Lys-MDMA

Last updated
Lys-MDMA
Lys-MDMA structure.png
Clinical data
Other namesLysine-MDMA; N-(L-Lysinamidyl)-3,4-methylenedioxymethamphetamine; N-(L-Lysinamidyl)-MDMA; lysMDMA
Drug class Serotonin–norepinephrine–dopamine releasing agent; Entactogen; Empathogen
Identifiers
  • (2S)-2,6-diamino-N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylhexanamide
CAS Number
PubChem CID
Chemical and physical data
Formula C17H27N3O3
Molar mass 321.421 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCO2)N(C)C(=O)[C@H](CCCCN)N
  • 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]

Contents

See also

Related Research Articles

<span class="mw-page-title-main">Amphetamine</span> Central nervous system stimulant

Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity; it is also used to treat binge eating disorder in the form of its inactive prodrug lisdexamfetamine. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.

<span class="mw-page-title-main">MDMA</span> Psychoactive drug, often called ecstasy

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy, and molly, is an empathogen–entactogenic drug with stimulant and minor psychedelic properties. In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.

A psychiatric or psychotropic medication is a psychoactive drug taken to exert an effect on the chemical makeup of the brain and nervous system. Thus, these medications are used to treat mental illnesses. These medications are typically made of synthetic chemical compounds and are usually prescribed in psychiatric settings, potentially involuntarily during commitment. Since the mid-20th century, such medications have been leading treatments for a broad range of mental disorders and have decreased the need for long-term hospitalization, thereby lowering the cost of mental health care. The recidivism or rehospitalization of the mentally ill is at a high rate in many countries, and the reasons for the relapses are under research.

<span class="mw-page-title-main">Stimulant</span> Drug that increases alertness

Stimulants are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, mood, and physical performance. Some stimulants occur naturally, while others are exclusively synthetic. Common stimulants include caffeine, nicotine, amphetamines, cocaine, methylphenidate, and modafinil. Stimulants may be subject to varying forms of regulation, or outright prohibition, depending on jurisdiction.

<span class="mw-page-title-main">Dextroamphetamine</span> CNS stimulant and isomer of amphetamine

Dextroamphetamine is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is primarily prescribed for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It has also been used illicitly to enhance cognitive and athletic performance, as well as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.

<span class="mw-page-title-main">Adderall</span> Drug mixture used mainly to treat ADHD and narcolepsy

Adderall and Mydayis are trade names for a combination drug containing four salts of amphetamine. The mixture is composed of equal parts racemic amphetamine and dextroamphetamine, which produces a (3:1) ratio between dextroamphetamine and levoamphetamine, the two enantiomers of amphetamine. Both enantiomers are stimulants, but differ enough to give Adderall an effects profile distinct from those of racemic amphetamine or dextroamphetamine, which are marketed as Evekeo and Dexedrine/Zenzedi, respectively. Adderall is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used illicitly as an athletic performance enhancer, cognitive enhancer, appetite suppressant, and recreationally as a euphoriant. It is a central nervous system (CNS) stimulant of the phenethylamine class.

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as sass, is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<span class="mw-page-title-main">Lisdexamfetamine</span> Central nervous system stimulant prodrug

Lisdexamfetamine, sold under the brand names Vyvanse and Elvanse among others, is a stimulant medication that is used to treat attention deficit hyperactivity disorder (ADHD) in children and adults and for moderate-to-severe binge eating disorder in adults. Lisdexamfetamine is taken by mouth. Its effects generally begin within two hours and last for up to 14 hours.

<span class="mw-page-title-main">Substituted methylenedioxyphenethylamine</span> Class of psychoactive drugs

The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational substances.

<span class="mw-page-title-main">3,4-Methylenedioxyphentermine</span> Chemical compound

3,4-Methylenedioxyphentermine (MDPH) is a lesser-known drug of the amphetamine family. MDPH was first synthesized by Alexander Shulgin. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDPH.

<span class="mw-page-title-main">Phenylpropylaminopentane</span> Stimulant drug of the substituted phenethylamine class

1-Phenyl-2-propylaminopentane is an experimental drug related to selegiline which acts as a catecholaminergic activity enhancer (CAE).

<span class="mw-page-title-main">Levoamphetamine</span> CNS stimulant and isomer of amphetamine

Levoamphetamine is a stimulant medication which is used in the treatment of certain medical conditions. It was previously marketed by itself under the brand name Cydril, but is now available only in combination with dextroamphetamine in varying ratios under brand names like Adderall and Evekeo. The drug is known to increase wakefulness and concentration in association with decreased appetite and fatigue. Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries. Levoamphetamine is taken by mouth.

<span class="mw-page-title-main">MDAI</span> Chemical compound

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.

<span class="mw-page-title-main">Norepinephrine releasing agent</span> Catecholaminergic type of drug

A norepinephrine releasing agent (NRA), also known as an adrenergic releasing agent, is a catecholaminergic type of drug that induces the release of norepinephrine (noradrenaline) and epinephrine (adrenaline) from the pre-synaptic neuron into the synapse. This in turn leads to increased extracellular concentrations of norepinephrine and epinephrine therefore an increase in adrenergic neurotransmission.

Substituted amphetamines, or simply amphetamines, are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

<span class="mw-page-title-main">5-MAPB</span> Chemical compound

5-MAPB, also known as 5-(N-methyl-2-aminopropyl)benzofuran, is an entactogen and designer drug of the amphetamine family that is similar to MDMA in its structure and effects.

Amphetamine type stimulants (ATS) are a group of synthetic drugs that are chemical derivatives of the parent compound alpha-methylphenethylamine, also known as amphetamine. Common ATS includes amphetamine, methamphetamine, ephedrine, pseudoephedrine, 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxyethylamphetamine (MDEA). ATS when used illicitly has street names including ice, meth, crystal, crank, bennies, and speed. Within the group of amphetamine-type stimulants, there are also prescription drugs including mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine.

<span class="mw-page-title-main">Lys-MDA</span> Chemical compound

Lys-MDA is a substituted amphetamine derivative with empathogenic effects, which acts as a prodrug for MDA with a slower onset of effects and longer duration of action. Lys-MDA, along with the related derivative Lys-MDMA, are in early stage human clinical trials as potential treatments for treatment-resistant depression and post-traumatic stress disorder. New MDMA prodrugs are in the development phase at MiHKAL GmbH in Switzerland. A phase 1 clinical trial comparing MDMA, MDA, Lys-MDMA, and Lys-MDA has been completed as of August 2024.

(<i>R</i>)-MDMA Psychoactive drug taken by mouth

(R)-3,4-Methylenedioxy-N-methylamphetamine ((R)-MDMA), also known as (R)-midomafetamine or as levo-MDMA, is the (R)- or levorotatory (l-) enantiomer of 3,4-methylenedioxy-N-methylamphetamine (MDMA; midomafetamine; "ecstasy"), a racemic mixture of (R)-MDMA and (S)-MDMA. Like MDMA, (R)-MDMA is an entactogen or empathogen. It is taken by mouth.

References

  1. 1 2 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).
  2. 1 2 3 Clinical trial number NCT04847206 for "Effects of MDMA-like Substances in Healthy Subjects (MDMA-like)" at ClinicalTrials.gov
  3. 1 2 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.
  4. 1 2 "(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.
  5. 1 2 3 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.