N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) Chemical Properties

Melting point:

118-120 °C

Boiling point:

530℃

Density 

0.726

refractive index 

1.6200 (estimate)

Flash point:

275℃

storage temp. 

Inert atmosphere,2-8°C

solubility 

Acetone (Very Slightly), DMSO (Slightly), Methanol (Sparingly, Heated, Sonicated

pka

12.28±0.46(Predicted)

form 

Solid

color 

White to Off-White

CAS DataBase Reference

1477-57-2

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-40

Safety Statements 

24/25-45-36

Toxicity

LD50 orally in mice: >16000 mg/kg (Coulston)

MSDS

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N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

Win 18446 was shown to inhibit the biosynthesis of retinoic acid from retinol in neonatal and adult murine testis and in the embryonic murine gonad.

Definition

ChEBI: A carboxamide that is 1,8-diaminooctane in which a hydrogen attached to each of the amino groups has been replaced by a dichloroacetyl group. Inhibitor of aldehyde dehydrogenase 1a2 (ALDH1a2). Inhibits the biosynthesis of retinoic acid from retinol in neon tal and adult murine testis. It down-regulates sex related genes in zebrafish.

Biological Activity

win 18446 is a bis-(dichloroacetyl)-diamine which inhibits aldehyde dehydrogenase 1a2 (aldh1a2), with ic50 value of 300 nm [1].aldh1a2, expressed almost exclusively in the testes, localizes to developing germ cells within the seminiferous tubules and strongly binds retinol, but does not recognize acetaldehyde as a substrate, suggesting that aldh1a2 functions in testicular retinoic acid biosynthesis [1].in whole testes or germ cells isolated from mice at 2 days postpartum, win 18,446 alone (1 μm) or in combination with retinol significantly reduced the expression of stra8, a marker for retinoic acid activity [2].in male rabbits, oral administration of win 18446 at 200 mg/kg for 16 weeks substantially reduced intratesticular concentrations of retinoic acid, significantly impaired spermatogenesis, and resulted in infertility. reduced concentrations of intratesticular retinoic acid became obvious after only 4 weeks of treatment and preceded the decrease in sperm counts and the loss of mature germ cells in tissue samples. sperm counts and fertility recovered after treatment was discontinued [1].[1]. amory j k, muller c h, shimshoni j a, et al. suppression of spermatogenesis by bisdichloroacetyldiamines is mediated by inhibition of testicular retinoic acid biosynthesis. journal of andrology, 2011, 32(1): 111-119.[2]. hogarth c a, evanoff r, snyder e, et al. suppression of stra8 expression in the mouse gonad by win 18,446. biology of reproduction, 2011, 84(5): 957-965.

Safety Profile

Poison by intraperitoneal route.Human systemic effects by ingestion: nausea andvomiting. Human reproductive effects by ingestion:changes in spermatogenesis. An experimental teratogen.Other experimental reproductive effects. Human mutationdata reporte

storage

Store at +4°C

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