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Pargyline
|
Systematic (IUPAC) name |
N-Benzyl-N-methylprop-2-yn-1-amine |
Clinical data |
MedlinePlus |
a682088 |
Pregnancy cat. |
? |
Legal status |
? |
Identifiers |
CAS number |
555-57-7 Y |
ATC code |
C02KC01 C02LL01 |
PubChem |
CID 4688 |
DrugBank |
DB01626 |
ChemSpider |
4526 Y |
UNII |
9MV14S8G3E Y |
ChEMBL |
CHEMBL673 Y |
Chemical data |
Formula |
C11H13N |
Mol. mass |
159.23 g/mol |
|
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
|
N (what is this?) (verify)
|
Pargyline (Eutonyl) is an irreversible monoamine oxidase B (MAO-B) inhibitor.[1] It has antihypertensive effects.[2]
Pharmacology[edit]
It functions by inhibiting the metabolism of catecholamines and tyramine within presynaptic nerve terminals. Patients taking pargyline must avoid concurrent consumption of tyramine-containing foods such as blue cheese and beer, as this can lead to a hypertensive crisis.[3]
References[edit]
- ^ 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. PMID 9564606.
- ^ Fuentes JA, Ordaz A, Neff NH (July 1979). "Central mediation of the antihypertensive effect of pargyline in spontaneously hypertensive rats". Eur. J. Pharmacol. 57 (1): 21–7. doi:10.1016/0014-2999(79)90099-2. PMID 477738.
- ^ Tulane University School of Medicine Department of Pharmacology: Autonomic Drug Profile handout, October 2006
Sympatholytic (and closely related) antihypertensives (C02)
|
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Sympatholytics
(antagonize α-adrenergic
vasoconstriction) |
Central
|
α2 agonist
|
- Clonidine
- Guanfacine
- Methyldopa #
|
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Adrenergic release inhibitors
|
- Bethanidine
- Bretylium
- Debrisoquine
- Guanadrel
- Guanazodine
- Guanethidine
- Guanoclor
- Guanoxan
- Guanazodine
- Guanoxabenz
- Guanoxan
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Imidazoline receptor agonist
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Ganglion-blocking/nicotinic antagonist
|
- Mecamylamine
- Pentolinium
- Trimethaphan
|
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Peripheral
|
Indirect
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MAOI
|
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Adrenergic uptake inhibitor
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- Bietaserpine
- Deserpidine
- Methoserpidine
- Rescinnamine
- Reserpine
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Tyrosine hydroxylase inhibitor
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Direct
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α1 blockers
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- Prazosin
- Indoramin
- Trimazosin
- Doxazosin
- Urapidil
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Non-selective α blocker
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Other antagonists |
Serotonin antagonist
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Endothelin antagonist (for PH)
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- dual (Bosentan)
- selective (Ambrisentan, Sitaxentan)
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
anat (a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot
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noco/syva/cong/lyvd/tumr, sysi/epon, injr
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proc, drug (C2s+n/3/4/5/7/8/9)
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Antiparkinson agents (N04)
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Dopaminergics |
DA precursors/prodrugs
|
- Etilevodopa
- Droxidopa
- Levodopa#
- Melevodopa
|
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DA receptor agonists
|
- Aplindore
- Apomorphine
- Bromocriptine
- Cabergoline
- Ciladopa
- Dihydroergocryptine
- Lisuride
- Pardoprunox
- Pergolide
- Piribedil
- Pramipexole
- Ropinirole
- Rotigotine
|
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MAO-B inhibitors
|
- Ladostigil
- Lazabemide
- Mofegiline
- Pargyline
- Rasagiline
- Selegiline
|
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COMT inhibitors
|
- Entacapone
- Nitecapone
- Tolcapone
|
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Aromatic L-amino acid decarboxylase inhibitors
|
- Benserazide
- Carbidopa#
- Methyldopa
|
|
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Anticholinergics |
- Benzatropine
- Biperiden#
- Bornaprine
- Chlorphenoxamine
- Cycrimine
- Dexetimide
- Dimenhydrinate
- Diphenhydramine
- Etanautine
- Etybenzatropine
- Mazaticol
- Metixene
- Orphenadrine
- Phenglutarimide
- Piroheptine
- Procyclidine
- Profenamine
- Trihexyphenidyl
- Tropatepine
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Others |
- Amantadine
- Budipine
- MDMA
- Memantine
- Methylxanthines
- Rimantadine
- UWA-101
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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|
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anat (n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp
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noco (m/d/e/h/v/s)/cong/tumr, sysi/epon, injr
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proc, drug (N1A/2AB/C/3/4/7A/B/C/D)
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Antidepressants (N06A)
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Specific reuptake inhibitors (RIs), enhancers (REs), and releasing agents (RAs)
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Selective serotonin reuptake inhibitors (SSRIs)
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- Alaproclate
- Citalopram
- Escitalopram
- Femoxetine
- Fluoxetine#
- Fluvoxamine
- Indalpine
- Ifoxetine
- Litoxetine
- Omiloxetine
- Panuramine
- Paroxetine
- Pirandamine
- Seproxetine
- Sertraline#
- Zimelidine‡
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Serotonin–norepinephrine reuptake inhibitors (SNRIs)
|
- Clovoxamine
- Desvenlafaxine
- Duloxetine
- Levomilnacipran
- Eclanamine
- Milnacipran
- Sibutramine
- Venlafaxine
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Serotonin–norepinephrine–dopamine reuptake inhibitors (SNDRIs)
|
- Amitifadine
- Bicifadine
- Brasofensine
- BTS-74,398
- Cocaine
- Diclofensine
- DOV-21,947
- DOV-102,677
- DOV-216,303
- EXP-561
- Fezolamine
- JNJ-7925476
- NS-2359
- PRC200-SS
- Pridefine
- SEP-225,289
- SEP-227,162
- Tesofensine
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Norepinephrine reuptake inhibitors (NRIs)
|
- Amedalin
- Atomoxetine/Tomoxetine
- Binedaline
- Ciclazindol
- Daledalin
- Edivoxetine
- Esreboxetine
- Lortalamine
- Mazindol
- Nisoxetine
- Reboxetine
- Talopram
- Talsupram
- Tandamine
- Viloxazine
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Dopamine reuptake inhibitors (DRIs)
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|
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Norepinephrine-dopamine reuptake inhibitors (NDRIs)
|
- Amineptine
- Bupropion/Amfebutamone#
- Cilobamine
- Manifaxine
- Methylphenidate
- Nomifensine
- Radafaxine
- Tametraline
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Norepinephrine-dopamine releasing agents (NDRAs)
|
- Amphetamine
- Befuraline
- Lisdexamfetamine
- Methamphetamine
- Phenethylamine
- Piberaline
- Tranylcypromine
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Serotonin-norepinephrine-dopamine releasing agents (SNDRAs)
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- 4-Methyl-αMT
- αET/Etryptamine
- αMT/Metryptamine
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Selective serotonin reuptake enhancers (SSREs)
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Others
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- Indeloxazine
- Teniloxazine
- Tramadol
- Viqualine
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Receptor antagonists and/or reuptake inhibitors
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Serotonin antagonists and reuptake inhibitors (SARIs)
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- Etoperidone
- Lubazodone
- Nefazodone
- Mepiprazole
- Trazodone
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Noradrenergic and specific serotonergic antidepressants (NaSSAs)
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- Aptazapine
- Esmirtazapine
- Mianserin
- Mirtazapine
- Setiptiline/Teciptiline
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Norepinephrine-dopamine disinhibitors (NDDIs)
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Serotonin modulators and stimulators (SMSs)
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Others
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Heterocyclic antidepressants (bi-, tri-, and tetracyclics)
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Bicyclics
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Tricyclics
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- Amezepine
- Amineptine
- Amitriptyline#
- Amitriptylinoxide
- Azepindole
- Butriptyline
- Cianopramine
- Clomipramine
- Cotriptyline
- Cyanodothiepin
- Demexiptiline
- Depramine/Balipramine
- Desipramine
- Dibenzepin
- Dimetacrine
- Dosulepin/Dothiepin
- Doxepin
- Enprazepine
- Fluotracen
- Hepzidine
- Homopipramol
- Imipramine
- Imipraminoxide
- Intriptyline
- Iprindole
- Ketipramine
- Litracen
- Lofepramine
- Losindole
- Mariptiline
- Melitracen
- Metapramine
- Mezepine
- Naranol
- Nitroxazepine
- Nortriptyline
- Noxiptiline
- Octriptyline
- Opipramol
- Pipofezine
- Propizepine
- Protriptyline
- Quinupramine
- Tampramine
- Tianeptine
- Tienopramine
- Trimipramine
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Tetracyclics
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- Amoxapine
- Aptazapine
- Azipramine
- Ciclazindol
- Ciclopramine
- Esmirtazapine
- Maprotiline
- Mazindol
- Mianserin
- Mirtazapine
- Oxaprotiline
- Setiptiline/Teciptiline
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Monoamine oxidase inhibitors (MAOIs)
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Nonselective
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- Irreversible: Benmoxin
- Carbenzide
- Cimemoxin
- Domoxin
- Echinopsidine
- Iproclozide
- Iproniazid
- Isocarboxazid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Safrazine
- Tranylcypromine
- Reversible: Caroxazone
- Paraxazone
- Quercetin
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MAOA-Selective
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- Reversible: Amiflamine
- Bazinaprine
- Befloxatone
- Berberine
- Brofaromine
- Cimoxatone
- Esuprone
- Eprobemide
- Harmala Alkaloids (Harmine
- Harmaline
- Tetrahydroharmine
- Harman
- Norharman, etc)
- Methylene Blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima
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MAOB-Selective
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- Irreversible: Ladostigil
- Mofegiline
- Pargyline
- Rasagiline
- Selegiline
- Reversible: Lazabemide
- Milacemide
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Azapirones and other 5-HT1A receptor agonists
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- Alnespirone
- Aripiprazole
- Befiradol
- Buspirone
- Eptapirone
- Flesinoxan
- Flibanserin
- Gepirone
- Ipsapirone
- Oxaflozane
- Tandospirone
- Vilazodone
- Zalospirone
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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dsrd (o, p, m, p, a, d, s), sysi/epon, spvo
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proc (eval/thrp), drug (N5A/5B/5C/6A/6B/6D)
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Dopaminergics
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Receptor ligands
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Agonists
|
- Adamantanes: Amantadine
- Memantine
- Rimantadine; Aminotetralins: 7-OH-DPAT
- 8-OH-PBZI
- Rotigotine
- UH-232; Benzazepines: 6-Br-APB
- Fenoldopam
- SKF-38,393
- SKF-77,434
- SKF-81,297
- SKF-82,958
- SKF-83,959; Ergolines: Bromocriptine
- Cabergoline
- Dihydroergocryptine
- Epicriptine
- Lisuride
- LSD
- Pergolide; Dihydrexidine derivatives: 2-OH-NPA
- A-86,929
- Ciladopa
- Dihydrexidine
- Dinapsoline
- Dinoxyline
- Doxanthrine; Others: A-68,930
- A-77636
- A-412,997
- ABT-670
- ABT-724
- Aplindore
- Apomorphine
- Aripiprazole
- Bifeprunox
- BP-897
- CY-208,243
- Dizocilpine
- Etilevodopa
- Flibanserin
- Ketamine
- Melevodopa
- Modafinil
- Pardoprunox
- Phencyclidine
- PD-128,907
- PD-168,077
- PF-219,061
- Piribedil
- Pramipexole
- Propylnorapomorphine
- Pukateine
- Quinagolide
- Quinelorane
- Quinpirole
- RDS-127
- Ro10-5824
- Ropinirole
- Rotigotine
- Roxindole
- Salvinorin A
- SKF-89,145
- Sumanirole
- Terguride
- Umespirone
- WAY-100,635
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Antagonists
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- Typical antipsychotics: Acepromazine
- Azaperone
- Benperidol
- Bromperidol
- Clopenthixol
- Chlorpromazine
- Chlorprothixene
- Droperidol
- Flupentixol
- Fluphenazine
- Fluspirilene
- Haloperidol
- Loxapine
- Mesoridazine
- Methotrimeprazine
- Nemonapride
- Penfluridol
- Perazine
- Periciazine
- Perphenazine
- Pimozide
- Prochlorperazine
- Promazine
- Sulforidazine
- Sulpiride
- Sultopride
- Thioridazine
- Thiothixene
- Trifluoperazine
- Triflupromazine
- Trifluperidol
- Zuclopenthixol; Atypical antipsychotics: Amisulpride
- Asenapine
- Blonanserin
- Cariprazine
- Carpipramine
- Clocapramine
- Clorotepine
- Clozapine
- Gevotroline
- Iloperidone
- Lurasidone
- Melperone
- Molindone
- Mosapramine
- Olanzapine
- Paliperidone
- Perospirone
- Piquindone
- Quetiapine
- Remoxipride
- Risperidone
- Sertindole
- Tiospirone
- Zicronapine
- Ziprasidone
- Zotepine; Antiemetics: AS-8112
- Alizapride
- Bromopride
- Clebopride
- Domperidone
- Metoclopramide
- Thiethylperazine; Others: Amoxapine
- Buspirone
- Butaclamol
- Ecopipam
- EEDQ
- Eticlopride
- Fananserin
- Hydroxyzine
- L-745,870
- Nafadotride
- Nuciferine
- PNU-99,194
- Raclopride
- Sarizotan
- SB-277,011-A
- SCH-23,390
- SKF-83,959
- Sonepiprazole
- Spiperone
- Spiroxatrine
- Stepholidine
- Tetrahydropalmatine
- Tiapride
- UH-232
- Yohimbine
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Reuptake inhibitors
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Plasmalemmal
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DAT inhibitors
|
- Piperazines: DBL-583
- GBR-12,935
- Nefazodone
- Vanoxerine; Piperidines: BTCP
- Desoxypipradrol
- Dextromethylphenidate
- Difemetorex
- Ethylphenidate
- Methylnaphthidate
- Methylphenidate
- Phencyclidine
- Pipradrol; Pyrrolidines: Diphenylprolinol
- MDPV
- Naphyrone
- Prolintane
- Pyrovalerone; Tropanes: Altropane
- Brasofensine
- CFT
- Cocaine
- Dichloropane
- Difluoropine
- FE-β-CPPIT
- FP-β-CPPIT
- Ioflupane (123I)
- Iometopane
- RTI-112
- RTI-113
- RTI-121
- RTI-126
- RTI-150
- RTI-177
- RTI-229
- RTI-336
- Tenocyclidine
- Tesofensine
- Troparil
- Tropoxane
- WF-11
- WF-23
- WF-31
- WF-33; Others: Adrafinil
- Armodafinil
- Amfonelic acid
- Amphetamine
- Amineptine
- Benzatropine
- Bromantane
- BTQ
- BTS-74,398
- Bupropion
- Ciclazindol
- Diclofensine
- Dimethocaine
- Diphenylpyraline
- Dizocilpine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- Etybenzatropine
- EXP-561
- Fencamine
- Fencamfamine
- Fezolamine
- GYKI-52,895
- Indatraline
- Ketamine
- Lefetamine
- Levophacetoperane
- LR-5182
- Manifaxine
- Mazindol
- Medifoxamine
- Mesocarb
- Modafinil
- Nefopam
- Nomifensine
- NS-2359
- O-2172
- Pridefrine
- Propylamphetamine
- Radafaxine
- SEP-225,289
- SEP-227,162
- Sertraline
- Sibutramine
- Tametraline
- Tedatioxetine
- Tripelennamine
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Vesicular
|
VMAT inhibitors
|
- Deserpidine
- Ibogaine
- Reserpine
- Tetrabenazine
|
|
|
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Allosteric modulators
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- Quinazolinamines: SoRI-9804
- SoRI-20040
- SoRI-20041
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Enzyme inhibitors
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Anabolism
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PAH inhibitors
|
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TH inhibitors
|
- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
|
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AAAD/DDC inhibitors
|
- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
|
|
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Catabolism
|
MAO inhibitors
|
- Nonselective: Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine; MAO-A selective: Amiflamine
- Bazinaprine
- Befloxatone
- Befol
- Brofaromine
- Cimoxatone
- Clorgiline
- Esuprone
- Harmala alkaloids
- Methylene Blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima; MAO-B selective: D-Deprenyl
- Ethanol
- L-Deprenyl (Selegiline)
- Ladostigil
- Lazabemide
- Milacemide
- Nicotine
- Pargyline
- Rasagiline
- Safinamide
|
|
COMT inhibitors
|
- Entacapone
- Nitecapone
- Tolcapone
|
|
DBH inhibitors
|
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Tropolone
|
|
|
|
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Others
|
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Precursors
|
- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa)
|
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Cofactors
|
- Ferrous iron (Fe2+)
- Tetrahydrobiopterin
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
|
|
Others
|
- Activity enhancers: BPAP
- PPAP; Toxins: 6-OHDA
|
|
|
|
List of dopaminergic drugs
|
|
UpToDate Contents
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English Journal
- The metabolism of histamine in rat hypothalamus and cortex after reserpine treatment.
- Maldonado M1, Maeyama K2.
- Neurochemistry international.Neurochem Int.2015 Jun-Jul;85-86:31-9. doi: 10.1016/j.neuint.2015.04.005. Epub 2015 Apr 29.
- The effect of reserpine on histamine (HA) and tele-methylhistamine (N(τ)-MHA) in hypothalamus and cortex of rats was analyzed and compared to catecholamines. IP injection of reserpine (5 mg/kg) confirmed the effectiveness of reserpine treatment on noradrenaline and dopamine levels. Our in-vitro e
- PMID 25936509
- Contribution of dopamine to mitochondrial complex I inhibition and dopaminergic deficits caused by methylenedioxymethamphetamine in mice.
- Barros-Miñones L1, Goñi-Allo B1, Suquia V1, Beitia G1, Aguirre N1, Puerta E2.
- Neuropharmacology.Neuropharmacology.2015 Jun;93:124-33. doi: 10.1016/j.neuropharm.2015.01.025. Epub 2015 Feb 7.
- Methylenedioxymethamphetamine (MDMA) causes a persistent loss of dopaminergic cell bodies in the substantia nigra of mice. Current evidence indicates that MDMA-induced neurotoxicity is mediated by oxidative stress probably due to the inhibition of mitochondrial complex I activity. In this study we i
- PMID 25666033
- D1 Antagonists and D2 Agonists Have Opposite Effects on the Metabolism of Dopamine in the Rat Striatum.
- Avila-Luna A1, Prieto-Leyva J, Gálvez-Rosas A, Alfaro-Rodriguez A, Gonzalez-Pina R, Bueno-Nava A.
- Neurochemical research.Neurochem Res.2015 May 17. [Epub ahead of print]
- The striatum is known to possess high levels of D1-like and D2-like receptors (D1Rs and D2Rs, respectively). We have previously shown that selective inhibition of D1Rs increases the dopaminergic metabolic response and proposed that this effect is associated with the concomitant activation of postsyn
- PMID 25981954
Japanese Journal
- Nicotine-Induced Noradrenaline Release From the Isolated Rat Stomach by Activation of L- and N-type Calcium Channels
- , , [他],
- The Japanese journal of pharmacology 83(2), 102-106, 2000-06-01
- … examined the effect of nicotine on the release of endogenous noradrenaline(NA)from the isolated, vascularly perfused rat stomach.The stomach was perfused via the coeliac artery with Krebs−Ringer solution containing 10 μM pargyline at a constant flow rate of 4 ml per minute.Nicotine was once applied in the perfusion medium for 2 min.Nicotine(10<SUP>-6</SUP>−10<SUP>-4</SUP>M)evoked NA release in a concentration−dependent manner.The nicotine(3×10<SUP>-5</SUP>M)−evoked NA release was abolished by hexamethonium …
- NAID 10007366853
- Involvement of Multiple Copper/Topa Quinone-Contanining and Flavin-Containing Amine Oxidases and NAD(P)^+ Aldehyde Dehydrogenases in Amine Degradation by Filamentous Fungi
- Frebort Ivo,Matsushita Kazunobu,Adachi Osao
- Journal of fermentation and bioengineering 84(3), 200-212, 1997-09-25
- … However, the enzymatic activities of extracts that contained non-coopper amine oxidases was substantially decreased by pargyline, an inhibitor specific to flavin-containing amine oxidases. …
- NAID 110002682599
- 第18回カテコールアミンと循環器系研究会 心臓交感神経刺激時の心筋間質ノルエピネフリン動態に影響を及ぼす交感神経終末機能の解析
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- Buy Pargyline hydrochloride (CAS 306-07-0), a selective and irreversible MAO-B inhibitor, from Santa Cruz. Purity: >98%, MF: C11H13N HCl, MW: 195.69 ... Appearance: Powder Physical State: Solid Solubility: Soluble in water (5 ...
- forum Join the Word of the Day Mailing List For webmasters TheFreeDictionary Google Bing? Word / Article Starts with Ends with Text ... pargyline a monoamine oxidase inhibitor, used as the hydrochloride salt. pargyline Eutonyl ...
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- 英
- pargyline
- 関
- パルギリン