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.[19]
The drug is almost unknown in the western world and is neither used in medicine nor 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 a scheduled substance in most countries, despite its multiple therapeutic applications and reported lack of significant
abuse potential.[20]
Mesocarb had erroneously been referred to as a
prodrug of
amphetamine[21] but 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 gas chromatography method.[22] More recent studies using mass spectroscopy show that negligible levels of amphetamine are released from mesocarb metabolism.[19]
Chemistry
Mesocarb is a
mesoionicsydnone imine. It has the amphetamine-backbone present, except that the RN has a complicated imine side-chain present.
Preparation
Feprosidnine (Sydnophen) is converted from the hydrochloride salt (1) into the freebase amine (2). This is then treated with
phenylisocyanate (3).
^Anokhina IP, Zabrodin GD, Svirinovskiĭ I (1974). "[Characteristics of the central action of sidnocarb]" [Characteristics of the central action of sidnocarb]. Zhurnal Nevropatologii I Psikhiatrii Imeni S.S. Korsakova (in Russian). 74 (4): 594–602.
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^Rudenko GM, Altshuler RA (1979). "Peculiarities of clinical activity and pharmacokinetics of sydnocarb (sydnocarbum), an original psychostimulant". Agressologie. 20 (D): 265–270.
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^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.
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^Vinar O, Klein DF, Potter WZ, Gause EM (December 1991). "A survey of psychotropic medications not available in the United States". Neuropsychopharmacology. 5 (4): 201–217.
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^Turova NF, Misionzhnik EI, 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]. Voprosy Meditsinskoi Khimii (in Russian). 34 (1): 47–50.
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^Krasov VA (1988). "[Sidnocarb treatment of young schoolchildren with the hyperdynamic syndrome]" [Sidnocarb treatment of young schoolchildren with the hyperdynamic syndrome]. Zhurnal Nevropatologii I Psikhiatrii Imeni S.S. Korsakova (in Russian). 88 (8): 97–101.
PMID3195293.
^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.
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^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]. Kosmicheskaia Biologiia I Aviakosmicheskaia Meditsina (in Russian). 22 (6): 66–73.
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^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.
PMID16579065.
^Erdö SL, Kiss B, Rosdy B (1981). "Inhibition of dopamine uptake by a new psychostimulant mesocarb (Sydnocarb)". Polish Journal of Pharmacology and Pharmacy. 33 (2): 141–147.
PMID7312716.
^
abGruner 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.
PMID21300706.
S2CID9985668.
^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". Pharmacology, Biochemistry, and Behavior. 69 (3–4): 653–658.
doi:
10.1016/S0091-3057(01)00574-3.
PMID11509228.
S2CID32739707.
^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". Annals of the New York Academy of Sciences. 914 (1): 137–145.
Bibcode:
2000NYASA.914..137A.
doi:
10.1111/j.1749-6632.2000.tb05191.x.
PMID11085316.
S2CID12326076.
^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.
PMID9527506.
^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.
PMID14698267.
^Michail D. Maschkovskij, 6 More », DE2028880 (1979 to Vsesojuznyj Nautschno-Issledovatelskij Chimiko-Farmacevtitscheskij Institut Imeni Sergo Ordschonikidze, Moskau).
^Mikhail Davidovich Mashkovsky, et al. GB1262830 (1972 to Vni Khim Farmatsevtichesky I I).