Hexamethylphosphoramide
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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.
For research use only. We do not sell to patients.
- Purity: 99.86%
- CAS No.: 680-31-9
- Formula: C6H18N3OP
- Molecular Weight:179.20
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Hexamethylphosphoramide (0.2-10 mM; 1 h for DPXLs) undergoes cytochrome P-450-mediated N-demethylation in rat nasal microsomes to produce formaldehyde, induces DNA-protein crosslinks (DPXLs) in plasmid DNA-histone systems[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Hexamethylphosphoramide (10-4000 ppb; inhalation; 6 h/day, 5 days/week; 6-24 months) induces dose-dependent tracheitis, tracheobronchial epithelial degeneration in Charles-CD Sprague-Dawley rats, with keratinized squamous metaplasia in trachea at 4000 ppb[6].
Hexamethylphosphoramide (100-500 mg/kg; p.o.) induces reversible or irreversible sterility (aspermia) in male rats[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 680-31-9
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Appearance Liquid (Density: 1.03 g/mL)
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Molecular Weight 179.20
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Formula C6H18N3OP
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Color Colorless to light yellow
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SMILES
O=P(N(C)C)(N(C)C)N(C)C
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Synonyms
HMPA
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Solvent & Solubility
DMSO : 100 mg/mL (558.04 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Purity & Documentation
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Data Sheet (273 KB)
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SDS (640 KB)
- English - EN (640 KB)
- Français - FR (640 KB)
- Deutsch - DE (640 KB)
- Norwegian - NO (640 KB)
- Español - ES (640 KB)
- Swedish - SV (640 KB)
- Italian - IT (640 KB)
- Korean - KR (640 KB)
- Portuguese - PT (640 KB)
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Handling Instructions (2659 KB)
References
[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]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Complete Stock Solution Preparation Table
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 5.5804 mL | 27.9018 mL | 55.8036 mL | 139.5089 mL |
| 5 mM | 1.1161 mL | 5.5804 mL | 11.1607 mL | 27.9018 mL | |
| 10 mM | 0.5580 mL | 2.7902 mL | 5.5804 mL | 13.9509 mL | |
| 15 mM | 0.3720 mL | 1.8601 mL | 3.7202 mL | 9.3006 mL | |
| 20 mM | 0.2790 mL | 1.3951 mL | 2.7902 mL | 6.9754 mL | |
| 25 mM | 0.2232 mL | 1.1161 mL | 2.2321 mL | 5.5804 mL | |
| 30 mM | 0.1860 mL | 0.9301 mL | 1.8601 mL | 4.6503 mL | |
| 40 mM | 0.1395 mL | 0.6975 mL | 1.3951 mL | 3.4877 mL | |
| 50 mM | 0.1116 mL | 0.5580 mL | 1.1161 mL | 2.7902 mL | |
| 60 mM | 0.0930 mL | 0.4650 mL | 0.9301 mL | 2.3251 mL | |
| 80 mM | 0.0698 mL | 0.3488 mL | 0.6975 mL | 1.7439 mL | |
| 100 mM | 0.0558 mL | 0.2790 mL | 0.5580 mL | 1.3951 mL |
Hexamethylphosphoramide Related Classifications
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