Urea,N'-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(2-chloroethyl)-N-nitroso-,hydrochloride (1:1)

The Urea,N'-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(2-chloroethyl)-N-nitroso-,hydrochloride (1:1) with CAS registry number of 55661-38-6 is also known as N'-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-N-(2-chloroethyl)-N-nitrosourea hydrochloride. The IUPAC name is 3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-1-(2-chloroethyl)-1-nitrosourea hydrochloride. It belongs to product categories of Antitumors for Research and Experimental Use; Biochemistry. This chemical is a white to light yellow crystalline powder. In addition, the formula is C₉H₁₃ClN₆O₂.ClH and the molecular weight is 309.15.

Physical properties about Urea,N'-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(2-chloroethyl)-N-nitroso-,hydrochloride (1:1) are: (1)ACD/LogP: 0.19; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.09; (4)ACD/LogD (pH 7.4): 0.18; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 15.88; (8)ACD/KOC (pH 7.4): 29.73; (9)#H bond acceptors: 8; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 82Ų; (13)Flash Point: 239 °C; (14)Enthalpy of Vaporization: 74.84 kJ/mol; (15)Boiling Point: 471.6 °C at 760 mmHg; (16)Vapour Pressure: 2.72E-09 mmHg at 25 °C.

Preparation of Urea,N'-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(2-chloroethyl)-N-nitroso-,hydrochloride (1:1): add urea(1.5mol), 2-aminoethanol 92g (1.5mol) and DMF 750ml in the reaction flask. Stirred, heated and refluxed for 8 ~ 9h. Evaporate recovery DMF, then add 2-amino alcohol 66g (1.1mol) to residues under stirring for 2h. Thionyl chloride 195ml(319.4g, 2.68mol) was added dropwise under stirring at 0 °C, placed overnight. Heated to 100-120 °C and stirred for 2~3h, solids are precipitated. agglomerated material will be carefully broken up, filtered, washed, drained. Recrystallize with methanol to get 1,3-bis (2-chloroethyl) urea 86g. The yield is about 32%.

Uses of Urea,N'-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(2-chloroethyl)-N-nitroso-,hydrochloride (1:1): it is clinically used to relieve brain tumors, gastrointestinal tumors (stomach cancer, liver cancer, colorectal cancer), lung cancer, malignant lymphoma and chronic leukemia. Compared with similar alkylating agent products, this chemical has less toxicity, well water solubility for intravenous administration. This chemical can be used for treatment of intracranial tumors.

When you are using this chemical, please be cautious about it. As a chemical, it is toxic if swallowed. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. SMILES: Cl.ClCCN(N=O)C(=O)NCc1cnc(nc1N)C
2. InChI: InChI=1/C9H13ClN6O2.ClH/c1-6-12-4-7(8(11)14-6)5-13-9(17)16(15-18)3-2-10;/h4H,2-3,5H2,1H3,(H,13,17)(H2,11,12,14);1H
3. InChIKey: KPMKNHGAPDCYLP-UHFFFAOYAA
4. Std. InChI: InChI=1S/C9H13ClN6O2.ClH/c1-6-12-4-7(8(11)14-6)5-13-9(17)16(15-18)3-2-10;/h4H,2-3,5H2,1H3,(H,13,17)(H2,11,12,14);1H
5. Std. InChIKey: KPMKNHGAPDCYLP-UHFFFAOYSA-N

The toxicity data is as follows: