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Pheniprazine

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Pheniprazine
Clinical data
Trade namesCatron, Cavodil
Other namesAmphetamine hydrazide;[1] α-Methylphenethylhydrazine; JB-516; α-Methylphenelzine;N-Aminoamphetamine
Routes of
administration
Oral
ATC code
  • None
Legal status
Legal status
Identifiers
  • (1-Methyl-2-phenyl-ethyl)hydrazine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.215Edit this at Wikidata
Chemical and physical data
FormulaC9H14N2
Molar mass150.225 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 checkY
  • Key:VXTWEDPZMSVFEF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Pheniprazine, formerly sold under the brand namesCatron andCavodil, is anirreversible andnon-selectivemonoamine oxidase inhibitor (MAOI) of thehydrazine group that was used as anantidepressant to treatdepression in the 1960s.[3][4][5][6] It was also used in the treatment ofangina pectoris andschizophrenia.[7][8] Pheniprazine has been largely discontinued due totoxicity concerns such asjaundice,amblyopia, andoptic neuritis.[9][10][11]

Pharmacology

[edit]

Pheniprazine is amonoamine oxidase inhibitor (MAOI).[3]

Amphetamine has been detected as anactive metabolite of pheniprazine in animals.[12] Pheniprazine produces amphetamine- andpsychostimulant-like effects at high doses in animals.[13] The same is true of certain other MAOIs, includingiproniazid,phenelzine,tranylcypromine, andpargyline, but notnialamide.[13][14][15]

Chemistry

[edit]

Pheniprazine, also known as α-methylphenethylhydrazine,[1] is aphenethylamine,amphetamine, andhydrazinederivative.

It is a closeanalogue ofphenelzine (phenethylhydrazine) andamphetamine (α-methylphenethylamine) and can also be referred to by synonyms including amphetamine hydrazide,[1] α-methylphenelzine, andN-aminoamphetamine.

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

Society and culture

[edit]

Names

[edit]

Pheniprazine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name andBANTooltip British Approved Name.[3] It is also known by the former developmental code nameJB-516.[3]

References

[edit]
  1. ^abcSanan 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. Retrieved2023-08-16.
  3. ^abcdElks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 809.ISBN 978-1-4757-2085-3. Retrieved12 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. ^abSpencer 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.
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
5-HT1ARTooltip 5-HT1A receptoragonists
GABAARTooltip GABAA receptorPAMsTooltip positive allosteric modulators
Gabapentinoids
(α2δVDCCblockers)
Antidepressants
Sympatholytics
(Antiadrenergics)
Others
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
Related compounds
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