Originator
Trenimon,Bayer
Uses
Alkylating reagent in mutation research.
Definition
ChEBI: A member of the class of 1,4-benzoquinones that is 1,4-benzoquinone in which three of the ring hydrogens are replaced by aziridin-1-yl groups.
Manufacturing Process
Under anaerobic conditions including an atmosphere of nitrogen, 104 ml (2.0
moles) of aziridine is added as a single portion with stirring to a suspension of
33.6 g (0.2 mole) of 2,6-dimethoxy-1,4-benzoquinone in 500 ml of absolute
methanol at a temperature of 0° to 5°C. After the addition has been 2,6-
dimethoxy-1,4-benzoquinone completed the external cooling of the reaction
vessel is replaced by a room temperature water bath and the mixture is
stirred at room temperature for 45 hours while a slow stream of nitrogen is
passed therethrough to preserve the anaerobic reaction conditions. It is found
that the yellow starting material, during this period, completely disappears
into solution and that a violet or purple substance together with a colorless
substance are formed as precipitated reaction products. This mixture of
precipitated products is removed by filtration at -20°C and the residue is
washed with a small quantity of cooled methanol. Then the mixture is dried in
a vacuum desiccator yielding about 30.4 g of mixed product. The mixed
product is extracted with benzene whereby the violet or purple colored
component passes into solution and the substantially colorless product
remains in a yield of about 16.0 g. The colorless 2,6-bis-aziridino-l,4-
benzohydroquinone so obtained melts with decomposition at about 221-222°C
with melting starting at about 200°C. It can be purified by recrystallization
from a of dioxane yielding snow-white crystals that decompose when heated at 222-224°C while starting to melt at 220°C.
The benzene extract of the colored reaction product is evaporated to dryness
under vacuum, yielding a residue melting at 161-162°C which is recrystallized
from 200 ml of ethyl acetate, filtered under suction at -20°C, washed with
cold methanol and thus yields about 11.5 g of a pure, purple-colored
crystalline 2,3,5-tris-aziridino-1,4-benzoquinone melting at 162.5-163°C.
Therapeutic Function
Antineoplastic
General Description
Purple needle-like crystals.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
trisethyleneiminoquinone is an amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Fire Hazard
Flash point data is not available for trisethyleneiminoquinone, but trisethyleneiminoquinone is probably combustible.
Safety Profile
Poison by
intraperitoneal, intravenous, and parenteral
routes. Experimental teratogenic and
reproductive effects. Questionable
carcinogen with experimental carcinogenic
data. Human mutation data reported. When
heated to decomposition it emits toxic
fumes of NOx. Used as a drug for the
treatment of neoplastic dseases.
