Chemical Properties
Orange-yellow crystal. Melting point 226°C. Commonly used as its lactate (C15H15N3O-C3H6O3) = 343.38, [1837-57-6], called Rivanol. The lactate is a pale yellow crystal with a melting point of 253°C (226°F). It is soluble in 9 parts boiling water, 15 parts cold water, and 110 parts ethanol at 22 °C. The aqueous solution is fluorescent yellow.
Originator
Rivanol,Sopharma
Uses
7-ethoxyacridine-3,9-diamine is used in biological studies for cancer regression by inducing a regeneration-like response by activating expression and/or function of YAP and/or TAZ.
Definition
ChEBI: Ethacridine is a member of acridines.
Manufacturing Process
A mixture of 250 parts by volume of ethylene glycol, 50 parts by weight of 6-
nitro-9-chloro-2-ethoxyacridine (obtained by reaction of 52 parts by weight of
30 nitro-4-ethoxy-diphenylamine-6-carboxylic acid with phosphorous
oxychloride), 10 parts by weight of ammonium chloride, and 11 parts by
weight of urea were heated to 170°C and stirred for 1 hour at 170°-175°C.
Subsequently, the whole was cooled to 100°C, the reaction mixture was
introduced into 1000 parts by volume of water, rendered acidic to Congo
paper by means of hydrochloric acid and the 6-nitro-9-amino-2-ethoxyacridine
precipitated was filtered off. By reduction iron according to Bechamp, 6,9-
diamino-2-ethoxy-acridine hydrochloride was obtained with yield of 83% as
the yellow needles. The base was prepared by adding an equivalent of NaOH.
MP: 124°C.
In practice it is usually used as lactate.
Therapeutic Function
Antiseptic, Antibacterial
Purification Methods
It crystallises from 50% EtOH or EtOH as orange-yellow crystals. It also crystallises as a monohydrate m 116-118o. It has a pK2 0 of 11.04 in 50% aqueous EtOH. The methiodide is soluble in H2O and has m 332-334o (dec) (from aqueous Me2CO). [Albert & Gledhill J Soc Chem Ind 61 159 1942, Foye et al. J Pharm Sci 57 1795 1968, Albert & Goldacre J Chem Soc 708 1946, Beilstein 22 II 458, 22 III/IV 6679, 22/12 V 243.]
