Iproniazid

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Iproniazid
Systematic (IUPAC) name
N'-isopropylisonicotinohydrazide
Identifiers
CAS number 54-92-2
ATC code N06AF05
PubChem 3748
Chemical data
Formula C9H13N3O 
Mol. mass 179.219
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status

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Routes  ?

Iproniazid (Marsilid, Iprozid, Ipronid, Rivivol, Propilniazida) is a hydrazine drug that was previously used as an antidepressant.[1] It is an irreversible and nonselective monoamine oxidase inhibitor (MAOI).[2] It has been widely discontinued.

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[edit] History

Iproniazid was the first antidepressant ever marketed. It was originally intended for the treatment of tuberculosis.[1] In 1952, its antidepressant properties were discovered when researchers noted that the patients given iproniazid became "inappropriately happy".[1] It was subsequently developed as an antidepressant and was approved for use in 1958.[1] It was later withdrawn in 1961 due to the unacceptable incidence of hepatitis and was replaced by less hepatotoxic drugs like isocarboxazid (Marplan), phenelzine (Nardil), and tranylcypromine (Parnate).[1]

Iproniazid was developed using the same hydrazine that was used to power German V-2 rockets.[3]

[edit] References

  1. ^ a b c d e Robert A. Maxwell, Shohreh B. Eckhardt (1990). Drug discovery. Humana Press. p. 455. ISBN 0896031802, 9780896031807. 
  2. ^ Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical pharmacology 35 (8): 1381–7. PMID 2870717. http://linkinghub.elsevier.com/retrieve/pii/0006-2952(86)90285-6. 
  3. ^ [1]López-Muñoz F, Alamo C. Monoaminergic neurotransmission: the history of the discovery of antidepressants from 1950s until today. Curr Pharm Des. 2009;15(14):1563-86.
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Psychoanaleptics: antidepressants (N06A)
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Others: Inositol • Omega-3 Fatty Acids • S-Adenosyl-L-Methionine (SAMe)
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Dopaminergics
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Benzazepines: Fenoldopam • SKF 38393 • SKF 82958; Ergot-derivatives: Bromocriptine • Cabergoline • Dihydroergocryptine • Lisuride • LSD • Pergolide; Dihydrexidine-derivatives: A-86929 • Dihydrexidine • Dinapsoline • Dinoxyline • Doxathrine; Morphine-derivatives: Apomorphine • Propylnorapomorphine; Piperazines: Aripiprazole • Piribedil • WAY-100,635; Others: A-412,997 • Aplindore • Memantine • Pramipexole • Pukateine • Quinpirole • RDS-127 • Ropinirole • Rotigotine
Typical Antipsychotics: Acepromazine • Azaperone • Benperidol • Bromperidol • Clopenthixol • Chlorpromazine • Chlorprothixene • Droperidol • Flupentixol • Fluphenazine • Fluspirilene • Haloperidol • Loxapine • Mesoridazine • Methotrimeprazine • Molindone • Penfluridol • Perazine • Periciazine • Perphenazine • Pimozide • Prochlorperazine • Promazine • Sulforidazine • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Trifluperidol • Zuclopenthixol; Atypical Antipsychotics: Amisulpride • Asenapine • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Perospirone • Quetiapine • Risperidone • Sertindole • Sulpiride • Ziprasidone • Zotepine; Antiemetics: Alizapride • Bromopride • Clebopride • Domperidone • Metoclopramide • Thiethylperazine; Others: Amoxapine • Blonanserin • Buspirone • Butaclamol • N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline • Eticlopride • Fananserin • Mosapramine • Nafadotride • Nemonapride • Nuciferine • Raclopride • Remoxipride • SB-277,011-A • SCH 23390 • Spiperone • Spiroxatrine • Stepholidine • Tetrahydropalmatine • Tiapride • UH-232 • Yohimbine
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Piperazines: DBL-583 • GBR-12935 • Nefazodone • Vanoxerine; Piperidines: BTCP • Desoxypipradrol • Dextromethylphenidate • Ethylphenidate • HDMP-28 • Methylphenidate • Phencyclidine • Pipradrol; Pyrovalerones: MDPV • Pyrovalerone; Tropanes: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane • Lometopane • RTI-121 • RTI-126 • RTI-150 • RTI-336 • Tenocyclidine • Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 • WF-31 • WF-33; Others: Amfonelic Acid • Amineptine • Benztropine • Bromantane • BTQ • BTS 74,398 • Bupropion • Cypenamine • Diclofensine • Dimethocaine • Diphenylprolinol • Dizocilpine • DOV 102,677 • DOV 21,947 • DOV 216,303 • Ethcathinone • Fencamfamine • GYKI-52895 • Indatraline • Ketamine • Lefetamine • LR-5182 • Manifaxine • Mazindol • Medifoxamine • Mesocarb • Nisoxetine • Nomifensine • NS2359 • O-2172 • Prolintane • Radafaxine • SEP-225289 • SEP-227162 • Sibutramine • Tametraline • Tripelennamine
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Releasing
Agents
Alkylamines: Cyclopentamine • Propylhexedrine; Aminopropanes: Indanylaminopropane • Naphthylaminopropane; Oxazolines: 4-Methylaminorex • Aminorex • Pemoline; Phenethylamines: 4-Fluoroamphetamine • 4-Fluoromethamphetamine • Amphetamine • Amphetaminil • Amfepentorex • Benzphetamine • Butylone • Cathine • Cathinone • Clobenzorex • Dextroamphetamine • Diethylcathinone • Dimethylamphetamine • Dimethylcathinone • Ethylamphetamine • Ethylone • Fenethylline • Fenproporex • Flephedrone • Furfenorex • MBDB • MDA • MDEA • MDMA • Mefenorex • Mephedrone • Methamphetamine • Methcathinone • Methylone • Phendimetrazine • Phenethylamine • Phenmetrazine • PMA • PMEA • PMMA • Propylamphetamine • Tyramine • Xylopropamine; Piperazines: BZP • MBZP • MeOPP; Others: 4-Benzylpiperidine • Zylofuramine
Enzyme
Inhibitors
PAH Inhibitors
TH Inhibitors
Nonselective: Iproclozide • Iproniazid • Isocarboxazid • Nialamide • Phenelzine • Pheniprazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline
DBH Inhibitors
Others
Others
Activity Enhancers: BPAP • PPAP; Others: Amantadine • Memantine • Rimantadine
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