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Methylphenidate
Methylphenidate
Synonyms Metylfenidat
Brand names Concerta, Ritalin (oral), Daytrana (patch)
IUPAC name

IUPAC name
methyl phenyl(2-piperidinyl)acetate
ChemSpider

4015

DrugBank

DB00422

PubChem

4158

PDB fields

N/A

Formula

C14H19NO2

InChI
InChI
1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3
InChIKey
InChIKey
DUGOZIWVEXMGBE-UHFFFAOYSA-N
SMILES
SMILES
COC(=O)C(C1CCCCN1)C2=CC=CC=C2
(Jmol 3D structure)
Mol. mass

233.3062 g/mol

Ritalin

Ritalin box

Methylphenidate is a noradrenaline-dopamine reuptake inhibitor (NDRI) that is primarily used to treat ADHD and narcolepsy. Its NDRI action is said to be competitive, as it binds to the noradrenaline and dopamine transporters, instead of activating TAAR1 like the amfetamines do.[1][2] Methylphenidate is generally considered a milder stimulant than the amfetamines and in animal models it does not appear to be associated with the neuronal cell death typical of the amfetamines. Despite this it produces significant immediate improvements in cognition, including in healthy individuals.[3][4] It has also been used to treat Parkinson's disease and the associated fatigue, depression and other problems.[5]

A quarter of all stimulant use by university students in the U.S.A. back in 2006 used methylphenidate.[6]

PropertiesEdit

Methylphenidate hydrochloride (which is in most commercial preparations) is a white/almost white odourless crystalline powder that is freely soluble in water.[7] Methylphenidate is also a compound with two enantiomers: dexmethylphenidate and levmethylphenidate.[7] The d-form (more active) has a half-life of 6 hours whereas the l-form has a half-life of 4 hours.[7] Methylphenidate has an oral bioavailability of 11-52% (there is significant differences between the bioavailability of the drug for different individuals).[7] Methylphenidate usually takes 2 hours to start producing its effects when taken orally.[7]

StructuresEdit

Structures of methylphenidate
Methylphenidate-racemate
Dexmethylphenidate-crystal
Levomethylphenidate-crystal
350px dexmethylphenidate
350px levomethylphenidate



See alsoEdit

External linksEdit

Reference listEdit

  1. Zucchi, R; Chiellini, G; Scanlan, TS; Grandy, DK (December 2006). "Trace amine-associated receptors and their ligands.". British Journal of Pharmacology 149 (8): 967–78. doi:10.1038/sj.bjp.0706948. PMC 2014643. PMID 17088868.
  2. Sotnikova, TD; Caron, MG; Gainetdinov, RR; Grandy, DK (August 2009). "Trace amine-associated receptors as emerging therapeutic targets.". Molecular pharmacology 76 (2): 229–35. doi:10.1124/mol.109.055970. PMC 2713119. PMID 19389919.
  3. Ares-Santos, S; Granado, N; Moratalla, R (May 2013). "The role of dopamine receptors in the neurotoxicity of methamphetamine.". Journal of Internal Medicine 273 (5): 437–53. doi:10.1111/joim.12049. PMID 23600399.
  4. Mackey, S; Paulus, M (March 2013). "Are there volumetric brain differences associated with the use of cocaine and amphetamine-type stimulants?". Neuroscience and Biobehavioral Reviews 37 (3): 300–16. doi:10.1016/j.neubiorev.2012.12.003. PMC 3604030. PMID 23253945.
  5. Auriel, E; Hausdorff, JM; Giladi, N (March-April 2009). "Methylphenidate for the treatment of Parkinson disease and other neurological disorders.". Clinical Neuropharmacology 32 (2): 75–81. doi:10.1097/WNF.0B013E318170576C. PMID 18978488.
  6. Teter, CJ; McCabe, SE; LaGrange, K; Cranford, JA; Boyd, CJ (October 2006). "Illicit use of specific prescription stimulants among college students: prevalence, motives, and routes of administration.". Pharmacotherapy 26 (10): 1501–10. PMC 1794223. PMID 16999660. doi:10.1592/phco.26.10.1501. 
  7. 7.0 7.1 7.2 7.3 7.4 Brayfield, A, ed. (13 December 2013). "Methylphenidate". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 5 June 2014.

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