Mesocarb
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Mesocarb
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| Systematic (IUPAC) name | |
| 5-(Phenylcarbamoylimino)-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| 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]
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]
[edit] Chemistry
Mesocarb is a mesoionic sydnone imine. It has the amphetamine-backbone present, except that the RN has a complicated imine side-chain present.
[edit] References
- ^ 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) PMID 4825943
- ^ 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. PMID 11085316
- ^ Gainetdinov RR, Sotnikova TD, Grekhova TV and Rayevsky KS. Effects of a psychostimulant drug Sydnocarb on rat brain dopaminergic transmission in vivo. European Journal of Pharmacology 1997 Dec 4;340(1):53-8. PMID 9527506
- ^ 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. PMID 11509228
- ^ 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. PMID 10027871
- ^ Valueva LA and Tozhanova NM. Correction by Sydnocarb of side effects produced by tranquilizers of benzodiazepine series. Journal of Neurology, Neurosurgery and Psychiatry 1982; 9:92–97.
- ^ Vinar O, Klein DF, Potter WZ, Gause EM. A survey of psychotropic medications not available in the United States. Neuropsychopharmacology 1991;5:201
- ^ 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) PMID 3369126
- ^ 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) PMID 3195293
- ^ 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) PMID 3676468
- ^ 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) PMID 2906380
- ^ 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) PMID 16579065
- ^ 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. PMID 15808002
- ^ Rudenko GM and Altshuler RA. Experimental and clinical study of Sydnocarb. Hung Pharmacotherapy, 1978;124:150–154 (Russian)
