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Metepa

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Metepa
Names
IUPAC name 1--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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.296 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H18N3OP/c1-7-4-10(7)14(13,11-5-8(11)2)12-6-9(12)3/h7-9H,4-6H2,1-3H3Key: AVUYXHYHTTVPRX-UHFFFAOYSA-N
  • InChI=1/C9H18N3OP/c1-7-4-10(7)14(13,11-5-8(11)2)12-6-9(12)3/h7-9H,4-6H2,1-3H3Key: AVUYXHYHTTVPRX-UHFFFAOYAF
SMILES
  • CC1CN1P(=O)(N2CC2C)N3CC3C
Properties
Chemical formula C9H18N3OP
Molar mass 215.237 g·mol
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):
LD50 (median dose) 136 mg/kg (male rat, oral)
213 mg/kg (female rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

References

  1. ^ 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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