1837-57-6

Basic information

• Product Name: 6,9-DIAMINO-2-ETHOXYACRIDINE LACTATE
• Synonyms: 2-ETHOXY-6,9-DIAMINOACRIDINE LACTATE;ACRINOL;6,9-DIAMINO-2-ETHOXYACRIDINE LACTATE;ETHACRIDINE LACTATE;ETHODIN;RIVANOL;2,5-diamino-7-ethoxyacridinelactate;2-aethoxy-6,9-diaminoacridinlactat
• CAS NO: 1837-57-6
• Molecular Formula: C₃H₆O₃*C₁₅H₁₅N₃O
• Molecular Weight: 343.38
• EINECS: 217-408-1
• Product Categories: API's;Pharma
• Mol File: 1837-57-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 235°C
• Boiling Point: 478.66°C (rough estimate)
• Flash Point: 270.4 °C
• Appearance: White or almost white crystalline powder; none stink
• Density: 1.2764 (rough estimate)
• Vapor Pressure: 4.72E-11mmHg at 25°C
• Refractive Index: 1.5855 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 6,9-DIAMINO-2-ETHOXYACRIDINE LACTATE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,9-DIAMINO-2-ETHOXYACRIDINE LACTATE(1837-57-6)
• EPA Substance Registry System: 6,9-DIAMINO-2-ETHOXYACRIDINE LACTATE(1837-57-6)

Safety Data

• Hazardous Substances Data: 1837-57-6(Hazardous Substances Data)

Usage

Chemical Properties

Pale-yellow crystals. Slowly soluble in 15 parts water; soluble in 9 parts boiling water; soluble in 110 parts alcohol (22C). Solutions are yellow, fluorescent, and stable to boiling.

Originator

Rivanol,Sopharma

Uses

Different sources of media describe the Uses of 1837-57-6 differently. You can refer to the following data:
1. 2-Ethoxy-6,9-diaminoacridine Lactate is used in treating purulent-necrotic wounds of hooves in cattle.
2. Bactericide, surgical antisepsis, preparation of pure γ-globulin.

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

Safety Profile

Poison by subcutaneous, intraperitoneal, and intravenous routes. Experimental reproductive effects. An antiseptic. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C15H15N3O.C3H6O3/c1-2-19-10-4-6-13-12(8-10)15(17)11-5-3-9(16)7-14(11)18-13;1-2(4)3(5)6/h3-8H,2,16H2,1H3,(H2,17,18);2,4H,1H3,(H,5,6)

Synthetic route

ethacridine lactate (1837-57-6) → 6,9-Diamino-5-brom-2-ethoxy-acridin

Conditions	Yield
With N-Bromosuccinimide; acetic acid	85%

ethacridine lactate (1837-57-6) + acetic anhydride (108-24-7) → N-(9-amino-2-ethoxyacridin-6-yl)acetamide

Conditions	Yield
In acetic acid for 0.166667h;	84%

2,6-Diaminopyridine (141-86-6) + ethacridine lactate (1837-57-6) → H2O4S*C20H19N7O

Conditions	Yield
Stage #1: ethacridine lactate With sulfuric acid; sodium nitrite In water at 5℃; for 0.333333h; Stage #2: 2.6-diaminopyridine With sodium carbonate In water at 20℃; for 12h;	76.3%

ethacridine lactate (1837-57-6) + salicylaldehyde (90-02-8) → 5-[(E)-(9-amino-7-ethoxyacridin-3-yl)azo]-2-hydroxybenzaldehyde

Conditions	Yield
Stage #1: ethacridine lactate With sulfuric acid; sodium nitrite In water at 0 - 5℃; for 0.333333h; Stage #2: salicylaldehyde With sodium carbonate In water at 20℃; for 2h;	75%

2.6-dimethylphenol (576-26-1) + ethacridine lactate (1837-57-6) → 4-(9-Amino-7-ethoxy-3-acridinylazo)-2,6-dimethylphenol

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium nitrite 1) H2O, 0 deg C, 2) 5 deg C to 10 deg C; Yield given. Multistep reaction;

ethacridine lactate (1837-57-6) → 9-Amino-7-ethoxy-3-acridin-diazonium-ditetrafluoroborat

Conditions	Yield
With hydrogenchloride; tetrafluoroboric acid; sodium nitrite 1) H2O, 0 deg C, 2) H2O, 0 deg C; Yield given. Multistep reaction;

ethacridine lactate (1837-57-6) → 5-Iod-ethacridin (74165-94-9)

Conditions	Yield
With iodine; potassium iodide

ethacridine lactate (1837-57-6) → 3,9-Diamino-2,4-dibrom-7-ethoxy-acridin

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / N-bromosuccinimide, aq. AcOH 2: 60 percent / N-bromosuccinimide, aq. AcOH View Scheme

ethacridine lactate (1837-57-6) + 4-(methylamino)phenol sulphate (55-55-0) → 2C7H7NO*C15H15N3O

Conditions	Yield
With potassium iodate In methanol pH=3.1; aq. buffer;

ethacridine lactate (1837-57-6) + p-dimethylaminocinnamaldehyde (6203-18-5) → C37H37N5O

Conditions	Yield
With sulfuric acid In methanol

ethacridine lactate (1837-57-6) → 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[[5-[(E)-(9-amino-7-ethoxyacridin-3-yl)azo]-2-hydroxyphenyl]methyl]-N-[2-(dimethylamino)ethyl]pentanamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium nitrite; sulfuric acid / water / 0.33 h / 0 - 5 °C 1.2: 2 h / 20 °C 2.1: sodium cyanoborohydride; acetic acid; methanol / 0.5 h / 20 °C 3.1: triethylamine / N,N-dimethyl-formamide / 20 °C View Scheme

ethacridine lactate (1837-57-6) → 4-[(E)-(9-amino-7-ethoxyacridin-3-yl)azo]-2-[[2-(dimethylamino)ethylamino]methyl]phenol hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium nitrite; sulfuric acid / water / 0.33 h / 0 - 5 °C 1.2: 2 h / 20 °C 2.1: sodium cyanoborohydride; acetic acid; methanol / 0.5 h / 20 °C View Scheme

ethacridine lactate (1837-57-6) → 4-[(E)-(9-amino-7-ethoxyacridin-3-yl)azo]-2-[[2-(dimethylamino)ethylmethylamino]methyl]phenol

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium nitrite; sulfuric acid / water / 0.33 h / 0 - 5 °C 1.2: 2 h / 20 °C 2.1: sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 20 °C View Scheme

2,6-Diaminopyridine (141-86-6) + ethacridine lactate (1837-57-6) → C20H19N7O*(x)ClH

Conditions	Yield
Stage #1: ethacridine lactate With sulfuric acid; sodium nitrite In water at 5℃; for 0.333333h; Stage #2: 2.6-diaminopyridine With sodium carbonate In water at 20℃; for 12h;