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Mesocarb



Mesocarb
Systematic (IUPAC) name
5-(Phenylcarbamoylimino)-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
Identifiers
CAS number 34262-84-5
ATC code  ?
PubChem 71932
Chemical data
Formula C18H18N4O2 
Mol. mass 322.36 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism hepatic
Half life  ?
Excretion renal
Therapeutic considerations
Pregnancy cat.

?

Legal status

Class C (UK), Schedule III (USA)

Routes Oral

Mesocarb (Sidnocarb, Sydnocarb) is a stimulant drug which was developed in the USSR in the 1970s. [1] It has been shown to act as a dopamine reuptake inhibitor[2][3] which is slower acting but longer lasting and less neurotoxic than dextroamphetamine.[4]

Additional recommended knowledge

Mesocarb is still used for a variety of applications,[5] including counteracting the sedative effects of benzodiazepine drugs,[6] increasing workload capacity and cardiovascular function,[7] treatment of ADHD and hyperactivity in children,[8][9] as a nootropic,[10] and as a drug to enhance resistance to extremely cold temperatures.[11][12] It is also listed as having antidepressant and anticonvulsant properties.

Mesocarb is sold in Russia as 5 milligram tablets under the brand name Sydnocarb. Hydroxylated metabolites can be detected in urine for up to 10 days after consumption, reflecting a relatively long half-life.[13]

Mesocarb is almost unknown in the western world and is neither used in medicine or studied scientifically to any great extent outside Russia and other countries in the former Soviet Union. It has however been added to the list of drugs under international control and is illegal in most countries, despite its multiple therapeutic applications and the lack of significant abuse potential seen in clinical practice.[14]

Chemistry

Mesocarb is a mesoionic sydnone imine.

References

  1. ^ Anokhina IP, Zabrodin GD, Svirinovskii IaE. Characteristics of the central action of sidnocarb. Zhurnal Nevropatologii i Psikhiatrii Imeni S S Korsakova. 1974;74(4):594-602. (Russian)
  2. ^ Anderzhanova EA, Afanas'ev II, Kudrin VS, Rayevsky KS. Effect of d-amphetamine and sydnocarb on the extracellular level of dopamine, 3,4-dihydroxyphenylacetic acid, and hydroxyl radicals generation in rat striatum. Annals of the New York Academy of Sciences. 2000 Sep;914:137-45.
  3. ^ Gainetdinov RR, Sotnikova TD, Grekhova TV and Rayevsky KS (1997) Effect of a psychostimulant drug Sydnocarb on rat brain dopaminergic transmission in vivo. European Journal of Pharmacology 340:53–58.
  4. ^ Afanas'ev II, Anderzhanova EA, Kudrin VS, Rayevsky KS. Effects of amphetamine and sydnocarb on dopamine release and free radical generation in rat striatum. Pharmacology Biochemistry and Behavior. 2001 Jul-Aug;69(3-4):653-8.
  5. ^ Witkin JM, Savtchenko N, Mashkovsky M, Beekman M, Munzar P, Gasior M, Goldberg SR, Ungard JT, Kim J, Shippenberg T, Chefer V. Behavioral, toxic, and neurochemical effects of sydnocarb, a novel psychomotor stimulant: comparisons with methamphetamine. Journal of Pharmacology and Experimental Therapeutics. 1999 Mar;288(3):1298-310.
  6. ^ Valueva LA and Tozhanova NM (1982) Correction by Sydnocarb of side effects produced by tranquilizers of benzodiazepine series. Journal of Neurology, Neurosurgery and Psychiatry 1982; 9:92–97.
  7. ^ Vinar O, Klein DF, Potter WZ, Gause EM. A survey of psychotropic medications not available in the United States. Neuropsychopharmacology 1991; 5:201
  8. ^ Turova NF, Misionzhnik EIu, Ermolina LA, Aziavchik AV, Krasov VA. Excretion of monoamines, their precursors and metabolites in the hyperactivity syndrome in mentally defective children. Voprosy Meditsinskoi Khimii. 1988 Jan-Feb;34(1):47-50. (Russian)
  9. ^ Krasov VA. Sidnocarb treatment of young schoolchildren with the hyperdynamic syndrome. Zhurnal Nevropatologii i Psikhiatrii Imeni S S Korsakova. 1988;88(8):97-101. (Russian)
  10. ^ Ganiev MM, Kharlamov AN, Raevskii KS, Guseinov DIa. Effect of sidnocarb on learning and memory. Biulleten Eksperimental Biologii i Meditsiny. 1987 Oct;104(10):453-4. (Russian)
  11. ^ Barer AS, Lakota NG, Ostrovskaia GZ, Shashkov VS. Pharmacologic correction of the effect of cold on man. Kosmicheskaia Biologiia i Aviakosmicheskaia Meditsina. 1988 Nov-Dec;22(6):66-73. (Russian)
  12. ^ Levina MN, Badyshtov BA, Gan'shina TS. Thermoprotector properties of a combination of sydnocarb with ladasten. Eksperimental'naia i Klinicheskaia Farmakologiia. 2006 Jan-Feb;69(1):71-3. (Russian)
  13. ^ Shpak AV, Appolonova SA, Semenov VA. 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. 2005 Jan;43(1):11-21.
  14. ^ Rudenko GM and Altshuler RA (1978) Experimental and clinical study of Sydnocarb. Hung Pharmacotherapy, 124:150–154 (Russian)
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Mesocarb". A list of authors is available in Wikipedia.
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