Lys-MDMA

Lys-MDMA, or lysine-MDMA, also known as N-(L-lysinamidyl)-MDMA, is an intended prodrug of MDMA which was being investigated for possible use as a pharmaceutical drug in the treatment of psychiatric disorders.^{[2][3][4][5][6]} Structurally, lys-MDMA is to MDMA as lisdexamfetamine is to dextroamphetamine^[5][4] As of August 2024, a phase 1 clinical trial comparing MDMA, MDA, lys-MDMA, and lys-MDA has been conducted and completed.^[2][3][6] Lys-MDMA was being developed by MindMed.^[3][6]

Lys-MDMA

Clinical data
Other names	Lysine-MDMA; N-(L-Lysinamidyl)-3,4-methylenedioxymethamphetamine; N-(L-Lysinamidyl)-MDMA; lysMDMA
Drug class	Inactive[1]
ATC code	None
Identifiers
IUPAC name (2S)-2,6-diamino-N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylhexanamide
CAS Number	2763054-67-5 Y
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

The published phase 1 clinical trial unexpectedly found that lys-MDMA does not convert into MDMA in humans and is completely inactive.^[1] This is in contrast to lisdexamfetamine and lys-MDA, where are converted into dextroamphetamine and MDA, respectively.^[1] The lack of conversion was attributed to steric hindrance caused by the N-methyl group of lys-MDMA.^[1]

See also

• Substituted methylenedioxyphenethylamine
• Lys-MDA
• Lisdexamfetamine
• DA-Phen
• Phenatine
• MiHKAL