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(−)-selegiline

Structure via PubChem · Public domain (PubChem)

EntityQ47495783· pop 30· linked from 2,141 articles

(−)-selegiline

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Also known as L-deprenyl, Selegiline, L-Deprenalin, Selegilina, Selegilinum

Key facts

Drug.ATC_suffix
BD01
Drug.verifiedrevid
464388442
Drug.image
Selegiline.svg
Drug.image_class
skin-invert-image
Drug.width
225px
Drug.image2
L-Deprenyl (Selegiline) 3D-Ball-and-Stick.png
Drug.image_class2
bg-transparent
Drug.width2
225px
Drug.pronounce
("seh-LEH-ji-leen")
Drug.tradename
Eldepryl, Emsam, others
Drug.MedlinePlus
a697046
Drug.pregnancy_AU
B2
Drug.pregnancy_US
C
Drug.legal_AU
S4
Drug.legal_BR
C1
Drug.legal_CA
Rx-only
Drug.legal_UK
POM
Drug.legal_US
Rx-only

via Wikipedia infobox

Chemical data

Formula
C13H17N
Molecular weight
187.28 g/mol
IUPAC name
(2R)-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
SMILES
C[C@H](CC1=CC=CC=C1)N(C)CC#C
InChIKey
MEZLKOACVSPNER-GFCCVEGCSA-N
XLogP
2.8
Polar surface area
3.2 Ų
H-bond donors
0
H-bond acceptors
1
Formal charge
0

via PubChem

~64 min read

Encyclopedic overview

50 sections
Contents
  • Medical uses
  • Parkinson's disease
  • Depression
  • Available forms
  • Contraindications
  • Side effects
  • Overdose
  • Interactions
  • Serotonin syndrome and hypertensive crisis
  • Cytochrome P450 inhibitors and inducers
  • Selegiline inhibition of cytochrome P450 enzymes
  • Other interactions
  • Pharmacology
  • Pharmacodynamics
  • Pharmacokinetics
  • Chemistry
  • Analogues
  • Synthesis
  • History
  • Society and culture
  • Names
  • Generic forms
  • Availability
  • Notable users
  • Fictional representations
  • Internet vendors
  • Presence in ecstasy
  • Doping in sport
  • Regulatory status
  • Non-medical use
  • Anti-aging and longevity
  • Nootropic or "smart drug"
  • Research
  • Depression
  • Social anxiety
  • ADHD
  • Motivational disorders
  • Addiction
  • Sexual dysfunction
  • Psychosis
  • Excessive sleepiness
  • Periodic limb movement disorder
  • Tardive dyskinedia
  • Dementia and stroke
  • Disorders of consciousness
  • Neurotoxicity
  • Other formulations
  • Veterinary use
  • References
  • External links

Selegiline, also known as L-deprenyl and sold under the brand names Eldepryl, Zelapar, and Emsam among others, is a medication which is used in the treatment of Parkinson's disease and major depressive disorder. It has also been studied and used off-label for a variety of other indications, but has not been formally approved for any other use. The medication, in the form licensed for depression, has modest effectiveness for this condition that is similar to that of other antidepressants. Selegiline is provided as a swallowed tablet or capsule or an orally disintegrating tablet (ODT) for Parkinson's disease and as a patch applied to skin for depression.

Side effects of selegiline occurring more often than with placebo include insomnia, dry mouth, dizziness, anxiety, abnormal dreams, and application site reactions (with the patch form), among others. At high doses, selegiline has the potential for dangerous food and drug interactions, such as tyramine-related hypertensive crisis (the so-called "cheese reaction") and risk of serotonin syndrome. However, doses within the approved clinical range appear to have little to no risk of these interactions. In addition, the ODT and transdermal patch forms of selegiline have reduced risks of such interactions compared to the conventional oral form. Selegiline has no known misuse potential or dependence liability and is not a controlled substance except in Japan.

Excerpted from Wikipedia’s “(−)-selegiline” article, available under the CC BY-SA 4.0 licence.

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