Metepa

{{Chembox

| Watchedfields = changed

| verifiedrevid = 442286837

| ImageFile =metepa.svg

| ImageSize =

| PIN = 1,1′,1″-Phosphoryltris(2-methylaziridine)

| IUPACName =1-[Bis(2-methyl-1-aziridinyl)phosphoryl]-2-methylaziridine

| OtherNames = Methaphoxide
Metapoxide
Methyl aphoxide
METEPA
Trimethylaziridinylphosphine oxide
MAPO
Tris(1,2-propylene)phosphoramide
Tris(2-methyl-1-aziridinyl)phosphine oxide

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 54938

| 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

| InChIKey = AVUYXHYHTTVPRX-UHFFFAOYAF

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = AVUYXHYHTTVPRX-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo =57-39-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9PB481H025

| PubChem =60976

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C19556

| SMILES =CC1CN1P(=O)(N2CC2C)N3CC3C

}}

|Section2={{Chembox Properties

| Properties_ref = Merck Index, 12th Edition, 5998

| C=9 | H=18 | N=3 | O=1 | P=1

| Appearance =Colorless liquid

| Density =

| MeltingPt =

| BoilingPtC = 90 to 92

| BoilingPt_notes = (0.15-0.3 mmHg)

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| LD50 = 136 mg/kg (male rat, oral)
213 mg/kg (female rat, oral)

}}

}}

Metepa is a chemosterilant, with the capability to restrict ovarian development.{{cite journal|title=Effect of Tepa and Metepa on Ovarian Development of House Flies|journal=Journal of Economic Entomology|volume=57|issue=6|pages=896–899|doi=10.1093/jee/57.6.896|year=1964|last1=Morgan|first1=Philip B|last2=Labrecque|first2=G. C}} Metepa can also result in carcinogenesis, in particular the formation of teratomas.{{cite journal|title=The sterilizing, carcinogenic and teratogenic effects of metepa in rats|journal=Bulletin of the World Health Organization|volume=34|issue=2|pages=317–20|pmid=5296141|pmc=2475925|year=1966|last1=Gaines|first1=T. B|last2=Kimbrough|first2=R. D}} It a minor ingredient in certain solid rocket propellants.{{cite web|url=https://www.globalsecurity.org/wmd/world/iraq/ababil.htm|title=Ababil-100/Al Fat'h|website=GlobalSecurity.org|archive-url=https://web.archive.org/web/20190415172938/https://www.globalsecurity.org/wmd/world/iraq/ababil.htm|archive-date=15 April 2019}}