4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide hydrochloride

• ChemBase ID: 73236
• Molecular Formular: C12H20ClN3O
• Molecular Mass: 257.7597
• Monoisotopic Mass: 257.12948996
• SMILES: c1(ccc(cc1)CNNC)C(=O)NC(C)C.Cl
• Canonical SMILES: CNNCc1ccc(cc1)C(=O)NC(C)C.Cl
• InChI: InChI=1S/C12H19N3O.ClH/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3;/h4-7,9,13-14H,8H2,1-3H3,(H,15,16);1H
• InChIKey: DERJYEZSLHIUKF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide hydrochloride
• IUPAC Traditional name: procarbazine hydrochloride
• Synonyms: N-(1-Methylethyl)-4-[(2-methylhydrazinyl)methyl]benzamide hydrochloride; Procarbazine hydrochloride; Matulane; rocarbazine hydrochloride; 4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide hydrochloride; N-(1-Methylethyl)-4-[(2-methylhydrazino)methyl]benzamide Hydrochloride; N-Isopropyl-(2-methylhydrazino)-p-toluamide Hydrochloride; Mutulane; Natulan; Procarbazine Hydrochloride

Database IDs

• CAS Number: 366-70-1
• EC Number: 206-678-6
• MDL Number: MFCD00072082
• PubChem SID: 162038156
• PubChem CID: 9703

CALCULATED PROPERTIES

• Acid pKa: 15.032636
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.6326173
• LogD (pH = 7.4): 0.97892106
• Log P: 0.9857342
• Molar Refractivity: 86.9783 cm^3
• Polarizability: 25.215479 Å^3
• Polar Surface Area: 53.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥18 mg/mL; Methanol; Water
• Apperance: Off-White Solid; white to tan powder
• Melting Point: 223-226°C
• Hydrophobicity(logP): -0.083

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-61-22-68
• Safety Statements: 53-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H341-H350-H360
• GHS Precautionary statements: P201-P281-P308 + P313
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: DNA/RNA

Product Information

• Purity: ≥98% (HPLC); 95%
• Salt Data: hydrochloride
• Empirical Formula (Hill Notation): C12H19N3O·HCl

DETAILS

Selleck Chemicals - S1995

Biological Activity:
Procarbazine hydrochloride (Matulane) is a hydrochloride salt form of procarbazine which is a polyfunctional alkylating compound used as an antineoplastic agent. Procarbazine is a cytostatic agent, meaning it strands cells midway through cell division, but it does not actively kill them. Procarbazine interferes with cells at a number of sites to prevent DNA and protein synthesis and mitosis. Procarbazine hydrochloride (Matulane) is used in the treatment of Hodgkin’s lymphoma and other malignant lymphomas including:- lymphosarcoma- reticulosarcoma- Brill-Symmers disease. Because procarbazine hydrochloride (Matulane) works differently to other anticancer agents,Procarbazine hydrochloride (Matulane) may be useful in the treatment of cancers that have not responded to other treatments. [1]References on Procarbazine HCl (Matulane)[1] http://en.wikipedia.org/wiki/Procarbazine, ,

Sigma Aldrich - SML0036

Biochem/physiol Actions
Procarbazine is an antineoplastic alkylating agent widely used in cancer chemotherapy in combination with other compounds. It has multiple mechanisms of action. Procarbazine inhibits protein, RNA and DNA synthesis in addition to being an alkylating agent.

Toronto Research Chemicals - P755400

Antineoplastic.

REFERENCES

• http://en.wikipedia.org/wiki/Procarbazine
• Rucki, R.J., et al.: Anal. Profiles Drug Subs., 5, 403 (1976)
• Massound, M., et al.: Eur. J. Cancer, 40, 1924 (1976)