Pheniprazine

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Pheniprazine
Pheniprazine.png
Clinical data
Trade names Catron, Cavodil
Other namesAmphetamine hydrazide; [1] α-Methylphenethylhydrazine; JB-516; α-Methylphenelzine; N-Aminoamphetamine
Routes of
administration 		Oral
ATC code
  • None
Legal status
Legal status
  • BR: Class C1 (Other controlled substances) [2]
  • In general: uncontrolled
Identifiers
  • (1-Methyl-2-phenyl-ethyl)hydrazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.215 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H14N2
Molar mass 150.225 g·mol−1
  • InChI=1S/C9H14N2/c1-8(11-10)7-9-5-3-2-4-6-9/h2-6,8,11H,7,10H2,1H3 Yes check.svgY
  • Key:VXTWEDPZMSVFEF-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Pheniprazine, formerly sold under the brand names Catron and Cavodil, is an irreversible and non-selective monoamine oxidase inhibitor (MAOI) of the hydrazine group that was used as an antidepressant to treat depression in the 1960s. [3] [4] [5] [6] It was also used in the treatment of angina pectoris and schizophrenia. [7] [8] Pheniprazine has been largely discontinued due to toxicity concerns such as jaundice, amblyopia, and optic neuritis. [9] [10] [11]

Contents

Pharmacology

Pheniprazine is a monoamine oxidase inhibitor (MAOI). [3]

Amphetamine has been detected as an active metabolite of pheniprazine in animals. [12] Pheniprazine produces amphetamine- and psychostimulant-like effects at high doses in animals. [13] The same is true of certain other MAOIs, including iproniazid, phenelzine, tranylcypromine, and pargyline, but not nialamide. [13] [14] [15]

Chemistry

Pheniprazine, also known as α-methylphenethylhydrazine, [1] is a phenethylamine, amphetamine, and hydrazine derivative.

It is a close analogue of phenelzine (phenethylhydrazine) and amphetamine (α-methylphenethylamine) and can also be referred to by synonyms including amphetamine hydrazide, [1] α-methylphenelzine, and N-aminoamphetamine.

Metfendrazine (α,N-dimethylphenethylhydrazine; N-methylpheniprazine) is the corresponding methamphetamine (N-methylamphetamine) analogue.

Society and culture

Names

Pheniprazine is the generic name of the drug and its INN Tooltip International Nonproprietary Name and BAN Tooltip British Approved Name. [3] It is also known by the former developmental code name JB-516. [3]

Related Research Articles

<span class="mw-page-title-main">Monoamine oxidase inhibitor</span> Type of medication

Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, especially for treatment-resistant depression and atypical depression. They are also used to treat panic disorder, social anxiety disorder, Parkinson's disease, and several other disorders.

α-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by chemists at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

<span class="mw-page-title-main">Phenelzine</span> Antidepressant

Phenelzine, sold under the brand name Nardil, among others, is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine family which is primarily used as an antidepressant and anxiolytic to treat depression and anxiety. Along with tranylcypromine and isocarboxazid, phenelzine is one of the few non-selective and irreversible MAOIs still in widespread clinical use.

<span class="mw-page-title-main">Phenethylamine</span> Organic compound, a stimulant in humans

Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation.

<span class="mw-page-title-main">Tranylcypromine</span> Irreversible non-selective MAO inhibitor Antidepressant drug

Tranylcypromine, sold under the brand name Parnate among others, is a monoamine oxidase inhibitor (MAOI). More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). It is used as an antidepressant and anxiolytic agent in the clinical treatment of mood and anxiety disorders, respectively. It is also effective in the treatment of ADHD.

<span class="mw-page-title-main">Selegiline</span> Monoamine oxidase inhibitor

Selegiline, also known as L-deprenyl and sold under the brand names Eldepryl, Zelapar, and Emsam among others, is a medication which is used in the treatment of Parkinson's disease and major depressive disorder. It has also been studied for a variety of other indications, but has not been formally approved for any other use. The medication in the form licensed for depression has modest effectiveness for this condition that is similar to that of other antidepressants. Selegiline is provided as a swallowed tablet or capsule or an orally disintegrating tablet (ODT) for Parkinson's disease and as a patch applied to skin for depression.

<span class="mw-page-title-main">Isocarboxazid</span> Antidepressant

Isocarboxazid is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class used as an antidepressant. Along with phenelzine and tranylcypromine, it is one of only three classical MAOIs still available for clinical use in the treatment of psychiatric disorders in the United States, though it is not as commonly employed in comparison to the others.

<span class="mw-page-title-main">Dopaminergic</span> Substance related to dopamine functions

Dopaminergic means "related to dopamine", dopamine being a common neurotransmitter. Dopaminergic substances or actions increase dopamine-related activity in the brain.

<span class="mw-page-title-main">Moclobemide</span> Antidepressant

Moclobemide, sold under the brand names Amira, Aurorix, Clobemix, Depnil and Manerix among others, is a reversible inhibitor of monoamine oxidase A (RIMA) drug primarily used to treat depression and social anxiety. It is not approved for use in the United States, but is approved in other Western countries such as Canada, the UK and Australia. It is produced by affiliates of the Hoffmann–La Roche pharmaceutical company. Initially, Aurorix was also marketed by Roche in South Africa, but was withdrawn after its patent rights expired and Cipla Medpro's Depnil and Pharma Dynamic's Clorix became available at half the cost.

<span class="mw-page-title-main">Iproniazid</span> Antidepressant

Iproniazid is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity. The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France until its discontinuation in 2015.

<span class="mw-page-title-main">Rasagiline</span> Chemical compound

Rasagiline, sold under the brand name Azilect among others, is a medication which is used in the treatment of Parkinson's disease. It is used as a monotherapy to treat symptoms in early Parkinson's disease or as an adjunct therapy in more advanced cases. The drug is taken by mouth.

<span class="mw-page-title-main">Pargyline</span> Chemical compound

Pargyline, sold under the brand name Eutonyl among others, is a monoamine oxidase inhibitor (MAOI) medication which has been used to treat hypertension but is no longer marketed. It has also been studied as an antidepressant, but was never licensed for use in the treatment of depression. The drug is taken by mouth.

<span class="mw-page-title-main">Monoamine oxidase B</span> Protein-coding gene in the species Homo sapiens

Monoamine oxidase B, also known as MAO-B, is an enzyme that in humans is encoded by the MAOB gene.

<span class="mw-page-title-main">Metfendrazine</span> Chemical compound

Metfendrazine, also known as methphendrazine, is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine family. It was investigated as an antidepressant, but was never marketed.

<span class="mw-page-title-main">Hydrazine (antidepressant)</span> Group of antidepressants

The hydrazine antidepressants are a group of non-selective, irreversible monoamine oxidase inhibitors (MAOIs) which were discovered and initially marketed in the 1950s and 1960s. Most have been withdrawn due to toxicity, namely hepatotoxicity, but a few still remain in clinical use.

<span class="mw-page-title-main">Octamoxin</span> Chemical compound

Octamoxin, also known as 2-octylhydrazine, is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant in the 1960s but is now no longer marketed.

<span class="mw-page-title-main">Amiflamine</span> Chemical compound

Amiflamine (FLA-336) is a reversible inhibitor of monoamine oxidase A (MAO-A), thereby being a RIMA, and, to a lesser extent, semicarbazide-sensitive amine oxidase (SSAO), as well as a serotonin releasing agent (SRA). It is a derivative of the phenethylamine and amphetamine chemical classes. The (+)-enantiomer is the active stereoisomer.

<span class="mw-page-title-main">Almoxatone</span> Chemical compound

Almoxatone (MD-780,236) is a selective and reversible inhibitor of MAO-B. It was patented as an antidepressant and antiparkinsonian agent but was never marketed.

<span class="mw-page-title-main">3,4-Dichloroamphetamine</span> Chemical compound

3,4-Dichloroamphetamine (DCA), is an amphetamine derived drug invented by Eli Lilly in the 1960s, which has a number of pharmacological actions. It acts as a highly potent and selective serotonin releasing agent (SSRA) and binds to the serotonin transporter with high affinity, but also acts as a selective serotonergic neurotoxin in a similar manner to the related para-chloroamphetamine, though with slightly lower potency. It is also a monoamine oxidase inhibitor (MAOI), as well as a very potent inhibitor of the enzyme phenylethanolamine N-methyl transferase which normally functions to transform noradrenaline into adrenaline in the body.

References

  1. 1 2 3 Sanan S, Vogt M (February 1962). "Effect of drugs on the noradrenaline content of brain and peripheral tissues and its significance". Br J Pharmacol Chemother. 18 (1): 109–127. doi:10.1111/j.1476-5381.1962.tb01155.x. PMC   1482167 . PMID   14496718. Pheniprazine (α-methylphenethylhydrazine; 1-phenyl-2-hydrazinopropane; amphetamine hydrazide) [...]
  2. ↑ 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.
  3. 1 2 3 4 Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 809. ISBN   978-1-4757-2085-3 . Retrieved 12 August 2024.
  4. ↑ Lear TE, Browne MW, Greeves JA (November 1962). "A controlled trial of cavodil (pheniprazine) in depression". The Journal of Mental Science. 108 (457): 856–858. doi:10.1192/bjp.108.457.856. PMID   13928843.
  5. ↑ Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical Pharmacology. 35 (8): 1381–1387. doi:10.1016/0006-2952(86)90285-6. PMID   2870717.
  6. ↑ 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. 5 (4): 738–752. doi:10.1021/jm01239a006. PMID   14056405.
  7. ↑ Sandler G (March 1961). "Clinical evaluation of pheniprazine in angina pectoris". British Medical Journal. 1 (5228): 792–794. doi:10.1136/bmj.1.5228.792. PMC   1953879 . PMID   13746179.
  8. ↑ Wickstrom L, Hahn N (September 1962). "[beta-Phenylisoprophlhydrazine (Catran) in schizophrenia]". Nordisk Medicin. 68: 1165–1167. PMID   14000469.
  9. ↑ Fentem PH, Howitt G (December 1961). "Fatal jaundice after administration of pheniprazine". British Medical Journal. 2 (5267): 1616–1617. doi:10.1136/bmj.2.5267.1616. PMC   1970739 . PMID   13892290.
  10. ↑ 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.
  11. ↑ Thomsen NJ (January 1963). "[Optic neuritis after treatment with Catran]". Ugeskrift for Laeger. 125: 138–139. PMID   13981222.
  12. ↑ Baker GB, Coutts RT (1989). "Metabolism of monoamine oxidase inhibitors". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 13 (3–4): 395–403. doi:10.1016/0278-5846(89)90128-0. PMID   2664891.
  13. 1 2 Spencer PS (1977). "Review of the pharmacology of existing antidepressants". British Journal of Clinical Pharmacology. 4 (Suppl 2): 57S–68S. doi:10.1111/j.1365-2125.1977.tb05761.x. PMC   1429129 . PMID   334231.
  14. ↑ Kitanaka J, Kitanaka N, Takemura M (2006). "Modification of Monoaminergic Activity by MAO Inhibitors Influences Methamphetamine Actions". Drug Target Insights. 1: 19–28. doi:10.1177/117739280600100001. PMC   3155216 . PMID   21901055.
  15. ↑ Barbelivien A, Nyman L, Haapalinna A, Sirviö J (June 2001). "Inhibition of MAO-A activity enhances behavioural activity of rats assessed using water maze and open arena tasks". Pharmacology & Toxicology. 88 (6): 304–312. doi:10.1034/j.1600-0773.2001.880604.x. PMID   11453370.
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