PROFILBARU.COM

Lys-MDMA
Clinical data
Other names	Lysine-MDMA; N-(L-Lysinamidyl)-3,4-methylenedioxymethamphetamine; N-(L-Lysinamidyl)-MDMA; lysMDMA
Drug class	Serotonin–norepinephrine–dopamine releasing agent; Entactogen; Empathogen
Identifiers
	IUPAC name (2S)-2,6-diamino-N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylhexanamide;
PubChem CID	166468301;
Chemical and physical data
Formula	C17H27N3O3
Molar mass	321.421 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC2=C(C=C1)OCO2)N(C)C(=O)[C@H](CCCCN)N;
	InChI InChI=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; Key: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]^[5] Structurally, lys-MDMA is to MDMA as lisdexamfetamine is to dextroamphetamine^[4]^[3] As of August 2024, a phase 1 clinical trial comparing MDMA, MDA, lys-MDMA, and lys-MDA has been conducted and completed.^[1]^[2]^[5] Lys-MDMA is being developed by MindMed.^[2]^[5]

References

^ ^a ^b Elliott SP, Holdbrook T, Brandt SD (May 2020). "Prodrugs of New Psychoactive Substances (NPS): A New Challenge" (PDF). Journal of Forensic Sciences. 65 (3): 913–920. doi:10.1111/1556-4029.14268. PMID 31943218. 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).
^ ^a ^b ^c Clinical trial number NCT04847206 for "Effects of MDMA-like Substances in Healthy Subjects (MDMA-like)" at ClinicalTrials.gov
^ ^a ^b US 11896670, Trachsel D, Liechti ME, Lustenberger F, "Synthesis routes to access MDMA prodrugs by using controlled and non-controlled intermediates", issued 13 February 2024, assigned to Mind Medicine Inc.
^ ^a ^b "(2S)-2,6-diamino-N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylhexanamide". PubChem. U.S. National Library of Medicine. Retrieved 13 November 2024.
^ ^a ^b ^c Mind Medicine (MindMed) (20 September 2022). "MindMed Collaborators Dose First Patient in Phase 1 Investigator-Initiated Trial of MDMA-Like Substances". PR Newswire. Retrieved 13 November 2024.

External links

Lysine-MDMA - Isomer Design

This psychoactive drug-related article is a stub. You can help Wikipedia by expanding it.

[ElliottHoldbrookBrandt2020-1] Elliott SP, Holdbrook T, Brandt SD (May 2020). "Prodrugs of New Psychoactive Substances (NPS): A New Challenge" (PDF). Journal of Forensic Sciences. 65 (3): 913–920. doi:10.1111/1556-4029.14268. PMID 31943218. 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).

[NCT04847206-2] Clinical trial number NCT04847206 for "Effects of MDMA-like Substances in Healthy Subjects (MDMA-like)" at ClinicalTrials.gov

[US11896670B2-3] US 11896670, Trachsel D, Liechti ME, Lustenberger F, "Synthesis routes to access MDMA prodrugs by using controlled and non-controlled intermediates", issued 13 February 2024, assigned to Mind Medicine Inc.

[PubChem-4] "(2S)-2,6-diamino-N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylhexanamide". PubChem. U.S. National Library of Medicine. Retrieved 13 November 2024.

[MindMed2022-5] Mind Medicine (MindMed) (20 September 2022). "MindMed Collaborators Dose First Patient in Phase 1 Investigator-Initiated Trial of MDMA-Like Substances". PR Newswire. Retrieved 13 November 2024.

[1]

[2]

[3]

[4]

[5]

Lys-MDMA

See also

References

External links