Mesocarb: Difference between revisions

{{drugbox

| verifiedrevid = 443501502

|

|IUPAC_name = 5-(Phenylcarbamoylimino)-3-(1-phenylpropan-2-yl)-5''H''-1,2,3-oxadiazol-3-ium-2-ide

| image= Sidnocarb.svg

| width= 260

| InChI = 1/C18H18N4O2/c1-14(12-15-8-4-2-5-9-15)22-13-17(24-21-22)20-18(23)19-16-10-6-3-7-11-16/h2-11,13-14H,12H2,1H3,(H,19,23)/b20-17+

| InChIKey = DMHQLXUFCQSQQQ-LVZFUZTIBV

| CAS_number= 34262-84-5

| ATC_prefix= none

| ATC_suffix=

| PubChem= 71932

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID=16736988

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank=

| C=18 | H=18 | N=4 | O=2

| molecular_weight = 322.36 g/mol

| bioavailability=

| metabolism = hepatic

| elimination_half-life=

| excretion = renal

| pregnancy_category =

| legal_status = Class C (UK), Schedule III (Can)

| routes_of_administration= Oral

'''Mesocarb''' ('''Sidnocarb''', '''Sydnocarb''') is a [[stimulant]] drug which was developed in the [[USSR]] in the 1970s.<ref>{{cite journal |author=Anokhina IP, Zabrodin GD, Svirinovskiĭ IaE |title=[Characteristics of the central action of sidnocarb] |language=Russian |journal=Zh Nevropatol Psikhiatr Im S S Korsakova |volume=74 |issue=4 |pages=594–602 |year=1974 |pmid=4825943 |trans_title=Characteristics of the central action of sidnocarb }}</ref> It has been shown to act as a [[dopamine reuptake inhibitor]]<ref>{{cite journal |doi=10.1111/j.1749-6632.2000.tb05191.x |author=Anderzhanova EA, Afanas'ev II, Kudrin VS, Rayevsky KS |title=Effect of d-amphetamine and sydnocarb on the extracellular level of dopamine, 3,4-dihydroxyphenylacetic acid, and hydroxyl radicals generation in rat striatum |journal=Ann N Y Acad Sci. |volume=914 |pages=137–45 |year=2000 |month= September|pmid=11085316 |url=http://www.blackwell-synergy.com/openurl?genre=article&sid=nlm:pubmed&issn=0077-8923&date=2000&volume=914&spage=137}}</ref><ref>{{cite journal |author=Gainetdinov RR, Sotnikova TD, Grekhova TV, Rayevsky KS |title=Effects of a psychostimulant drug sydnocarb on rat brain dopaminergic transmission in vivo |journal=Eur J Pharmacol. |volume=340 |issue=1 |pages=53–8 |year=1997 |month= December|pmid=9527506 |url=http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(97)01407-6 |doi=10.1016/S0014-2999(97)01407-6}}</ref> which is slower acting but longer lasting and less neurotoxic than [[dextroamphetamine]].<ref>{{cite journal |author=Afanas'ev II, Anderzhanova EA, Kudrin VS, Rayevsky KS |title=Effects of amphetamine and sydnocarb on dopamine release and free radical generation in rat striatum |journal=Pharmacol Biochem Behav. |volume=69 |issue=3-4 |pages=653–8 |year=2001 |pmid=11509228 |url=http://linkinghub.elsevier.com/retrieve/pii/S0091-3057(01)00574-3 |doi=10.1016/S0091-3057(01)00574-3}}</ref>

Mesocarb is still used for a variety of applications;<ref>{{cite journal |author=Witkin JM, Savtchenko N, Mashkovsky M, ''et al.'' |title=Behavioral, toxic, and neurochemical effects of sydnocarb, a novel psychomotor stimulant: comparisons with methamphetamine |journal=J Pharmacol Exp Ther. |volume=288 |issue=3 |pages=1298–310 |date=1 March 1999|pmid=10027871 |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10027871 }}</ref> these include counteracting the sedative effects of [[benzodiazepine]] drugs,<ref>{{cite journal |author=Valueva LN, Tozhanova NM |title=[Sidnocarb correction of the adverse effects of benzodiazepine tranquilizers] |language=Russian |journal=Zh Nevropatol Psikhiatr Im S S Korsakova |volume=82 |issue=8 |pages=92–7 |year=1982 |pmid=6127851 |trans_title=Sidnocarb correction of the adverse effects of benzodiazepine tranquilizers }}</ref> increasing workload capacity and cardiovascular function,<ref>{{cite journal |author=Vinar O, Klein DF, Potter WZ, Gause EM |title=A survey of psychotropic medications not available in the United States |journal=Neuropsychopharmacology |volume=5 |issue=4 |pages=201–17 |year=1991 |month= December|pmid=1804161 }}</ref> treatment of [[ADHD]] and hyperactivity in children,<ref>{{cite journal |author=Turova NF, Misionzhnik EIu, Ermolina LA, Aziavchik AV, Krasov VA |title=[Excretion of monoamines, their precursors and metabolites in the hyperactivity syndrome in mentally defective children] |language=Russian |journal=Vopr Med Khim. |volume=34 |issue=1 |pages=47–50 |year=1988 |pmid=3369126 |trans_title=Excretion of monoamines, their precursors and metabolites in the hyperactivity syndrome in mentally defective children }}</ref><ref>{{cite journal |author=Krasov VA |title=[Sidnocarb treatment of young schoolchildren with the hyperdynamic syndrome] |language=Russian |journal=Zh Nevropatol Psikhiatr Im S S Korsakova |volume=88 |issue=8 |pages=97–101 |year=1988 |pmid=3195293 |trans_title=Sidnocarb treatment of young schoolchildren with the hyperdynamic syndrome }}</ref> as a [[nootropic]],<ref>{{cite journal |author=Ganiev MM, Kharlamov AN, Raevskiĭ KS, Guseĭnov DIa |title=[Effect of sidnocarb on learning and memory] |language=Russian |journal=Biull Eksp Biol Med |volume=104 |issue=10 |pages=453–4 |year=1987 |month= October|pmid=3676468 |trans_title=Effect of sidnocarb on learning and memory }}</ref> and as a drug to enhance resistance to extremely cold temperatures.<ref>{{cite journal |author=Barer AS, Lakota NG, Ostrovskaia GZ, Shashkov VS |title=[Pharmacologic correction of the effect of cold on man] |language=Russian |journal=Kosm Biol Aviakosm Med |volume=22 |issue=6 |pages=66–73 |month=Nov-Dec |year=1988 |pmid=2906380 |trans_title=Pharmacologic correction of the effect of cold on man }}</ref><ref>{{cite journal |author=Levina MN, Badyshtov BA, Gan'shina TS |title=[Thermoprotector properties of a combination of sydnocarb with ladasten] |language=Russian |journal=Eksp Klin Farmakol |volume=69 |issue=1 |pages=71–3 |year=2006 |pmid=16579065 |trans_title=Thermoprotector properties of a combination of sydnocarb with ladasten }}</ref> 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.<ref>{{cite journal |author=Shpak AV, Appolonova SA, Semenov VA |title=Validation of liquid chromatography-electrospray ionization ion trap mass spectrometry method for the determination of mesocarb in human plasma and urine |journal=J Chromatogr Sci |volume=43 |issue=1 |pages=11–21 |year=2005 |month= January|pmid=15808002 |url=http://openurl.ingenta.com/content/nlm?genre=article&issn=0021-9665&volume=43&issue=1&spage=11&aulast=Shpak}}</ref>

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.<ref>{{cite journal |author=Rudenko GM, Altshuler RA |title=[Experimental and clinical study of Sydnocarb] |language=Russian |journal=Hung Pharmacotherapy |volume=124 |issue= |pages=150–4 |year=1978}}</ref>

== Chemistry ==

{{Reflist}}

{{Dopaminergics}}

{{Antihyperkinetics}}

[[Category:Stimulants]]

[[Category:Ureas]]

{{nervous-system-drug-stub}}

[[de:Mesocarb]]

[[ru:Мезокарб]]