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
CAS Number	57-39-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	54938 ;
ECHA InfoCard	100.000.296
KEGG	C19556 ;
PubChem CID	60976;
UNII	9PB481H025 ;
CompTox Dashboard (EPA)	DTXSID5020815 ;
	InChI InChI=1S/C9H18N3OP/c1-7-4-10(7)14(13,11-5-8(11)2)12-6-9(12)3/h7-9H,4-6H2,1-3H3 Key: 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,4-6H2,1-3H3 Key: AVUYXHYHTTVPRX-UHFFFAOYAF;
	SMILES CC1CN1P(=O)(N2CC2C)N3CC3C;
Properties
Chemical formula	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):
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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

^ ^a ^b ^c Merck Index, 12th Edition, 5998
^ 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.
^ 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.
^ "Ababil-100/Al Fat'h". GlobalSecurity.org. Archived from the original on 15 April 2019.

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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
CAS Number	57-39-6^Y
3D model (JSmol)	Interactive image
ChemSpider	54938^Y
ECHA InfoCard	100.000.296
KEGG	C19556^Y
PubChem CID	60976
UNII	9PB481H025^Y
CompTox Dashboard (EPA)	DTXSID5020815
InChI InChI=1S/C9H18N3OP/c1-7-4-10(7)14(13,11-5-8(11)2)12-6-9(12)3/h7-9H,4-6H2,1-3H3^Y Key: AVUYXHYHTTVPRX-UHFFFAOYSA-N^Y 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
SMILES CC1CN1P(=O)(N2CC2C)N3CC3C
Properties^[1]
Chemical formula	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):
LD₅₀ (median dose)	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). Y verify (what is ^YN ?) Infobox references