Pargyline

Pargyline
Clinical data


MedlinePlus	a682088
ATC code	C02KC01 (WHO) C02LL01 (WHO)
Identifiers
IUPAC name N-benzyl-N-methylprop-2-yn-1-amine
CAS Number	555-57-7^Y
PubChem (CID)	4688
IUPHAR/BPS	7262
DrugBank	DB01626^N
ChemSpider	4526^Y
UNII	9MV14S8G3E^Y
ChEMBL	CHEMBL673^Y
ECHA InfoCard	100.008.275
Chemical and physical data
Formula	C₁₁H₁₃N
Molar mass	159.23 g/mol
3D model (Jmol)	Interactive image
SMILES C#CCN(C)Cc1ccccc1
InChI InChI=1S/C11H13N/c1-3-9-12(2)10-11-7-5-4-6-8-11/h1,4-8H,9-10H2,2H3^Y Key:DPWPWRLQFGFJFI-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Pargyline (brand name Eutonyl) is an irreversible selective monoamine oxidase (MAO)-B inhibitor drug (IC₅₀ for MAO-A is 0.01152 µmol/L and for MAO-B is 0.00820 µmol/L)^[1]^[2] It was brought to market in the US and the UK by Abbott in 1963 as an antihypertensive drug branded "Eutonyl". It was one of several MAO inhibitors introduced in the 1960s including nialamide, isocarboxazid, phenelzine, and tranylcypromine.^[3]^:146^[4]^:60^[5]^[6] By 2007 the drug was discontinued^[7] and as of 2014 there were no generic versions available in the US.^[8] In addition to its actions as an MAOI, pargyline has been found to bind with high affinity to the I₂ imidazoline receptor (an allosteric site on the MAO enzyme).^[9]

References

↑ Fisar Z, Hroudová J, Raboch J (2010). "Inhibition of monoamine oxidase activity by antidepressants and mood stabilizers.". Neuro Endocrinol Lett. 31 (5): 645–56. PMID 21200377.
↑ Murphy DL, Karoum F, Pickar D, et al. (1998). "Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (clorgyline) or MAO-B (selegiline and pargyline)". J. Neural Transm. Suppl. 52: 39–48. doi:10.1007/978-3-7091-6499-0_5. PMID 9564606.
↑ Edward Shorter, A historical dictionary of psychiatry. Oxford University Press, Inc 2005. ISBN 0195176685
↑ William M. Wardell and Louis Lasagna. Regulation Drug Development (Evaluative Studies 21) American Enterprise Institute (1975) ISBN 0844731676
↑ Council on Drugs New Drugs and Developments in Therapeutics: Pargyline Hydrochloride (Eutonyl) JAMA. 1963;184(11):887. doi:10.1001/jama.1963.03700240079013.
↑ "Eutonyl and MAO inhibitors". Drug and Therapeutics Bulletin. 1 (15): 59–60. 15 November 1963. doi:10.1136/dtb.1.15.59. ISSN 1755-5248. Pargyline is promoted only for the treatment of hypertension, and not for depression.
↑ W. Steven Pray Interactions Between Nonprescription Products and Psychotropic Medications US Pharmacist. 2007;32(11):12-15.
↑ FDA Eutonyl in the Drugs@FDA Database Accessed July 19, 2014
↑ Critical Reviews in Neurobiology. CRC Press. 1995. p. 43.

Central

α₂ agonist	Clonidine Guanabenz Guanfacine Methyldopa^# Tiamenidine^‡

Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guanethidine Guanoclor Guanazodine Guanoxabenz Guanoxan

Imidazoline receptor agonist	Moxonidine Rilmenidine Tolonidine

Ganglion-blocking/nicotinic antagonist	Hexamethonium^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

MAOI	Pargyline^‡

Adrenergic uptake inhibitor	Bietaserpine Deserpidine Methoserpidine Rescinnamine Reserpine

Tyrosine hydroxylase inhibitor	Metirosine

Direct

α₁ blockers	Prazosin Indoramin Trimazosin Doxazosin Urapidil

Non-selective α blocker	Phentolamine

Serotonin antagonist	Ketanserin Lidanserin

Endothelin antagonist (for PH)	dual (Bosentan, Macitentan) selective (Ambrisentan, Sitaxentan)

DA precursors/prodrugs	Levodopa^# Melevodopa

DA receptor agonists	Apomorphine Bromocriptine Cabergoline Dihydroergocryptine Lisuride Pergolide Piribedil Pramipexole Ropinirole Rotigotine

MAO-B inhibitors	Rasagiline Selegiline

COMT inhibitors	Entacapone Tolcapone

AAAD inhibitors	Benserazide Carbidopa^#

Others

Common
(non-specific)

Inhibitors: Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine

Inhibitors: MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone

Inhibitors: MAO-B selective: Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl)

PAH	Inhibitors: 3,4-Dihydroxystyrene

TH	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

DBH	Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	Inhibitors: CGS-19281A SKF-64139 SKF-7698

COMT	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nitecapone Tolcapone

TPH	Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat

See also: Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake and release modulators • Monoamine neurotoxins

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