Mesocarb

Mesocarb

Mesocarb
Systematic (IUPAC) name
5-(Phenylcarbamoylimino)-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
Clinical data
Legal status
  • Class C (UK), Schedule III (Can)
Routes Oral
Pharmacokinetic data
Metabolism hepatic
Excretion renal
Identifiers
CAS number  YesY
ATC code None
PubChem
ChemSpider  YesY
UNII  YesY
Chemical data
Formula C18H18N4O2 
Mol. mass 322.36 g/mol
 YesY   

Mesocarb (Sidnocarb, Sydnocarb) is a stimulant drug which was developed in the USSR in the 1970s.[1][2] It has been shown to act as a dopamine reuptake inhibitor[3][4] which is slower acting but longer lasting than dextroamphetamine.[5]

Mesocarb was used for a variety of applications;[6] these include counteracting the sedative effects of benzodiazepine drugs,[7] increasing workload capacity and cardiovascular function,[8] treatment of ADHD and hyperactivity in children,[9][10] as a nootropic,[11] and as a drug to enhance resistance to extremely cold temperatures.[12][13] It is also listed as having antidepressant and anticonvulsant properties.

Mesocarb was 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.[14]

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.[15]

Chemistry

Mesocarb is a mesoionic sydnone imine. It has the amphetamine-backbone present, except that the RN has a complicated imine side-chain present.

References

  1. ^ GB Patent 1262830 - NOVEL SYDNONIMINE DERIVATIVE
  2. ^ Anokhina IP, Zabrodin GD, Svirinovskiĭ IaE (1974). "[Characteristics of the central action of sidnocarb]" [Characteristics of the central action of sidnocarb]. Zh Nevropatol Psikhiatr Im S S Korsakova (in Russian) 74 (4): 594–602.  
  3. ^ Anderzhanova EA, Afanas'ev II, Kudrin VS, Rayevsky KS (September 2000). "Effect of d-amphetamine and sydnocarb on the extracellular level of dopamine, 3,4-dihydroxyphenylacetic acid, and hydroxyl radicals generation in rat striatum". Ann N Y Acad Sci. 914: 137–45.  
  4. ^ Gainetdinov RR, Sotnikova TD, Grekhova TV, Rayevsky KS (December 1997). "Effects of a psychostimulant drug sydnocarb on rat brain dopaminergic transmission in vivo". Eur J Pharmacol. 340 (1): 53–8.  
  5. ^ Afanas'ev II, Anderzhanova EA, Kudrin VS, Rayevsky KS (2001). "Effects of amphetamine and sydnocarb on dopamine release and free radical generation in rat striatum". Pharmacol Biochem Behav. 69 (3–4): 653–8.  
  6. ^ Witkin JM, Savtchenko N, Mashkovsky M, et al. (1 March 1999). "Behavioral, toxic, and neurochemical effects of sydnocarb, a novel psychomotor stimulant: comparisons with methamphetamine". J Pharmacol Exp Ther. 288 (3): 1298–310.  
  7. ^ Valueva LN, Tozhanova NM (1982). "[Sidnocarb correction of the adverse effects of benzodiazepine tranquilizers]" [Sidnocarb correction of the adverse effects of benzodiazepine tranquilizers]. Zh Nevropatol Psikhiatr Im S S Korsakova (in Russian) 82 (8): 92–7.  
  8. ^ Vinar O, Klein DF, Potter WZ, Gause EM (December 1991). "A survey of psychotropic medications not available in the United States". Neuropsychopharmacology 5 (4): 201–17.  
  9. ^ Turova NF, Misionzhnik EIu, Ermolina LA, Aziavchik AV, Krasov VA (1988). "[Excretion of monoamines, their precursors and metabolites in the hyperactivity syndrome in mentally defective children]" [Excretion of monoamines, their precursors and metabolites in the hyperactivity syndrome in mentally defective children]. Vopr Med Khim. (in Russian) 34 (1): 47–50.  
  10. ^ Krasov VA (1988). "[Sidnocarb treatment of young schoolchildren with the hyperdynamic syndrome]" [Sidnocarb treatment of young schoolchildren with the hyperdynamic syndrome]. Zh Nevropatol Psikhiatr Im S S Korsakova (in Russian) 88 (8): 97–101.  
  11. ^ Ganiev MM, Kharlamov AN, Raevskiĭ KS, Guseĭnov DIa (October 1987). "[Effect of sidnocarb on learning and memory]" [Effect of sidnocarb on learning and memory]. Biull Eksp Biol Med (in Russian) 104 (10): 453–4.  
  12. ^ Barer AS, Lakota NG, Ostrovskaia GZ, Shashkov VS (Nov–Dec 1988). "[Pharmacologic correction of the effect of cold on man]" [Pharmacologic correction of the effect of cold on man]. Kosm Biol Aviakosm Med (in Russian) 22 (6): 66–73.  
  13. ^ 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]. Eksp Klin Farmakol (in Russian) 69 (1): 71–3.  
  14. ^ 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". J Chromatogr Sci 43 (1): 11–21.  
  15. ^ Rudenko GM, Altshuler RA (1978). "[Experimental and clinical study of Sydnocarb]". Hung Pharmacotherapy (in Russian) 124: 150–4.