Lys-MDMA

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

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[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.

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v t e Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA DMMDA DMMDA-2 EIDA Lys-MDA MDEA MDMA (midomafetamine) (R)-MDMA MDMOH MDOH MMDA MMDA-2 MMDMA N-t-BOC-MDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MAPBT 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB IBF5MAP Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-CMC 3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

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 Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 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 ZDCM-04 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 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 Venlafaxine

See also

References

External links