Chemistry:UWA-101

UWA-101
Legal status
Legal status	CA: Schedule I ; UK: Class A ;
Identifiers
	IUPAC name 2-(1,3-Benzodioxol-5-yl)-1-cyclopropyl-N-methylethanamine;
CAS Number	1350821-24-7;
PubChem CID	17756669;
ChemSpider	27444374;
UNII	0N2Q1RYR1X;
ChEMBL	ChEMBL3302434;
Chemical and physical data
Formula	C13H17NO2
Molar mass	219.284 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C3CC3C(NC)Cc2cc1OCOc1cc2;
	InChI InChI=1S/C13H17NO2/c1-14-11(10-3-4-10)6-9-2-5-12-13(7-9)16-8-15-12/h2,5,7,10-11,14H,3-4,6,8H2,1H3; Key:DNROCNZQNQSVOG-UHFFFAOYSA-N;

Short description: Chemical compound

UWA-101 (also known as α-cyclopropyl-MDMA) 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.^[1]^[2]^[3]^[4] 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.^[5]

Replacing the α-methyl with a cyclopropyl dramatically reduces affinity for the noradrenaline transporter and 5-HT_2A 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.^[6] This research was a continuation of earlier work from the same team led by medicinal chemist Matthew Piggott, at the University of Western Australia, 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.^[7]^[8]

UWA-121 is the (R)-enantiomer of UWA-101 and the (S)-enantiomer is UWA-122.^[9] Both are active monoamine reuptake inhibitors.^[9]

Another relative is UWA-104 ("α-isopropyl-MDMA"), which is also active.^[6]

References

↑ "Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect?". Neuroscience Letters 330 (3): 251–4. September 2002. doi:10.1016/s0304-3940(02)00823-6. PMID 12270640.
↑ "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 23 (27): 9107–15. October 2003. doi:10.1523/JNEUROSCI.23-27-09107.2003. PMID 14534244.
↑ "3,4-Methylenedioxymethamphetamine counteracts akinesia enantioselectively in rat rotational behavior and catalepsy". Synapse 55 (3): 148–55. March 2005. doi:10.1002/syn.20102. PMID 15602749.
↑ "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 31 (19): 7190–8. May 2011. doi:10.1523/JNEUROSCI.1171-11.2011. PMID 21562283.
↑ Jerome, Ilsa (Spring 2008). "MDMA and Parkinson's: Lots of Research, Few Practical Answers.". MAPS XVI (1): 16–18. http://www.maps.org/news-letters/v16n1/mdma_parkinsons.pdf. Retrieved 2012-04-09.
↑ ^6.0 ^6.1 "A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances L-DOPA benefit in parkinsonian primates". FASEB Journal 26 (5): 2154–63. May 2012. doi:10.1096/fj.11-195016. PMID 22345403.
↑ "Redesigning the designer drug ecstasy: nonpsychoactive MDMA analogues exhibiting Burkitt's lymphoma cytotoxicity". MedChemComm 1 (4): 287–293. 2010. doi:10.1039/c0md00108b.
↑ "Enhancing the anti-lymphoma potential of 3,4-methylenedioxymethamphetamine ('ecstasy') through iterative chemical redesign: mechanisms and pathways to cell death". Investigational New Drugs 30 (4): 1471–83. August 2012. doi:10.1007/s10637-011-9730-5. PMID 21850491. http://pure-oai.bham.ac.uk/ws/files/10275792/MDMA_Analogues_Wasik_et_al.pdf. Retrieved 2019-09-18.
↑ ^9.0 ^9.1 "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 82: 76–87. July 2014. doi:10.1016/j.neuropharm.2014.01.012. PMID 24447715.

External links

Do neurologists dance? A personal experience of Parkinson's disease & MDMA, Tim Lawrence, 2003

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Original source: https://en.wikipedia.org/wiki/UWA-101. Read more

[1] "Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect?". Neuroscience Letters 330 (3): 251–4. September 2002. doi:10.1016/s0304-3940(02)00823-6. PMID 12270640.

[2] "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 23 (27): 9107–15. October 2003. doi:10.1523/JNEUROSCI.23-27-09107.2003. PMID 14534244.

[3] "3,4-Methylenedioxymethamphetamine counteracts akinesia enantioselectively in rat rotational behavior and catalepsy". Synapse 55 (3): 148–55. March 2005. doi:10.1002/syn.20102. PMID 15602749.

[4] "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 31 (19): 7190–8. May 2011. doi:10.1523/JNEUROSCI.1171-11.2011. PMID 21562283.

[5] Jerome, Ilsa (Spring 2008). "MDMA and Parkinson's: Lots of Research, Few Practical Answers.". MAPS XVI (1): 16–18. http://www.maps.org/news-letters/v16n1/mdma_parkinsons.pdf. Retrieved 2012-04-09.

[JohnstonMillar2012-6] 6.0 ^6.1 "A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances L-DOPA benefit in parkinsonian primates". FASEB Journal 26 (5): 2154–63. May 2012. doi:10.1096/fj.11-195016. PMID 22345403.

[7] "Redesigning the designer drug ecstasy: nonpsychoactive MDMA analogues exhibiting Burkitt's lymphoma cytotoxicity". MedChemComm 1 (4): 287–293. 2010. doi:10.1039/c0md00108b.

[8] "Enhancing the anti-lymphoma potential of 3,4-methylenedioxymethamphetamine ('ecstasy') through iterative chemical redesign: mechanisms and pathways to cell death". Investigational New Drugs 30 (4): 1471–83. August 2012. doi:10.1007/s10637-011-9730-5. PMID 21850491. http://pure-oai.bham.ac.uk/ws/files/10275792/MDMA_Analogues_Wasik_et_al.pdf. Retrieved 2019-09-18.

[HuotJohnston2014-9] 9.0 ^9.1 "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 82: 76–87. July 2014. doi:10.1016/j.neuropharm.2014.01.012. PMID 24447715.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101

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Legal status	CA: Schedule I UK: Class A
Identifiers
IUPAC name 2-(1,3-Benzodioxol-5-yl)-1-cyclopropyl-N-methylethanamine
CAS Number	1350821-24-7
PubChem CID	17756669
ChemSpider	27444374
UNII	0N2Q1RYR1X
ChEMBL	ChEMBL3302434
Chemical and physical data
Formula	C₁₃H₁₇NO₂
Molar mass	219.284 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C3CC3C(NC)Cc2cc1OCOc1cc2
InChI InChI=1S/C13H17NO2/c1-14-11(10-3-4-10)6-9-2-5-12-13(7-9)16-8-15-12/h2,5,7,10-11,14H,3-4,6,8H2,1H3 Key:DNROCNZQNQSVOG-UHFFFAOYSA-N

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