51219-90-0
Chemical Structure
Hexamethylphosphoramide-d18
- CAS No.: 51219-90-0
- Formula:C6D18N3OP
- Molecular Weight:197.31
InChIKey: GNOIPBMMFNIUFM-NBDUPMGQSA-N
SMILES: [2H]C([2H])([2H])N(C([2H])([2H])[2H])P(N(C([2H])([2H])[2H])C([2H])([2H])[2H])(N(C([2H])([2H])[2H])C([2H])([2H])[2H])=O
Biological Activity: Hexamethylphosphoramide-d18 is the deuterium labeled Hexamethylphosphoramide (HY-Y1155). 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][8].
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Hexamethylphosphoramide-d18 | Hexamethylphosphoramide-d18 is the deuterium labeled Hexamethylphosphoramide (HY-Y1155). 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]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216. [Content Brief]
- [2]. Normant H. Hexamethylphosphoramide. Angewandte Chemie International Edition in English, 1967, 6(12): 1046-1067.
- [3]. 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.
- [4]. 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]
- [5]. 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]
- [6]. 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]
- [7]. Lee KP, et al. Pulmonary response to inhaled hexamethylphosphoramide in rats. Toxicol Appl Pharmacol. 1982 Jan;62(1):90-103. [Content Brief]
- [8]. Jackson H, et al. Antifertility action and metabolism of hexamethylphosphoramide. Nature. 1966 Oct 1;212(5057):86-7. [Content Brief]
