Metepa: Difference between revisions

(25 intermediate revisions by 12 users not shown)

Line 1:

{{Chembox

| Watchedfields = changed

| verifiedrevid = ~~434015333~~

| verifiedrevid =

|ImageFile=metepa ~~structure~~.~~png~~

|ImageFile=metepa.

|ImageSize=~~180px~~

|ImageSize=

⚫

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

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

⚫

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

⚫

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

⚫

|Section1= {{Chembox Identifiers

⚫

|OtherNames= aphoxide oxide (1,2-propylene)phosphoramide (2-methyl-1-aziridinyl)phosphine oxide

⚫

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

⚫

|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

Line 14:

Line 16:

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

| StdInChIKey = AVUYXHYHTTVPRX-UHFFFAOYSA-N

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

| CASNo=57-39-6

| PubChem=60976

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

| UNII = 9PB481H025

| PubChem =60976

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

| KEGG = C19556

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

}}

|Section2= {{Chembox Properties

|Section2={{Chembox Properties

| ~~Reference~~ = <ref name=Merck>''[[Merck Index]]'', 12th Edition, '''5998'''</ref>

| = <ref name=Merck>''[[Merck Index]]'', 12th Edition, '''5998'''</ref>

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

| Appearance=Colorless liquid

| Density=

| MeltingPt=

| BoilingPtC = 90 to 92

| BoilingPt=90-92 °C (0.15-0.3 mmHg)

| BoilingPt_notes = (0.15-0.3 mmHg)

| Solubility=

| Solubility =

}}

|Section3= {{Chembox Hazards

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

| Autoignition=

| LD50 = 136 mg/kg (male rat, oral)<ref name=Merck/> 213 mg/kg (female rat, oral)<ref name=Merck/>

}}

'''Metepa''' is a [[chemosterilant]], with the capability to restrict ovarian development.<ref>{{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}}</ref> Metepa can also result in [[carcinogenesis]], in particular the formation of [[teratomas]].<ref>{{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}}</ref> It a minor ingredient in certain [[solid-propellant rocket|solid rocket propellants]].<ref>{{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}}</ref>

'''Metepa''' is a [[chemosterilant]]. It is also used in [[creaseproof]]ing and [[flame retardant|flameproofing]] [[textile]]s.

==References==

Line 44:

Line 50:

[[Category:Flame retardants]]

[[Category:Pesticides]]

[[Category:~~Organophosphoric amides~~]]

[[Category:]]

[[Category:Aziridines]]