Pargyline

Chemical compound

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

ChEMBL

ChEMBL673^Y

CompTox Dashboard (EPA)

DTXSID3023423

ECHA InfoCard100.008.275

Chemical and physical dataFormulaC₁₁H₁₃NMolar mass159.232 g·mol⁻¹3D model (JSmol)

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 11.52 nM and for MAO-B is 8.20 nM)^[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)". MAO — the Mother of all Amine Oxidases. Journal of Neural Transmission. Supplement. Vol. 52. pp. 39–48. doi:10.1007/978-3-7091-6499-0_5. ISBN 978-3-211-83037-6. PMID 9564606. {{cite book}}: |journal= ignored (help)
^ 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. S2CID 220162992. 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.

Sympatholytic (and closely related) antihypertensives (C02)

Sympatholytics
(antagonize α-adrenergic
vasoconstriction)

Central

α₂-Adrenergic receptor agonists	Clonidine Guanabenz Guanfacine Guanoxabenz Methyldopa^# Tiamenidine^‡
Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guancydine Guanethidine Guanoclor Guanoxan
Imidazoline receptor agonists	Moxonidine Rilmenidine Tolonidine
Ganglion-blocking/nicotinic antagonists	Hexamethonium^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

Monoamine oxidase inhibitors	Pargyline^‡
VMAT inhibitors	Bietaserpine Deserpidine Methoserpidine Reserpine Syrosingopine
Tyrosine hydroxylase inhibitors	Metirosine

Direct

α₁-Adrenergic receptor blockers	Doxazosin Ketanserin Indoramin Prazosin Trimazosin Urapidil
Non-selective α-adrenergic receptor blockers	Phentolamine

Other antagonists

Serotonin receptor antagonists	Ketanserin Lidanserin
Endothelin receptor antagonists (for PHTooltip Pulmonary hypertension)	dual (Aprocitentan, Bosentan, Macitentan (+tadalafil)) selective (Ambrisentan, Sitaxentan)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Antiparkinson agents (N04)

Dopaminergics

DA precursors	Levodopa^# (+benserazide) Melevodopa
DA receptor agonists	Ergoline: Bromocriptine Cabergoline Dihydroergocryptine Lisuride Pergolide Non-ergoline: Apomorphine Piribedil Pramipexole Ropinirole Rotigotine Talipexole
MAO-B inhibitors	Rasagiline Safinamide Selegiline
COMT inhibitors	Entacapone Opicapone Tolcapone
AAAD inhibitors	Benserazide (+levodopa) Carbidopa^#

Anticholinergics

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Monoamine metabolism modulators

Non-specific

AAADTooltip Aromatic L-amino acid decarboxylase

Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAOTooltip Monoamine oxidase

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA Metanephrine→MHPG/VMA Norepinephrine (noradrenaline)→DHMA Normetanephrine→MHPG/VMA Dopamine→DOPAC 3-Methoxytyramine→HVA Serotonin→5-HIAA 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: Adarigiline Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl) Sembragiline

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone
DBHTooltip Dopamine beta-monooxygenase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors: CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products: Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin, melatonin)

TPHTooltip Tryptophan hydroxylase	Substrates→Products: Tryptophan→5-HTP Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat ethyl
AANATTooltip Serotonin N-acetyl transferase	Substrates→Products: Serotonin→N-Acetylserotonin
ASMTTooltip Acetylserotonin O-methyltransferase	Substrates→Products: N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase	Substrates→Products: L-Histidine→Histamine Inhibitors: Catechin Alpha-Fluoromethylhistidine Histidine methyl ester Meciadanol Naringenin Tritoqualine
HNMTTooltip Histamine N-methyltransferase	Substrates→Products: Histamine→N-Methylhistamine Inhibitors: Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91488 Tacrine
DAOTooltip Diamine oxidase	Substrates→Products: Histamine→Imidazole acetic acid Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins