Iproniazid
Title: Iproniazid
CAS Registry Number: 54-92-2
CAS Name: 4-Pyridinecarboxylic acid 2-(1-methylethyl)hydrazide
Additional Names: isonicotinic acid 2-isopropylhydrazide; 1-isonicotinoyl-2-isopropylhydrazine; 1-isonicotinyl-2-isopropylhydrazine
Molecular Formula: C9H13N3O
Molecular Weight: 179.22
Percent Composition: C 60.31%, H 7.31%, N 23.45%, O 8.93%
Literature References: Monoamine oxidase inhibitor. Prepd by treating isoniazid with isopropyl bromide in abs alcohol in the presence of sodium: McMillan et al., J. Am. Pharm. Assoc. Sci. Ed. 42, 457 (1953). Alternate synthesis: Fox, Gibas, J. Org. Chem. 18, 994 (1953). Comprehensive description: F. Belal, H. Abdel-Aliem, Anal. Profiles Drug Subs. 20, 337-368 (1991).
Properties: Needles from benzene + ligroin, mp 112.5-113.5°. Freely sol in water, alcohol; pH of aq solns about 6.7.
Melting point: mp 112.5-113.5°
 
Derivative Type: Dihydrochloride
Molecular Formula: C9H13N3O.2HCl
Molecular Weight: 252.14
Percent Composition: C 42.87%, H 6.00%, N 16.67%, O 6.35%, Cl 28.12%
Properties: Rhomboid crystals from isopropanol, dec at 227-228°. Freely sol in water; aq solns are very acidic.
 
Derivative Type: Phosphate
CAS Registry Number: 305-33-9
Trademarks: Marsilid (Roche)
Molecular Formula: C9H13N3O.H3PO4
Molecular Weight: 277.21
Percent Composition: C 38.99%, H 5.82%, N 15.16%, O 28.86%, P 11.17%
Properties: White to slightly yellowish powder, melting range 175-184°. pH of a 5% soln: 2.7-3.6. uv spectrum: J. Kracmar, J. Kracmarova, Pharmazie 34, 27 (1979). uv max (methanol): 265 nm (A1%1cm 166); (water): 264 nm (A1%1cm 176); (0.1N HCl): 267 nm (A1%1cm 179); (0.1N KOH): 244, 272, 308 nm (A1%1cm 113, 121, 135). Soly at 25° (mg/ml): water ~188; methanol ~21; ethanol (96%) ~9; chloroform ~0.6; diethyl ether <0.1; hexane <0.1.
Melting point: melting range 175-184°
Absorption maximum: uv max (methanol): 265 nm (A1%1cm 166); (water): 264 nm (A1%1cm 176); (0.1N HCl): 267 nm (A1%1cm 179); (0.1N KOH): 244, 272, 308 nm (A1%1cm 113, 121, 135)
 
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Hydrazides/Hydrazines; Monoamine Oxidase Inhibitor.

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