Procarbazine hydrochloride

White to pale yellow crystalline powder with a slight odor mp, 233°C (dec).1 

Soluble in water sparingly soluble in most organic solvents.1 

Slowly oxidizes in aqueous solutions containing dissolved oxygen to azoprocarbazine and hydrogen peroxide.2 

Procarbazine is an alkylating agent that reacts with RNA.3,4 

Animal carcinogen. Reasonably anticipated to be a human carcinogen and when used as a chemotherapeutic agent in combination with nitrogen mustard, a potent animal carcinogen, can result in acute nonlymphocytic leukemia.5 Adverse effects in 50-70% of 

Chemical Name N-(1-Methylethyl)-4-[ (2-methylhydrazino)methyl] benzamide HCI Common Name Ibenmethyzin Structural Formula coNHCHfCHjij 

1 -Methyi-1 5-dicarbobenzoxyhydrazine Sodium hydroxide Hydrogen bromide 

Thionyl chloride Bromine Sodium hydride Isopropyl amine Hydrogen chloride 

544 grams of 4-methylbenzoic acid was boiled with 550 ml of thionyl chloride until a clear solution was obtained. After the excess thionyl chloride was distilled off, the residue was fractionated, yielding 605 g of 4-methylbenzoyl chloride BP 91°C/9 mm Hg, n =1.5532. 

This was dissolved in 550 ml of absolute benzene and the so-formed solution added to a mixture of 248 ml of absolute methanol and 550 ml of absolute benzene. After the exothermic reaction had terminated, the reaction mixture was boiled for a further 20 hours, then concentrated in vacuo and the product, 4-methylbenzoic acid methyl ester, isolated by conventional means. It could be purified by distillation, and the purified product boiled at 91°C/9 mm Hg, MP 32°C. 

Trade Name Manufacturer Country Year Introduced 

1 -Methyl-1 3-dlcarbobenzoxyhydrazlne Sodium hydroxide Hydrogen bromide 

---

Procainamide hydrochloride, 4,333 Procarbazine hydrochloride, 5,403 Promethazine hydrochloride, 5,429... 

Kelly MG et al Comparative carcinogenic-ity of -isopropyl- -(2 -methylhydrazino)-p-tolu-amide HCl (procarbazine hydrochloride), its degradation products, other hydrazines, and isonicotinic acid hydrazide. J Natl Cancer Inst 42 337-344, 1969... 

Various antineoplastics altretamine amsacrine 1-asparaginase dacarbazine melanoma theraccine porfimer sodium procarbazine hydrochloride topotecan hydrochloride tretinoin (dil-trans retinoic acid), systemic... 

Printing processes and printing inks Procarbazine hydrochloride... 

Hydrazines [(R)2-N-N-(R)2] do not readily hydrolyze. Procarbazine hydrochloride, which contains a hydrazine moiety, undergoes oxidation by atmospheric oxygen in the presence of moisture or in aqueous solution to form... 

Wear protective gloves, clothing, and goggles. Cover the spill with a 1 1 1 mixture by weight of soda ash, clay cat litter (bentonite), and sand. Scoop the mixture into a container. Estimate the amount of procarbazine hydrochloride, and add sufficient water to make an approximately 1% solution. For each 100 mg of procarbazine hydrochloride, add 6 g of calcium hypochlorite and stir at room temperature for 12 hours. Decant the liquid into the drain with a large volume of water, and treat the solid residue as normal refuse.1 6... 

---