Pheniprazine References

Pheniprazine
Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	BR: Class C1 (Other controlled substances)^[1] In general: uncontrolled
Identifiers
IUPAC name (1-Methyl-2-phenyl-ethyl)hydrazine
CAS Number	55-52-7^N
PubChem CID	5929
ChemSpider	5716^Y
UNII	37VKD7067M
ChEMBL	ChEMBL22498^Y
CompTox Dashboard ( EPA)	DTXSID6043838
ECHA InfoCard	100.000.215
Chemical and physical data
Formula	C₉H₁₄N₂
Molar mass	150.225 g·mol⁻¹
InChI InChI=1S/C9H14N2/c1-8(11-10)7-9-5-3-2-4-6-9/h2-6,8,11H,7,10H2,1H3^Y Key:VXTWEDPZMSVFEF-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Pheniprazine ( INN; also known as amphethydrazine and amphetamine hydrazide; brand names Catron and Cavodil; codename JB-516) is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine chemical class that was used as an antidepressant in the 1960s.^[2]^[3]^[4] It was also used in the treatment of angina pectoris and schizophrenia.^[5]^[6] Pheniprazine has been largely discontinued due to toxicity concerns such as jaundice, amblyopia, and optic neuritis.^[7]^[8]^[9]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Lear TE, Browne MW, Greeves JA (November 1962). "A controlled trial of cavodil (pheniprazine) in depression". The Journal of Mental Science. 108 (457): 856–58. doi: 10.1192/bjp.108.457.856. PMID 13928843.
^ 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. doi: 10.1016/0006-2952(86)90285-6. PMID 2870717.
^ Eberson LE, Persson K (July 1962). "Studies on Monoamine Oxidase Inhibitors. I. The Autoxidation of β-Phenylisopropylhydrazine as a Model Reaction for Irreversible Monoamine Oxidase Inhibition". Journal of Medicinal and Pharmaceutical Chemistry. 91 (4): 738–52. doi: 10.1021/jm01239a006. PMID 14056405.
^ Sandler G (March 1961). "Clinical evaluation of pheniprazine in angina pectoris". British Medical Journal. 1 (5228): 792–4. doi: 10.1136/bmj.1.5228.792. PMC 1953879. PMID 13746179.
^ Wickstrom L, Hahn N (September 1962). "[beta-Phenylisoprophlhydrazine (Catran) in schizophrenia]". Nordisk Medicin. 68: 1165–7. PMID 14000469.
^ Fentem PH, Howitt G (December 1961). "Fatal jaundice after administration of pheniprazine". British Medical Journal. 2 (5267): 1616–7. doi: 10.1136/bmj.2.5267.1616. PMC 1970739. PMID 13892290.
^ Frandsen E (1962). "Toxic amblyopia during antidepressant treatment with pheniprazine (Catran)". Acta Psychiatrica Scandinavica. 38 (1): 1–14. doi: 10.1111/j.1600-0447.1962.tb01780.x. PMID 13894598. S2CID 35152293.
^ Thomsen NJ (January 1963). "[Optic neuritis after treatment with Catran]". Ugeskrift for Laeger. 125: 138–9. PMID 13981222.

Antidepressants ( N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine^‡ Bupropion Nomifensine^‡
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine^‡ Gepirone Indeloxazine Flupentixol Ketamine^§ Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Pivagabine^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAsTooltip Tricyclic antidepressants	Amineptine^‡ Amitriptyline^# Amitriptylinoxide Amoxapine Butriptyline^‡ Clomipramine^# Demexiptiline^‡ Desipramine Dibenzepin Dimetacrine^‡ Dosulepin Doxepin Imipramine Imipraminoxide^‡ Iprindole^‡ Lofepramine Melitracen Metapramine^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine^‡ Protriptyline Quinupramine^‡ Tianeptine Trimipramine
TeCAsTooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Isoniazid^# Linezolid^# Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tedizolid Tranylcypromine Reversible: Caroxazone^‡ Mixed: Bifemelane
MAO_ATooltip Monoamine oxidase A-selective	Reversible: Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone
MAO_BTooltip Monoamine oxidase B-selective	Irreversible: Selegiline

Adjunctive therapies
Atypical antipsychotics ( aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium ( lithium carbonate, lithium citrate) Thyroid hormones ( triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous
Ademetionine ( SAMe) GABAkine neurosteroids ( brexanolone, zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan ( 5-HTP) Rubidium chloride (RbCl) Tryptophan

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

v t e Anxiolytics ( N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids ( α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics ( Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^# WHO-EM ^‡ Withdrawn from market Clinical trials: ^† Phase III ^§Never to phase III

Monoamine metabolism modulators

Non-specific

AAAD

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

MAO

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

Hydrazines

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