Edge Rewrite
restyle Source code View original
// HTMLRewriter · presentation

This page was redesigned at the edge.

Cloudflare fetched the original article and streamed it through HTMLRewriter to apply an entirely new visual system without rebuilding the source page.

Jump to content

UWA-001

Add links
From Wikipedia, the free encyclopedia

UWA-001
Clinical data
Other namesUWA001; α-Phenyl-MDMA; Methylenedioxymephenidine
Drug classSerotonin–norepinephrine reuptake inhibitor; Serotonin 5-HT2 receptor modulator
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.[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

[edit]

References

[edit]
  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.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=UWA-001&oldid=1341027345"