Mesocarb

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Mesocarb
Mesocarb.svg
Clinical data
Trade names Sidnocarb, Sydnocarb, Synocarb
Other namesFensidnimine; Pharmaneocarb; Sydnocarbum; N-Phenylcarbamoyl-3-(β-phenylisopropyl)sydnonimine; 3-(β-Phenylisopropyl)-N-phenylcarbamoylsydnonimine; Armesocarb; MLR-1019
Routes of
administration 		Oral
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal
Identifiers
  • 5-(Phenylcarbamoylimino)-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
CAS Number
PubChem CID
PubChemSID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C18H18N4O2
Molar mass 322.368 g·mol−1
3D model (JSmol)
  • O=C(\N=C1/C=[N+](\[N-]O1)C(C)Cc2ccccc2)Nc3ccccc3
  • InChI=1S/C18H18N4O2/c1-14(12-15-8-4-2-5-9-15)22-13-17(24-21-22)20-18(23)19-16-10-6-3-7-11-16/h2-11,13-14H,12H2,1H3,(H,19,23)/b20-17+ Yes check.svgY
  • Key:DMHQLXUFCQSQQQ-LVZFUZTISA-N Yes check.svgY
   (verify)

Mesocarb, sold under the brand name Sidnocarb or Sydnocarb and known by the developmental code name MLR-1019, is a psychostimulant medication which has been used in the treatment of psychiatric disorders and for a number of other indications in the Soviet Union and Russia. [2] [3] It is currently under development for the treatment of Parkinson's disease and sleep disorders. [4] [5] It is taken by mouth.

Contents

The drug is a selective dopamine reuptake inhibitor (DRI). [6] [7] [8] [9] It is an unusual and unique DRI, acting as a negative allosteric modulator and non-competitive inhibitor of the dopamine transporter (DAT). [6] [7] [8] Chemically, mesocarb contains amphetamine within its structure but has been modified and extended at the amine with a sydnone imine-containing moiety. [10] [2] [3]

Mesocarb was first described by 1971. [2] [11] [12] [9] In 2021, its nature as a DAT allosteric modulator was reported. [6] [7] [8] As of April 2023, mesocarb is in phase 1 clinical trials for Parkinson's disease and in the preclinical stage of development for sleep disorders. [5]

Medical uses

Mesocarb was originally developed in the Soviet Union in the 1970s [13] [14] for a variety of indications including asthenia, apathy, adynamia, and some clinical aspects of depression and schizophrenia. [15] [16] Mesocarb was used for counteracting the sedative effects of benzodiazepines, [17] increasing workload capacity and cardiovascular function, [18] treatment of attention deficit hyperactivity disorder (ADHD) in children, [19] [20] as a nootropic, [21] and as a drug to enhance resistance to extremely cold temperatures. [22] [23] It has also been reported to have antidepressant and anticonvulsant properties. [24]

Available forms

Mesocarb was sold in Russia as 5 mg oral tablets under the brand name Sydnocarb.[ citation needed ]

Pharmacology

Pharmacodynamics

Mesocarb has been found to act as a selective dopamine reuptake inhibitor (DRI) by blocking the actions of the dopamine transporter (DAT), [9] [25] and lacks the dopamine release characteristic of stimulants such as dextroamphetamine. [26] [27] [28] It was the most selective DAT inhibitor amongst an array of other DAT inhibitors to which it was compared. [25]

The inhibitory potencies (IC50 Tooltip half-maximal inhibitory concentration) of mesocarb at the human monoamine transporters in vitro have been reported to be 0.49 ± 0.14 µM at the DAT, 34.9 ± 14.08 µM at the norepinephrine transporter (NET) (71-fold lower), and 494.9 ± 17.00 µM at the serotonin transporter (1,010-fold lower). [8]

In 2021, it was discovered that mesocarb is not a conventional DRI but acts as a DAT allosteric modulator or non-competitive inhibitor and has atypical effects relative to conventional DRIs. [6] [7] [8]

Pharmacokinetics

Hydroxylated metabolites can be detected in urine for up to 10 days after consumption. [29]

Mesocarb had erroneously been referred to as a prodrug of amphetamine. [30] However, this was based on older literature that relied on gas chromatography as an analytical method. Subsequently, with the advent of mass spectroscopy, it has been shown that presence of amphetamine in prior studies was an artifact of the gas chromatography method. [31] More recent studies using mass spectroscopy show that negligible levels of amphetamine are released from mesocarb metabolism. [29]

Chemistry

Mesocarb, also known as 3-(β-phenylisopropyl)-N-phenylcarbamoylsydnonimine, is a substituted phenethylamine and amphetamine and a mesoionic sydnone imine. [10] [2] [3] It has the amphetamine backbone present, except that the RN has a complicated imine side chain present. [10] [2] [3]

It is structurally related to feprosidnine (Sydnophen; 3-(α-methylphenylethyl)sydnone imine). [24]

Synthesis

Patents: Mesocarb synthesis.svg
Patents:

Feprosidnine (Sydnophen) is converted from the hydrochloride salt (1) into the freebase amine (2). This is then treated with phenylisocyanate (3).

History

Mesocarb was first described in the scientific literature by 1971. [2] [11] [12] [9]

Society and culture

Names

Mesocarb is the generic name of the drug and its INN Tooltip International Nonproprietary Name. [10] It is also known by the synonym fensidnimine as well as by the brand names Sydnocarb and Synocarb. [2] [3] [10] [34] The drug is additionally known by its developmental code name MLR-1019 (for Parkinson's disease and other indications). [5]

Status

Mesocarb is almost unknown in the western world and is neither used in medicine nor studied scientifically to any great extent outside of Russia and other countries in the former Soviet Union. It has however been added to the list of drugs under international control and is a scheduled substance in most countries, despite its multiple therapeutic applications and reported lack of significant abuse potential. [35]

Research

Parkinson's disease

Mesocarb has been under development for the treatment of Parkinson's disease since 2016. [4] [5] As of April 2023, it is in phase 1 clinical trials for this indication. [5] A phase 2 trial is being planned. [5] It is also in the preclinal stage of development for sleep disorders. [5] It was previously approved for treatment of psychiatric disorders, but it was withdrawn from the market. [5]

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. 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">Methylphenidate</span> Central nervous system stimulant

Methylphenidate, sold under the brand names Ritalin and Concerta among others, is a central nervous system (CNS) stimulant used medically to treat attention deficit hyperactivity disorder (ADHD) and, to a lesser extent, narcolepsy. It is a primary medication for ADHD ; it may be taken by mouth or applied to the skin, and different formulations have varying durations of effect. For ADHD, the effectiveness of methylphenidate is comparable to atomoxetine but modestly lower than amphetamines, alleviating the executive functioning deficits of sustained attention, inhibition, working memory, reaction time and emotional self-regulation.

<span class="mw-page-title-main">Monoamine transporter</span> Proteins that function as integral plasma-membrane transporters

Monoamine transporters (MATs) are proteins that function as integral plasma-membrane transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are serotonin transporters (SERTs), dopamine transporters (DATs), and norepinephrine transporters (NETs) and are responsible for the reuptake of their associated amine neurotransmitters. MATs are located just outside the synaptic cleft (peri-synaptically), transporting monoamine transmitter overflow from the synaptic cleft back to the cytoplasm of the pre-synaptic neuron. MAT regulation generally occurs through protein phosphorylation and post-translational modification. Due to their significance in neuronal signaling, MATs are commonly associated with drugs used to treat mental disorders as well as recreational drugs. Compounds targeting MATs range from medications such as the wide variety of tricyclic antidepressants, selective serotonin reuptake inhibitors such as fluoxetine (Prozac) to stimulant medications such as methylphenidate (Ritalin) and amphetamine in its many forms and derivatives methamphetamine (Desoxyn) and lisdexamfetamine (Vyvanse). Furthermore, drugs such as MDMA and natural alkaloids such as cocaine exert their effects in part by their interaction with MATs, by blocking the transporters from mopping up dopamine, serotonin, and other neurotransmitters from the synapse.

A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dopamine not absorbed by the postsynaptic neuron is blocked from re-entering the presynaptic neuron. This results in increased extracellular concentrations of dopamine and increase in dopaminergic neurotransmission.

<span class="mw-page-title-main">Norepinephrine reuptake inhibitor</span> Class of drug

A norepinephrine reuptake inhibitor or noradrenaline reuptake inhibitor or adrenergic reuptake inhibitor (ARI), is a type of drug that acts as a reuptake inhibitor for the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline) by blocking the action of the norepinephrine transporter (NET). This in turn leads to increased extracellular concentrations of norepinephrine and epinephrine and therefore can increase adrenergic neurotransmission.

<span class="mw-page-title-main">Dopamine transporter</span> Mammalian protein found in Homo sapiens

The dopamine transporter is a membrane-spanning protein coded for in humans by the SLC6A3 gene, that pumps the neurotransmitter dopamine out of the synaptic cleft back into cytosol. In the cytosol, other transporters sequester the dopamine into vesicles for storage and later release. Dopamine reuptake via DAT provides the primary mechanism through which dopamine is cleared from synapses, although there may be an exception in the prefrontal cortex, where evidence points to a possibly larger role of the norepinephrine transporter.

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

Phenylpiracetam, is a phenyl-substituted analog of the drug piracetam. It was developed in 1983 as a medication for Soviet Cosmonauts to treat the prolonged stresses of working in space. Phenylpiracetam was created at the Russian Academy of Sciences Institute of Biomedical Problems in an effort led by psychopharmacologist Valentina Ivanovna Akhapkina. In Russia it is now available as a prescription drug. Research on animals has indicated that phenylpiracetam may have anti-amnesic, antidepressant, anticonvulsant, anxiolytic, and memory enhancement effects.

<span class="mw-page-title-main">Dopaminergic</span> Substance related to dopamine functions

Dopaminergic means "related to dopamine", a common neurotransmitter. Dopaminergic substances or actions increase dopamine-related activity in the brain.

<span class="mw-page-title-main">Phenyltropane</span> Class of chemical compounds

Phenyltropanes (PTs) were originally developed to reduce cocaine addiction and dependency. In general these compounds act as inhibitors of the plasmalemmal monoamine reuptake transporters. This research has spanned beyond the last couple decades, and has picked up its pace in recent times, creating numerous phenyltropanes as research into cocaine analogues garners interest to treat addiction.

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

Feprosidnine (Sydnophen) is a stimulant drug which was developed in the USSR in the 1970s. It is structurally related to another Russian drug mesocarb but unlike mesocarb, was withdrawn earlier from production. In comparison with mesocarb it has own antidepressant activity, which makes it useful in treating depressions. Indications of feprosidnine included apathic, asthenic depressions, fatigue, apathic syndrome, narcolepsy and other similar conditions. Therapeutic range of doses: 10-50mg a day. Sydnophen has multiple mechanisms of action, the relative importance of which has not been clearly established. Effects on the body include reversible monoamine oxidase inhibition, cholinergic, adrenergic, opioid and nitric oxide donating actions, all of which may contribute to its pharmacological effects to some extent.

<span class="mw-page-title-main">Bromantane</span> Stimulant drug

Bromantane, sold under the brand name Ladasten, is an atypical central nervous system (CNS) stimulant and anxiolytic drug of the adamantane family that is related to amantadine and memantine. Medically, it is approved in Russia for the treatment of neurasthenia. Although the effects of bromantane have been determined to be dependent on the dopaminergic and possibly serotonergic neurotransmitter systems, its exact mechanism of action is unknown, and is distinct in its properties relative to typical stimulants such as amphetamine. Bromantane has sometimes been described as an actoprotector.

<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of a monoamine neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitter. Many drugs induce their effects in the body and/or brain via the release of monoamine neurotransmitters, e.g., trace amines, many substituted amphetamines, and related compounds.

A dopamine releasing agent (DRA) is a type of drug which induces the release of dopamine in the body and/or brain. No selective and robust DRAs are currently known. On the other hand, many releasing agents of both dopamine and norepinephrine and of serotonin, norepinephrine, and dopamine are known. Serotonin–dopamine releasing agents (SDRAs), for instance 5-chloro-αMT, are much more rare and are not selective for dopamine release but have also been developed. Examples of major NDRAs include the psychostimulants amphetamine and methamphetamine, while an example of an SNDRA is the entactogen methylenedioxymethamphetamine (MDMA). These drugs are frequently used for recreational purposes and encountered as drugs of abuse. Selective DRAs, as well as NDRAs, have medical applications in the treatment of attention deficit hyperactivity disorder (ADHD).

<span class="mw-page-title-main">RTI-113</span> Chemical compound

RTI(-4229)-113 is a stimulant drug which acts as a potent and fully selective dopamine reuptake inhibitor (DRI). It has been suggested as a possible substitute drug for the treatment of cocaine addiction. "RTI-113 has properties that make it an ideal medication for cocaine abusers, such as an equivalent efficacy, a higher potency, and a longer duration of action as compared to cocaine." Replacing the methyl ester in RTI-31 with a phenyl ester makes the resultant RTI-113 fully DAT specific. RTI-113 is a particularly relevant phenyltropane cocaine analog that has been tested on squirrel monkeys. RTI-113 has also been tested against cocaine in self-administration studies for DAT occupancy by PET on awake rhesus monkeys. The efficacy of cocaine analogs to elicit self-administration is closely related to the rate at which they are administered. Slower onset of action analogs are less likely to function as positive reinforcers than analogues that have a faster rate of onset.

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

Echinopsidine (Adepren) is an antidepressant that was under development in Bulgaria for the treatment of depression. It increases serotonin, norepinephrine, and dopamine levels in the brain and is believed to act as a monoamine oxidase inhibitor (MAOI). Echinopsidine is found naturally in Echinops echinatus along with the related alkaloids echinopsine and echinozolinone.

<span class="mw-page-title-main">Amphetamine dependence</span> Medical condition

Amphetamine dependence refers to a state of psychological dependence on a drug in the amphetamine class. Stimulants such as amphetamines and cocaine do not cause somatic symptoms upon cessation of use but rather neurological-based mental symptoms.

<span class="mw-page-title-main">SoRI-20041</span> Chemical compound

SoRI-20041 is an "antagonist-like" allosteric modulator of amphetamine-induced dopamine release. SoRI-20041 is believed to be the first example of a drug that separately modulates uptake versus release in the dopamine transporter ; it produces the same effects as SoRI-20040 and SoRI-9804 in uptake assays and binding assays, inhibiting the re-uptake of dopamine, but does not modulate d-amphetamine-induced DA release by inhibiting that as well, like 'agonists' of the series do.

A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamine transporters (MATs), which include the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT). This in turn results in an increase in the synaptic concentrations of one or more of these neurotransmitters and therefore an increase in monoaminergic neurotransmission.

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">JJC8-088</span> Cocaine-like dopamine reuptake inhibitor derived from modafinil

JJC8-088 is a dopamine reuptake inhibitor (DRI) that was derived from the wakefulness-promoting agent modafinil.

References

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  13. ↑ GB Patent 1262830 - NOVEL SYDNONIMINE DERIVATIVE
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  15. ↑ Rudenko GM, Altshuler RA (1979). "Peculiarities of clinical activity and pharmacokinetics of sydnocarb (sydnocarbum), an original psychostimulant". Agressologie. 20 (D): 265–270. PMID   45391.
  16. ↑ Witkin JM, Savtchenko N, Mashkovsky M, Beekman M, Munzar P, Gasior M, et al. (March 1999). "Behavioral, toxic, and neurochemical effects of sydnocarb, a novel psychomotor stimulant: comparisons with methamphetamine". The Journal of Pharmacology and Experimental Therapeutics. 288 (3): 1298–1310. PMID   10027871.
  17. ↑ Valueva LN, Tozhanova NM (1982). "[Sidnocarb correction of the adverse effects of benzodiazepine tranquilizers]" [Sidnocarb correction of the adverse effects of benzodiazepine tranquilizers]. Zhurnal Nevropatologii I Psikhiatrii imeni S.S. Korsakova (in Russian). 82 (8): 92–97. PMID   6127851.
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  21. ↑ Ganiev MM, Kharlamov AN, Raevskiĭ KS, Guseĭnov DI (October 1987). "[Effect of sidnocarb on learning and memory]" [Effect of sidnocarb on learning and memory]. Biulleten' Eksperimental'noi Biologii I Meditsiny (in Russian). 104 (10): 453–454. PMID   3676468.
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  23. ↑ Levina MN, Badyshtov BA, Gan'shina TS (2006). "[Thermoprotector properties of a combination of sydnocarb with ladasten]" [Thermoprotector properties of a combination of sydnocarb with ladasten]. Eksperimental'naia i Klinicheskaia Farmakologiia (in Russian). 69 (1): 71–73. PMID   16579065.
  24. 1 2 Kawase M, Sakagami H, Motohashi N (2007). "The Chemistry of Bioactive Mesoionic Heterocycles". Bioactive Heterocycles VII. Vol. 16. Berlin, Heidelberg: Springer Berlin Heidelberg. p. 135–152. doi:10.1007/7081_2007_096. ISBN   978-3-642-00335-6. Mesocarb (sydnocarb) (13) and Feprosidnine (sydnofen) (14) are stimulants developed in Russia in the 1970s. Mesocarb is sold as a drug in Russia. However, it is almost unknown in Western countries and is not used in medicine. It has been shown to act as a dopamine reuptake inhibitor, antidepressant, and anticonvulsant [7, 8].
  25. 1 2 Gruner JA, Mathiasen JR, Flood DG, Gasior M (May 2011). "Characterization of pharmacological and wake-promoting properties of the dopaminergic stimulant sydnocarb in rats". The Journal of Pharmacology and Experimental Therapeutics. 337 (2): 380–390. doi:10.1124/jpet.111.178947. PMID   21300706. S2CID   9985668.
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  28. ↑ Gainetdinov RR, Sotnikova TD, Grekhova TV, Rayevsky KS (December 1997). "Effects of a psychostimulant drug sydnocarb on rat brain dopaminergic transmission in vivo". European Journal of Pharmacology. 340 (1): 53–58. doi:10.1016/S0014-2999(97)01407-6. PMID   9527506.
  29. 1 2 Shpak AV, Appolonova SA, Semenov VA (January 2005). "Validation of liquid chromatography-electrospray ionization ion trap mass spectrometry method for the determination of mesocarb in human plasma and urine". Journal of Chromatographic Science. 43 (1): 11–21. doi: 10.1093/chromsci/43.1.11 . PMID   15808002.
  30. ↑ Dettmeyer R, Verhoff MA, Schütz HF (9 October 2013). Forensic Medicine: Fundamentals and Perspectives. Springer Science & Business Media. pp. 519–. ISBN   978-3-642-38818-7.
  31. ↑ Appolonova SA, Shpak AV, Semenov VA (February 2004). "Liquid chromatography-electrospray ionization ion trap mass spectrometry for analysis of mesocarb and its metabolites in human urine". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 800 (1–2): 281–289. doi:10.1016/j.jchromb.2003.10.071. PMID   14698267.
  32. ↑ Michail D. Maschkovskij, 6 More », DE2028880 (1979 to Vsesojuznyj Nautschno-Issledovatelskij Chimiko-Farmacevtitscheskij Institut Imeni Sergo Ordschonikidze, Moskau).
  33. ↑ Mikhail Davidovich Mashkovsky, et al. GB1262830 (1972 to Vni Khim Farmatsevtichesky I I).
  34. ↑ "CAS Common Chemistry". CAS Common Chemistry. 16 September 2024. Retrieved 16 September 2024.
  35. ↑ Rudenko GM, Altshuler RA (1978). "[Experimental and clinical study of Sydnocarb]". Hung Pharmacotherapy (in Russian). 124: 150–154.


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