Samiksha Jaiswal (Editor)

UWA 101

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CAS Number
  
1350821-24-7

UNII
  
0N2Q1RYR1X

3D model (Jmol)
  
Interactive image

Pubchem
  
17756669

ChemSpider ID
  
27444374

PubChem CID
  
17756669

Formula
  
C13H17NO2

Molar mass
  
219.279 g/mol

ChEMBL ID
  
3302434

UWA-101 uploadwikimediaorgwikipediacommonsccbUWA10

Legal status
  
CA: Schedule I UK: Class A

UWA-101 (also known as α-cyclopropyl-MDMA) is a phenethylamine derivative invented at the University of Western Australia and researched as a potential treatment for Parkinson's disease. Its chemical structure is very similar to that of the illegal drug MDMA, the only difference being the replacement of the α-methyl group with an α-cyclopropyl group. MDMA has been found in animal studies and reported in unauthorised human self-experiments to be effective in the short-term relief of Parkinson's disease symptoms, especially when used alongside conventional treatment with L-DOPA. However the illegal status of MDMA and concerns about its abuse potential, neurotoxicity and potentially dangerous side effects mean that it is unlikely to be investigated for medical use in this application, and so alternative analogues were investigated.

Replacing the α-methyl with a cyclopropyl dramatically reduces affinity for the noradrenaline transporter and 5-HT2A receptor targets, while retaining high serotonin transporter affinity and markedly increasing affinity for the dopamine transporter (and as such, it is one of the few selective SDRIs or serotonin-dopamine reuptake inhibitors). This change causes UWA-101 to lack cytotoxicity and MDMA-like behavioral effects in animals, but while retaining similar or slightly improved anti-Parkinsonian effectiveness when compared to MDMA. This research was a continuation of earlier work from the same team which showed that replacing the α-methyl group of MDMA with larger aromatic ring systems produced compounds which lacked psychoactivity and neurotoxicity, but had potent anti-cancer effects against Burkitt's lymphoma cells in vitro.

UWA-121 is the (R)-enantiomer of UWA-101 and the (S)-enantiomer is UWA-122. Both are active monoamine reuptake inhibitors.

Another relative is UWA-104 ("α-isopropyl-MDMA"), which is also active.

References

UWA-101 Wikipedia