-like” properties, and across studies has shown dose-dependent agonist/antagonist interactions and, for certain stereoisomers, limbic-selective actions.[1][2] MDO-NPA exists as two distinct enantiomers. One of these enantiomers is active as a dopamine agonist while the other is active as a dopamine antagonist.[3]

MDO-NPA has not been developed as a therapeutic drug and remains primarily of experimental interest alongside related aporphine congeners.[2]

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