Surf Wiki
Save to docs
general/methylenedioxyphenethylamines

From Surf Wiki (app.surf) — the open knowledge base

UWA-101

Chemical compound

Chemical compound

| elimination_half-life =

UWA-101, also known as α-cyclopropyl-3,4-methylenedioxyphenethylamine (α-cPr-MDPEA), is a phenethylamine derivative 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 side-effects of Parkinson's disease therapy, most notably levodopa-induced dyskinesia. However the illegal status of MDMA and concerns about its potential for recreational use, 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, 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, while retaining similar or slightly improved antidyskinetic effectiveness when compared to MDMA.

UWA-121 is the (R)-enantiomer of UWA-101 and the (S)-enantiomer is UWA-122. Both are active monoamine reuptake inhibitors. UWA-121 is an SDRI with 10-fold preference for inhibition of dopamine reuptake over serotonin reuptake while UWA-122 is a highly selective serotonin reuptake inhibitor.

Another relative is UWA-104 ("α-isopropyl-MDMA"), which is also active. It is a selective dopamine reuptake inhibitor, with greater than 30-fold selectivity over the other monoamine transporters or the serotonin 5-HT2A receptor. Other analogues include UWA-091 ("α-propyl-MDMA"), UWA-102 ("α-tert-butyl-MDMA"), and UWA-001 ("α-phenyl-MDMA"). The in vitro pharmacological activities of UWA-101, UWA-104, and UWA-001 have been reported.

References

References

  1. (September 2002). "Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect?". Neuroscience Letters.
  2. (October 2003). "3,4-methylenedioxymethamphetamine (ecstasy) inhibits dyskinesia expression and normalizes motor activity in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated primates". The Journal of Neuroscience.
  3. (March 2005). "3,4-Methylenedioxymethamphetamine counteracts akinesia enantioselectively in rat rotational behavior and catalepsy". Synapse.
  4. (May 2011). "Characterization of 3,4-methylenedioxymethamphetamine (MDMA) enantiomers in vitro and in the MPTP-lesioned primate: R-MDMA reduces severity of dyskinesia, whereas S-MDMA extends duration of ON-time". The Journal of Neuroscience.
  5. Jerome, Ilsa. (Spring 2008). "MDMA and Parkinson's: Lots of Research, Few Practical Answers.". MAPS.
  6. (2010). "Redesigning the designer drug ecstasy: nonpsychoactive MDMA analogues exhibiting Burkitt's lymphoma cytotoxicity". MedChemComm.
  7. (August 2012). "Enhancing the anti-lymphoma potential of 3,4-methylenedioxymethamphetamine ('ecstasy') through iterative chemical redesign: mechanisms and pathways to cell death". Investigational New Drugs.
  8. (July 2014). "UWA-121, a mixed dopamine and serotonin re-uptake inhibitor, enhances L-DOPA anti-parkinsonian action without worsening dyskinesia or psychosis-like behaviours in the MPTP-lesioned common marmoset". Neuropharmacology.
  9. (May 2012). "A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances L-DOPA benefit in parkinsonian primates". FASEB Journal.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

methylenedioxyphenethylamines serotonin–dopamine-reuptake-inhibitors substituted-amphetamines
Want to explore this topic further?

Ask Mako anything about UWA-101 — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report