Pargyline

Pargyline
Skeletal formula of pargyline
Ball-and-stick model of the pargyline molecule
Clinical data
Trade namesEutonyl; Eutron
Other namesMO-911; A-19120; Lopac-P-8013; NSC-43798; N-Methyl-N-propargylbenzylamine
MedlinePlusa682088
Routes of
administration		Oral[1][2]
ATC code
Pharmacokinetic data
Metabolites• N-Methylbenzylamine[3]
• N-Propargylbenzylamine[3]
• N-Methylpropargylamine[3]
• Benzylamine[3]
• Propiolaldehyde[3]
• Propargylamine[3]
• Benzaldehyde[3]
• Pargyline-N-oxide[3]
Identifiers
  • N-benzyl-N-methylprop-2-yn-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.275 Edit this at Wikidata
Chemical and physical data
FormulaC11H13N
Molar mass159.232 g·mol−1
3D model (JSmol)
  • C#CCN(C)Cc1ccccc1
  • InChI=1S/C11H13N/c1-3-9-12(2)10-11-7-5-4-6-8-11/h1,4-8H,9-10H2,2H3 checkY
  • Key:DPWPWRLQFGFJFI-UHFFFAOYSA-N checkY
  (verify)

Pargyline, sold under the brand name Eutonyl among others, is a monoamine oxidase inhibitor (MAOI) medication which has been used to treat hypertension (high blood pressure) but is no longer marketed.[4][5][6] It has also been studied as an antidepressant, but was never licensed for use in the treatment of depression.[7][8] The drug is taken by mouth.[1][2]

Side effects of pargyline include orthostatic hypotension among others.[1] It has the potential for serious food and drug interactions with sympathomimetic agents like tyramine that can result in hypertensive crisis.[1] Pargyline acts as a non-selective and irreversible inhibitor of the monoamine oxidases MAO-A and MAO-B.[6] The exact mechanism of the hypotensive effects of pargyline and other MAOIs is unclear.[9][10][11][12] Structurally, pargyline is a benzylamine derivative and is related to selegiline and clorgyline.[13][14][15]

Pargyline was first described in 1960[9][16][17] and was introduced for medical use in 1963.[18] It was available in the United States and the United Kingdom.[18][2][5] The clinical use of pargyline was limited due to its side effects and interactions.[1] The drug remained available in the United States as late as 2000.[5] However, it was fully discontinued worldwide by 2007.[19]

  1. ^ a b c d e Hayes AH, Schneck DW (May 1976). "Antihypertensive pharmacotherapy". Postgraduate Medicine. 59 (5): 155–162. doi:10.1080/00325481.1976.11714363. PMID 57611.
  2. ^ a b c Cite error: The named reference Drugs@FDA was invoked but never defined (see the help page).
  3. ^ a b c d e f g h Cite error: The named reference KoppakaThompsonChen2012 was invoked but never defined (see the help page).
  4. ^ Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 934. ISBN 978-1-4757-2085-3. Retrieved 11 August 2024.
  5. ^ a b c Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 795. ISBN 978-3-88763-075-1. Retrieved 2024-08-11.
  6. ^ a b Finberg JP (August 2014). "Update on the pharmacology of selective inhibitors of MAO-A and MAO-B: focus on modulation of CNS monoamine neurotransmitter release". Pharmacology & Therapeutics. 143 (2): 133–152. doi:10.1016/j.pharmthera.2014.02.010. PMID 24607445.
  7. ^ Cite error: The named reference KlineCooper1980 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Murphy1977 was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference Tipton2018 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Abrams1969 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference McDonald1988 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Mizgala1965 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference MortonHall2012 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference FowlerOrelandCallingham1981 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Miklya2014a was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Ford1961 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference BryantTorosdagSchvartz1961 was invoked but never defined (see the help page).
  18. ^ a b Cite error: The named reference GreenHaddadAronson2018 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference Pray2007 was invoked but never defined (see the help page).