680-31-9
Chemical Structure
Hexamethylphosphoramide
Synonym(s): HMPA
- CAS No.: 680-31-9
- Formula:C6H18N3OP
- Molecular Weight:179.20
InChIKey: GNOIPBMMFNIUFM-UHFFFAOYSA-N
SMILES: O=P(N(C)C)(N(C)C)N(C)C
Biological Activity: 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].
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Hexamethylphosphoramide | 99.86% | 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. | ||||||||||||||||||||
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References
- [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. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
- [6]. Lee KP, et al. Pulmonary response to inhaled hexamethylphosphoramide in rats. Toxicol Appl Pharmacol. 1982 Jan;62(1):90-103. [Content Brief]
- [7]. Jackson H, et al. Antifertility action and metabolism of hexamethylphosphoramide. Nature. 1966 Oct 1;212(5057):86-7. [Content Brief]
