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| {{unreferenced|date=August 2006}}
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| {{drugbox
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| | IUPAC_name = N-methyl-N-(1-methyl-2-phenyl-ethyl)-prop-2-yn-1-amine
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| | image = Selegiline-2D-skeletal-alternative-view.png
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| | image2 = Selegiline-3D-balls.png
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| | CAS_number = 14611-51-9
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| | CAS_supplemental = [14611-52-0] <small>(HCl)</small>, [2079-54-1] <small>(deprenyl.HCl)</small>, [4530-70-5] <small>((+-)-isomer)</small>, [1205-70-5] <small>((+-)-isomer, HCl)</small>, [2323-36-6] <small>(cpd w/o isomeric designation; deprenyl)</small>, [4528-51-2] <small>((S)-isomer)</small>, [4528-52-3] <small>((S)-isomer, HCl)</small>
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| | ATC_prefix = N04
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| | ATC_suffix = BD01
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| | ATC_supplemental =
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| | PubChem = 26757
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| | DrugBank = APRD00525
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| | C=13 | H=17 | N=1
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| | molecular_weight = 187.281 g/mol
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| | bioavailability = 4.4%
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| | protein_bound = > 99.5%
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| | metabolism = liver
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| | elimination_half-life = 2 hours
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| | pregnancy_category = C <small>([[US]])</small>
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| | legal_status = prescription only (unscheduled) <small>([[US]])</small>
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| | routes_of_administration = Oral, [[transdermal]]ly
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| }}
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| '''Selegiline''' (l-deprenyl, Eldepryl® or Anipryl® [[veterinary]]) is a [[medication|drug]] used for the treatment of early-stage [[Parkinson's disease]] and [[senile dementia]]. In normal clinical doses it is a selective irreversible [[MAOI#Mode of action|MAO-B inhibitor]], however in larger doses (>20 [[milligram|mg]] in a typical adult) it loses its specificity and also inhibits MAO-A. Dietary restrictions are common for MAOI treatments, however, since selegiline is selective for MAO-B, special dietary restrictions for lower doses have been found to be unnecessary.<ref>
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| {{cite journal
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| | last = Amsterdam
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| | first = J. D.
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| | authorlink =
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| | coauthors =
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| | title = A double-blind, placebo-controlled trial of the safety and efficacy of selegiline transdermal system without dietary restrictions in patients with major depressive disorder
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| | journal = Journal of Clinical Psychiatry
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| | volume = 64
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| | issue = 2
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| | pages = 208-214
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| | publisher =
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| | date = 2003-02
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| | url =
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| | doi =
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| | id =
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| | accessdate = }}
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| </ref> The drug was researched by [[Joseph Knoll]]. Selegiline is most closely related to the [[phenylethylamines]]. The only difference between the two classes of drugs is the attachment of a [[propargyl]] group (three carbons with a triple bond between the second and third carbon) to the nitrogen.
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| ==Uses==
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| It is sometimes used [[off-label]] to treat [[narcolepsy]] and as a [[nootropic]], as well as for its published life-extending effects among several species of mammals. It is also reported to positively affect [[libido]], particularly in older [[male]]s. As of February 28, 2006, selegiline has also been approved by the [[Food and Drug Administration]] (FDA) to treat [[clinical depression|major depression]] using a transdermal patch ([[Emsam]] Patch).<ref>http://www.fda.gov/bbs/topics/NEWS/2006/NEW01326.html</ref> Selegiline is also used (at extremely high dosages relative to humans) in [[veterinary medicine]] to treat the symptoms of [[Cushing's disease]] and so-called "cognitive dysfunction" in [[dog]]s. As of June 26, 2006, a selegiline transdermal patch is being tested for its effectiveness in treating [[ADHD]].
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| Several clinical studies are currently underway to evaluate Selegiline's effectiveness in helping people stop smoking [[tobacco]] or [[cannabis (drug)|marijuana]].<ref>{{cite web
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| | last =
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| | first =
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| | authorlink =
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| | coauthors =
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| | title =Effectiveness of Selegiline in Treating Marijuana Dependent Individuals
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| | work =ClinicalTrials.gov
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| | publisher =National Institute on Drug Abuse
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| | date =March 2005
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| | url =http://clinicaltrials.gov/show/NCT00218517
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| | format =
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| | doi =
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| | accessdate = 2007-2-16 }}</ref><ref>{{cite web
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| | last =
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| | first =
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| | authorlink =
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| | coauthors =
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| | title =Usefulness of Selegiline as an Aid to Quit Smoking
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| | work =ClinicalTrials.gov
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| | publisher =National Institute on Drug Abuse
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| | date =July 2004
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| | url =http://clinicaltrials.gov/show/NCT00129311
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| | format =
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| | doi =
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| | accessdate = 2007-2-16 }}</ref>
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| ==Mechanism of Action==
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| Selegiline is a selective inhibitor of MAO-B; MAO-B metabolizes dopamine.<ref>Katzung, Bertram G. Basic & Clinical Pharmacology. 9th Edition. 2004. page 453. Lange Medical Books - McGraw Hill Publishers.</ref> Selegiline exhibits little therapeutic benefit when used independently, but enhances and prolongs the anti-[[Parkinson's disease|Parkinson]] effects of [[levodopa]].<ref>Katzung. Page 453</ref>
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| ===Metabolites===
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| ====Desmethylselegiline====
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| Desmethylselegiline may have neuroprotective antiapoptotic properties. A large multicenter study suggests a decrease of in the disease progression of parkinsonism but may have reflected other symptomatic response.<ref>Katzung, Bertram G. Basic & Clinical Pharmacology. 9th Edition. 2004. page 453. Lange Medical Books - McGraw Hill Publishers.</ref>
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| ====L-methamphetamine====
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| Selegiline is partly [[Drug metabolism|metabolized]] to l-methamphetamine, a [[stereoisomer]] of [[methamphetamine]] ''[[in vivo]]''.<ref>{{cite journal |author=Engberg G, Elebring T, Nissbrandt H |title=Deprenyl (selegiline), a selective MAO-B inhibitor with active metabolites; effects on locomotor activity, dopaminergic neurotransmission and firing rate of nigral dopamine neurons |journal=J. Pharmacol. Exp. Ther. |volume=259 |issue=2 |pages=841-7 |year=1991 |pmid=1658311 |doi=}}</ref> This stereoisomer is not considered psychoactive and has little abuse potential. The stimulatory effect on locomotor activity and dopamine synthesis may be contributed to by the action of l-methamphetamine.
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| Due to this metabolite selegiline can cause false positives for [[amphetamine]]/[[methamphetamine]] on drug tests.
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| ==Legal Issues==
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| Possibly due to the structural similarity to illegal [[stimulant]]s, selegiline has been classified as a [[controlled substance]] in [[Japan]] and thus can only be obtained with a [[Medical prescription|prescription]] or special government license. Selegiline is not a controlled substance in the US but a prescription is required to obtain it.
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| ==EMSAM==
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| February 28, 2006 - The Food and Drug Administration approved Emsam (selegiline), the first skin (transdermal) patch for use in treating major depression. The once a day patch works by delivering selegiline, a monoamine oxidase inhibitor or MAOI, through the skin and into the bloodstream. At its lowest strength, Emsam can be used without the dietary restrictions that are needed for all oral MAO inhibitors that are approved for treating major depression. It comes in three sizes that deliver 6, 9, or 12 mg of selegiline per 24 hours. The patch is a matrix containing three layers consisting of a backing, and adhesive drug layer, and a release liner that is placed against the skin. EMSAM was developed by Somerset Pharmaceuticals, Inc. In December 2004, Bristol-Myers Squibb and Somerset entered into an agreement that provides Bristol-Myers Squibb with distribution rights to market EMSAM after approval in the United States.
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| ==References==
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| {{Reflist|2}}
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| ==External links==
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| * [http://www.lef.org/prod_hp/abstracts/deprenylabs.html Collection of Research Abstracts on Deprenyl]
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| * [http://www.imminst.org/forum/index.php?s=&act=ST&f=44&t=16293&st=0&#entry177446 An Interview with Dr. Joseph Knoll regarding longevity]
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| * [http://lef.org/magazine/mag96/sept96_versy6.html Deprenyl Improves Learning And Memory]
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| * [http://www.antiaging-magazine.com/news/news_1.html Deprenyl (Selegiline) Can Slow Parkinson's Disease Safely] According to the British Medical Journal
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| * [http://www.fda.gov/bbs/topics/NEWS/2006/NEW01326.html FDA Approves Emsam (Selegiline) as First Drug Patch for Depression]
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| {{Dopaminergic agents}}
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| {{Antidepressants}}
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| [[Category:Nootropics]]
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| [[Category:Monoamine oxidase inhibitors]]
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| [[Category:Antiparkinsonian agents]]
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| [[Category:Phenethylamines]]
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| [[de:Selegilin]]
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| [[hu:Szelegilin]]
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