Mesocarb

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Mesocarb
Sidnocarb.svg
Systematic (IUPAC) name
5-(Phenylcarbamoylimino)-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
Clinical data
Routes of
administration
Oral
Legal status
Legal status
Pharmacokinetic data
Metabolism hepatic
Excretion renal
Identifiers
CAS Number 34262-84-5 YesY
ATC code none
PubChem CID 71932
ChemSpider 16736988 YesY
UNII UMT8MP2NDU YesY
Chemical data
Formula C18H18N4O2
Molar mass 322.36 g/mol
  (verify)

Mesocarb (brand names Sidnocarb, Sydnocarb) is a stimulant drug which was developed in the USSR in the 1970s.[1][2] It has been found to act as a selective dopamine reuptake inhibitor,[3][4][5] and is less potent and slower acting but longer lasting than dextroamphetamine.[6]

Mesocarb was used for a variety of applications;[7] these include counteracting the sedative effects of benzodiazepine drugs,[8] increasing workload capacity and cardiovascular function,[9] treatment of ADHD and hyperactivity in children,[10][11] as a nootropic,[12] and as a drug to enhance resistance to extremely cold temperatures.[13][14] 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.[15]

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 reported lack of significant abuse potential.[16]

Mesocarb has been referred to as a prodrug of amphetamine.[17] Indeed, it produces amphetamine as a metabolite,[18] and amphetamine concentrations are far higher than mesocarb concentrations in human urine 22 hours post-administration (0.7–186 ng/mL and 0.004–0.17 ng/mL, respectively).[15] However, mesocarb also possesses molecular actions of its own, inhibiting the reuptake of dopamine and to a far lesser extent of norepinephrine, but not of serotonin.[3]

Chemistry[edit]

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

Preparation[edit]

Mesocarb from feprosidnine.

References[edit]

  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. PMID 4825943. 
  3. ^ a b Erdö SL, Kiss B, Rosdy B (1981). "Inhibition of dopamine uptake by a new psychostimulant mesocarb (Sydnocarb)". Pol J Pharmacol Pharm. 33 (2): 141–7. PMID 7312716. 
  4. ^ 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. doi:10.1111/j.1749-6632.2000.tb05191.x. PMID 11085316. 
  5. ^ 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. doi:10.1016/S0014-2999(97)01407-6. PMID 9527506. 
  6. ^ 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. doi:10.1016/S0091-3057(01)00574-3. PMID 11509228. 
  7. ^ 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. PMID 10027871. 
  8. ^ 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. PMID 6127851. 
  9. ^ 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. PMID 1804161. 
  10. ^ 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. PMID 3369126. 
  11. ^ 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. PMID 3195293. 
  12. ^ 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. PMID 3676468. 
  13. ^ 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. PMID 2906380. 
  14. ^ 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. PMID 16579065. 
  15. ^ a b Shpak AV, Appolonova SA, Semenov VA (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. doi:10.1093/chromsci/43.1.11. PMID 15808002. 
  16. ^ Rudenko GM, Altshuler RA (1978). "[Experimental and clinical study of Sydnocarb]". Hung Pharmacotherapy (in Russian). 124: 150–4. 
  17. ^ Reinhard Dettmeyer; Marcel A. Verhoff; Harald F. Schütz (9 October 2013). Forensic Medicine: Fundamentals and Perspectives. Springer Science & Business Media. pp. 519–. ISBN 978-3-642-38818-7. 
  18. ^ Polgár, M.; Vereczkey, L.; Szporny, L.; Czira, G.; Tamás, J.; Gács-Baitz, E.; Holly, S. (1979). "Metabolism of mesocarb in the rat". Xenobiotica. 9 (8): 511–519. doi:10.3109/00498257909087265. ISSN 0049-8254.