UWA-001

UWA-001
Identifiers
  • 2-(1,3-benzodioxol-5-yl)-N-methyl-1-phenylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H17NO2
Molar mass255.317 g·mol−1
3D model (JSmol)
  • CNC(Cc1ccc2OCOc2c1)c3ccccc3
  • InChI=1S/C16H17NO2/c1-17-14(13-5-3-2-4-6-13)9-12-7-8-15-16(10-12)19-11-18-15/h2-8,10,14,17H,9,11H2,1H3
  • Key:DNOTUUOUOFJQJC-UHFFFAOYSA-N

UWA-001 (also known as α-phenyl-MDMA and methylenedioxymephenidine) is a phenethylamine derivative invented at the University of Western Australia as non-toxic alternative to 3,4-methylenedioxy-N-methylamphetamine (MDMA) and researched as a potential treatment for Parkinson's disease.

It has a 5-HT2A receptor affinity of 1.2 μM (~10-fold increase compared to MDMA), 1.3 μM for the serotonin transporter (~4-fold decrease compared to MDMA), 13.4 μM for the norepinephrine transporter (~26-fold increase compared to MDMA) and virtually no affinity for the dopamine transporter (>50 μM).

Unlike MDMA and para-methoxyamphetamine (but similarly to ketamine), UWA-001 increases prepulse inhibition and was therefore considered to be non-psychoactive, though it was not assayed at other binding sites. It is toxic to the SH-SY5Y cell line at high concentrations, however significantly less toxic than MDMA at all concentrations tested.

UWA-001 is structurally related to the diarylethylamines lefetamine (a stimulant and opioid) and the dissociative anesthetic ephenidine, which acts as a NMDA receptor antagonist.

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