Iproniazid (brand/other names of Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, and irreversible monoamine oxidase inhibitor (MAOI). Monoamine oxidases is a family of FAD-containing enzymes and is an important target for antidepressant drugs. Iproniazid has been used as an antidepressive agent in many countries. It is a xenobiotic that was originally designed to treat tuberculosis, but was later found to act most prominently as an antidepressant drug. The medical use of iproniazid was discontinued in most of the world due to its hepatotoxicity, but remained in use in France until fairly recently.

Physicochemical Properties

Molecular Formula	C9H13N3O
Molecular Weight	179.22
Exact Mass	179.106
CAS #	54-92-2
Related CAS #	Iproniazid phosphate;305-33-9
PubChem CID	3748
Appearance	White to off-white solid powder
Melting Point	161-161.5
LogP	1.506
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Heavy Atom Count	13
Complexity	164
Defined Atom Stereocenter Count	0
InChi Key	NYMGNSNKLVNMIA-UHFFFAOYSA-N
InChi Code	InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13)
Chemical Name	N'-propan-2-ylpyridine-4-carbohydrazide
Synonyms	Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In vitro activity: Kinase Assay: Cell Assay:
ln Vivo
Animal Protocol
References	Molecules.2014 Nov 14;19(11):18620-31;https://en.wikipedia.org/wiki/Iproniazid
Additional Infomation	Iproniazid is a carbohydrazide and a member of pyridines. Withdrawn from the Canadian market in July 1964 due to interactions with food products containing tyrosine. An irreversible inhibitor of monoamine oxidase types A and B that is used as an antidepressive agent. It has also been used as an antitubercular agent, but its use is limited by its toxicity. Drug Indication For the treatment of depression (originally intended to treat tuberculosis). Pharmacodynamics Iproniazid is a monoamine oxidase inhibitor (MAOI) that was developed as the first anti-depressant.

Solubility Data

Solubility (In Vitro)

DMSO: >35 mg/mL Water:>35 mg/mL Ethanol:>35 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.95 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.95 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (13.95 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.5797 mL	27.8987 mL	55.7973 mL
	5 mM	1.1159 mL	5.5797 mL	11.1595 mL
	10 mM	0.5580 mL	2.7899 mL	5.5797 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.