UWA-001
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]
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Formula | C16H17NO2 |
Molar mass | 255.31 g/mol g·mol−1 |
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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
- AD-1211
- Diphenidine
- MBDP (UWA-091)
- Methoxphenidine
- MT-45
- UWA-101
References
- Tom H. Johnston; Zak Millar; Philippe Huot; Keith Wagg‖; Sherri Thiele; Danielle Salomonczyk; Christopher J. Yong-Kee; Michael N. Gandy; Matthew McIldowie; Katie D. Lewis; Jordi Gomez-Ramirez; Joohyung Lee; Susan H. Fox; Mathew Martin-Iverson; Joanne E. Nash; Matthew J. Piggott; Jonathan M. Brotchie (May 2012). "A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances l-DOPA benefit in parkinsonian primates". The FASEB Journal. 26 (5): 2154–2163. doi:10.1096/fj.11-195016. PMID 22345403.
- Kathryn M. Abel; Matthew P.G. Allin; David R Hemsley; Mark A. Geyer (May 2013). "Low dose ketamine increases prepulse inhibition in healthy men". Neuropharmacology. 44 (6): 729–737. doi:10.1016/S0028-3908(03)00073-X. PMID 12681371.
- Michael N. Gandy; Matthew McIldowie; Katie Lewis; Agata M. Wasik; Danielle Salomonczyk; Keith Wagg; Zak A. Millar; David Tindiglia; Philippe Huot; Tom Johnston; Sherri Thiele; Blake Nguyen; Nicholas M. Barnes; Jonathan M. Brotchie; Mathew T. Martin-Iverson; Joanne Nash; John Gordon; Matthew J. Piggott (2010). "Redesigning the designer drug ecstasy: non-psychoactive MDMA analogues exhibiting Burkitt's lymphoma cytotoxicity". Medicinal Chemical Communications. 1 (4): 287–293. doi:10.1039/C0MD00108B.
Phenethylamines |
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Amphetamines |
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Cathinones |
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Phenylisobutylamines | |
Phenylalkylpyrrolidines | |
Catecholamines (and close relatives) |
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Miscellaneous |
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