Pheniprazine

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]

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)

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 INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.^[3] It is also known by the former developmental code name JB-516.^[3]