Structure via PubChem · Public domain (PubChem)
(−)-selegiline
Sign in to saveAlso 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 sectionsContents
- 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.