Metepa

Metepa
Names
IUPAC name
1-[Bis(2-methyl-1-aziridinyl)phosphoryl]-2-methylaziridine
Preferred IUPAC name
1,1′,1″-Phosphoryltris(2-methylaziridine)
Other names
Methaphoxide
Metapoxide
Methyl aphoxide
METEPA
Trimethylaziridinylphosphine oxide
MAPO
Tris(1,2-propylene)phosphoramide
Tris(2-methyl-1-aziridinyl)phosphine oxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.296 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C9H18N3OP/c1-7-4-10(7)14(13,11-5-8(11)2)12-6-9(12)3/h7-9H,4-6H2,1-3H3 checkY
    Key: AVUYXHYHTTVPRX-UHFFFAOYSA-N checkY
  • InChI=1/C9H18N3OP/c1-7-4-10(7)14(13,11-5-8(11)2)12-6-9(12)3/h7-9H,4-6H2,1-3H3
    Key: AVUYXHYHTTVPRX-UHFFFAOYAF
  • CC1CN1P(=O)(N2CC2C)N3CC3C
Properties[1]
C9H18N3OP
Molar mass 215.237 g·mol−1
Appearance Colorless liquid
Boiling point 90 to 92 °C (194 to 198 °F; 363 to 365 K) (0.15-0.3 mmHg)
Hazards
Lethal dose or concentration (LD, LC):
136 mg/kg (male rat, oral)[1]
213 mg/kg (female rat, oral)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Metepa is a chemosterilant, with the capability to restrict ovarian development.[2] Metepa can also result in carcinogenesis, in particular the formation of teratomas.[3] It a minor ingredient in certain solid rocket propellants.[4]

References

  1. ^ a b c Merck Index, 12th Edition, 5998
  2. ^ Morgan, Philip B; Labrecque, G. C (1964). "Effect of Tepa and Metepa on Ovarian Development of House Flies". Journal of Economic Entomology. 57 (6): 896–899. doi:10.1093/jee/57.6.896.
  3. ^ Gaines, T. B; Kimbrough, R. D (1966). "The sterilizing, carcinogenic and teratogenic effects of metepa in rats". Bulletin of the World Health Organization. 34 (2): 317–20. PMC 2475925. PMID 5296141.
  4. ^ "Ababil-100/Al Fat'h". GlobalSecurity.org. Archived from the original on 15 April 2019.

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