Lys-MDMA explained
| Width: | 250px |
| Class: | Serotonin–norepinephrine–dopamine releasing agent
- Entactogen; Empathogen
|
| Pubchem: | 166468301 |
| Synonyms: | Lysine-MDMA; N-(L-Lysinamidyl)-3,4-methylenedioxymethamphetamine; N-(L-Lysinamidyl)-MDMA; lysMDMA |
| Iupac Name: | (2S)-2,6-diamino-N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylhexanamide |
| C: | 17 |
| H: | 27 |
| N: | 3 |
| O: | 3 |
| Smiles: | CC(CC1=CC2=C(C=C1)OCO2)N(C)C(=O)[C@H](CCCCN)N |
| Stdinchi: | 1S/C17H27N3O3/c1-12(20(2)17(21)14(19)5-3-4-8-18)9-13-6-7-15-16(10-13)23-11-22-15/h6-7,10,12,14H,3-5,8-9,11,18-19H2,1-2H3/t12?,14-/m0/s1 |
| Stdinchikey: | MJBFXZNNDCEDME-PYMCNQPYSA-N |
Lys-MDMA, or lysine-MDMA, also known as N-(L-lysinamidyl)-MDMA, is a prodrug of MDMA which is being investigated for possible use as a pharmaceutical drug in the treatment of psychiatric disorders.[1] [2] [3] [4] Structurally, lys-MDMA is to MDMA as lisdexamfetamine is to dextroamphetamine As of August 2024, a phase 1 clinical trial comparing MDMA, MDA, lys-MDMA, and lys-MDA has been conducted and completed. Lys-MDMA is being developed by MindMed.
See also
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Notes and References
- Elliott SP, Holdbrook T, Brandt SD . Prodrugs of New Psychoactive Substances (NPS): A New Challenge . Journal of Forensic Sciences . 65 . 3 . 913–920 . May 2020 . 31943218 . 10.1111/1556-4029.14268 . Lisdexamfetamine (N-(1-phenylpropan-2-yl)lysinamide) (Fig. 1A) can be prescribed in the treatment of attention deficit hyperactivity disorder (ADHD) in children and binge eating disorder in adults and consists of dextroamphetamine (d-amphetamine) derivatized with the amino acid L-lysine (11,12). While lisdexamphetamine itself is pharmacologically inactive, in vivo peptidase enzymes associated with red blood cells hydrolyze the amide bond, thereby allowing pharmacological effects being exerted through d-amphetamine (13). The delayed absorption and metabolic profile for formation of the active drug reduces lisdexamfetamine’s abuse liability and increases its safety profile (11,12). However, use of lisdexamfetamine has been mentioned in some Internet user forums as well as lysineMDMA (5,14,15). .
- Synthesis routes to access MDMA prodrugs by using controlled and non-controlled intermediates . US . 11896670 . Trachsel D, Liechti ME, Lustenberger F . Mind Medicine Inc. . 13 February 2024 .
- Web site: (2S)-2,6-diamino-N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylhexanamide ]. PubChem . U.S. National Library of Medicine . 13 November 2024.
- Web site: Mind Medicine (MindMed) . MindMed Collaborators Dose First Patient in Phase 1 Investigator-Initiated Trial of MDMA-Like Substances . PR Newswire . 20 September 2022 . 13 November 2024.
