Pheniprazine Explained

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.^{[1] [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]}

Pharmacology

Pheniprazine is a monoamine oxidase inhibitor (MAOI).

Amphetamine has been detected as an active metabolite of pheniprazine in animals.^[10] Pheniprazine produces amphetamine- and psychostimulant-like effects at high doses in animals.^[11] The same is true of certain other MAOIs, including iproniazid, phenelzine, tranylcypromine, and pargyline, but not nialamide.^{[12] [13]}

Chemistry

Pheniprazine, also known as α-methylphenethylhydrazine, 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, 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 and . It is also known by the former developmental code name JB-516.

Notes and References

1. Book: Elks, J. . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer US . 2014 . 978-1-4757-2085-3 . 12 August 2024 . 809.
2. Lear TE, Browne MW, Greeves JA . A controlled trial of cavodil (pheniprazine) in depression . The Journal of Mental Science . 108 . 457 . 856–858 . November 1962 . 13928843 . 10.1192/bjp.108.457.856 .
3. Fagervall I, Ross SB . Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors . Biochemical Pharmacology . 35 . 8 . 1381–1387 . April 1986 . 2870717 . 10.1016/0006-2952(86)90285-6 .
4. Eberson LE, Persson K . 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 . July 1962 . 14056405 . 10.1021/jm01239a006 .
5. Sandler G . Clinical evaluation of pheniprazine in angina pectoris . British Medical Journal . 1 . 5228 . 792–794 . March 1961 . 13746179 . 1953879 . 10.1136/bmj.1.5228.792 .
6. Wickstrom L, Hahn N . [beta-Phenylisoprophlhydrazine (Catran) in schizophrenia] . Nordisk Medicin . 68 . 1165–1167 . September 1962 . 14000469 .
7. Fentem PH, Howitt G . Fatal jaundice after administration of pheniprazine . British Medical Journal . 2 . 5267 . 1616–1617 . December 1961 . 13892290 . 1970739 . 10.1136/bmj.2.5267.1616 .
8. Frandsen E . Toxic amblyopia during antidepressant treatment with pheniprazine (Catran) . Acta Psychiatrica Scandinavica . 38 . 1 . 1–14 . 1962 . 13894598 . 10.1111/j.1600-0447.1962.tb01780.x . 35152293 .
9. Thomsen NJ . [Optic neuritis after treatment with Catran] . Ugeskrift for Laeger . 125 . 138–139 . January 1963 . 13981222 .
10. Baker GB, Coutts RT . Metabolism of monoamine oxidase inhibitors . Progress in Neuro-Psychopharmacology & Biological Psychiatry . 13 . 3–4 . 395–403 . 1989 . 2664891 . 10.1016/0278-5846(89)90128-0 .
11. Spencer PS . Review of the pharmacology of existing antidepressants . British Journal of Clinical Pharmacology . 4 . Suppl 2 . 57S–68S . 1977 . 334231 . 1429129 . 10.1111/j.1365-2125.1977.tb05761.x .
12. Kitanaka J, Kitanaka N, Takemura M . Modification of Monoaminergic Activity by MAO Inhibitors Influences Methamphetamine Actions . Drug Target Insights . 1 . 19–28 . 2006 . 21901055 . 3155216 . 10.1177/117739280600100001.
13. Barbelivien A, Nyman L, Haapalinna A, Sirviö J . Inhibition of MAO-A activity enhances behavioural activity of rats assessed using water maze and open arena tasks . Pharmacology & Toxicology . 88 . 6 . 304–312 . June 2001 . 11453370 . 10.1034/j.1600-0773.2001.880604.x.