UWA-001

UWA-001
Identifiers
IUPAC name
  • 2-(1,3-benzodioxol-5-yl)-N-methyl-1-phenylethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC16H17NO2
Molar mass255.317 g·mol−1
3D model (JSmol)
SMILES
  • CNC(Cc1ccc2OCOc2c1)c3ccccc3
InChI
  • 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.[1]

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).[1]

Unlike MDMA and para-methoxyamphetamine (but similarly to ketamine),[2] UWA-001 increases prepulse inhibition and was therefore considered to be non-psychoactive, though it was not assayed at other binding sites.[3] It is toxic to the SH-SY5Y cell line at high concentrations, however significantly less toxic than MDMA at all concentrations tested.[3]

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.

See also

References

  1. 1 2 Johnston TH, Millar Z, Huot P, Wagg K, Thiele S, Salomonczyk D, et al. (May 2012). "A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances L-DOPA benefit in parkinsonian primates". FASEB Journal. 26 (5): 2154–63. doi:10.1096/fj.11-195016. PMID 22345403. S2CID 37589231.
  2. ↑ Abel KM, Allin MP, Hemsley DR, Geyer MA (May 2003). "Low dose ketamine increases prepulse inhibition in healthy men". Neuropharmacology. 44 (6): 729–37. doi:10.1016/S0028-3908(03)00073-X. PMID 12681371. S2CID 25706718.
  3. 1 2 Gandy MN, McIldowie M, Lewis K, Wasik AM, Salomonczyk D, Wagg K, et al. (2010). "Redesigning the designer drug ecstasy: non-psychoactive MDMA analogues exhibiting Burkitt's lymphoma cytotoxicity". MedChemComm. 1 (4): 287–93. doi:10.1039/C0MD00108B.
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