Pheniprazine

Pheniprazine

Clinical data
Trade names	Catron, Cavodil
Other names	Amphetamine 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
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, 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]}

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]

References

1. 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. 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. 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.