Hexamethylphosphoramide

Hexamethylphosphoramide is an orally active polar aprotic solvent, flame retardant additive, and carcinogen. Hexamethylphosphoramide undergoes cytochrome P-450-mediated N-demethylation to Formaldehyde. Hexamethylphosphoramide induces DNA-protein crosslinks. Hexamethylphosphoramide has been linked to nasal tumors (squamous cell carcinoma, adenoid squamous cell carcinoma), squamous metaplasia, rhinitis, tracheitis, and reversible and irreversible infertility[1][2][3][4][5][6][7].

Product Specifications

CAS Number

[680-31-9]

Product Name Alternative

HMPA

UNSPSC

12352200

Hazard Statement

H314, H340, H350

Target

Biochemical Assay Reagents; Cytochrome P450; DNA Alkylator/Crosslinker

Type

Biochemical Assay Reagents

Related Pathways

Cell Cycle/DNA Damage; Metabolic Enzyme/Protease; Others

Field of Research

Cancer; Endocrinology; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/hexamethylphosphoramide.html

Purity

99.86

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=P(N(C)C)(N(C)C)N(C)C

Molecular Formula

C6H18N3OP

Molecular Weight

179.20

Precautions

H314, H340, H350

References & Citations

[1]Normant H. Hexamethylphosphoramide. Angewandte Chemie International Edition in English, 1967, 6 (12) : 1046-1067. |[2]Izquierdo-Gonzales S, et al. Hexamethylphosphoramide as a flame retarding additive for lithium-ion battery electrolytes. Journal of power sources, 2004, 135 (1-2) : 291-296. |[3]Ashby J, et al. Potentially carcinogenic analogues of the carcinogen hexamethylphosphoramide: evaluation in vitro. Br J Cancer. 1978 Sep;38 (3) :418-27. |[4]Kuykendall JR, et al. DNA-protein crosslink formation in rat nasal epithelial cells by hexamethylphosphoramide and its correlation with formaldehyde production. Mutat Res. 1995 Jul;343 (4) :209-18. |[5]Lee KP, et al. Metaplastic changes of nasal respiratory epithelium in rats exposed to hexamethylphosphoramide (HMPA) by inhalation. Am J Pathol. 1982 Jan;106 (1) :8-19. |[6]Lee KP, et al. Pulmonary response to inhaled hexamethylphosphoramide in rats. Toxicol Appl Pharmacol. 1982 Jan;62 (1) :90-103.|[7]Jackson H, et al. Antifertility action and metabolism of hexamethylphosphoramide. Nature. 1966 Oct 1;212 (5057) :86-7.