3105-97-3

Basic information

• Product Name: 1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE
• Synonyms: 1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE;ETRENOL;Etrenol(mesylate);Win 249-33;1-(2-diethylaminoethylamino)-4-methylol-thioxanthen-9-one;9H-Thioxanthen-9-one, 1-[[2-(diethylaMino)ethyl]aMino]-4-(hydroxyMethyl)-;1-((2-(diethylamino)ethyl)amino)-4-(hydroxymethyl)-9h-thioxanthen-9-on;1-((2-(diethylamino)ethyl)amino)-4-(hydroxymethyl)thioxanthen-9-one
• CAS NO: 3105-97-3
• Molecular Formula: C₂₀H₂₄N₂O₂S
• Molecular Weight: 356.48
• EINECS: 221-463-7
• Mol File: 3105-97-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 100.6-102.8°
• Boiling Point: 570.5°Cat760mmHg
• Flash Point: 298.9°C
• Appearance: /
• Density: 1.1269 (rough estimate)
• Vapor Pressure: 7.42E-14mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: −20°C
• PKA: pKa 3.40 (Uncertain)
• CAS DataBase Reference: 1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE(3105-97-3)
• EPA Substance Registry System: 1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE(3105-97-3)

Safety Data

• Hazard Codes: T
• Statements: 45-46-20/21/22
• Safety Statements: 53-36/37/39-45
• WGK Germany: 3
• RTECS: XO1590000
• Hazardous Substances Data: 3105-97-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3105-97-3 differently. You can refer to the following data:
1. Antischistosomal.
2. Hycanthone is the active metabolite of the anthelmintic prodrug Lucanthone (L473700), which is used in the treatment of schistosomiasis.

Definition

ChEBI: A thioxanthen-9-one compound having a hydroxymethyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. It was formerly used (particularly as the monomethanesulfonic acid salt) as a schistosomicide for individual or mass treatement of infection with Schistosoma haematobium and S. mansoni, but due to its toxicity and concern about possible carcinogenicity, it has been replaced by other drugs such as praziquantel.

General Description

Odorless canary yellow to yellow-orange crystalline powder. Bitter taste.

Air & Water Reactions

1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE may be sensitive to prolonged exposure to air and light. Highly soluble in water.

Reactivity Profile

1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE is very sensitive to acid. .

Fire Hazard

Flash point data for 1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE are not available; however, 1-[(2-[DIETHYLAMINO]ETHYL)AMINO]-4-[HYDROXYMETHYL]-9H-THIOXANTHEN-9-ONE is probably combustible.

Safety Profile

Poison by subcutaneous, intravenous, and intramuscular routes. Moderately toxic by ingestion. Experimental teratogenic effects. Human mutation data reported. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits very toxic fumes of NOx and SOx.

InChI:InChI=1/C20H24N2O2S/c1-3-22(4-2)12-11-21-16-10-9-14(13-23)20-18(16)19(24)15-7-5-6-8-17(15)25-20/h5-10,21,23H,3-4,11-13H2,1-2H3

Synthetic route

hycanthone (3105-97-3) + phenyl isocyanate (103-71-9) → hycanthone N-phenylcarbamate (3612-74-6)

Conditions	Yield
In dichloromethane	100%

hycanthone (3105-97-3) + acetic anhydride (108-24-7) → 4-acetoxymethyl-1-(2-diethylamino-ethylamino)-thioxanthen-9-one (3612-72-4)

Conditions	Yield
With pyridine	63%

acetamide (60-35-5) + hycanthone (3105-97-3) → N-[1-(2-diethylamino-ethylamino)-9-oxo-9H-thioxanthen-4-ylmethyl]acetamide

Conditions	Yield
With sulfuric acid In acetic acid at 140℃; for 0.166667h;	43%

hycanthone (3105-97-3) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]formamide (146537-03-3)

Conditions	Yield
With sulfuric acid In acetic acid at 140℃; for 0.166667h;	43%

hycanthone (3105-97-3) + methyl chloroformate (79-22-1) → hycanthone methyl carbonate (111324-59-5)

Conditions	Yield
With pyridine In dichloromethane	19%

Propyl isocyanate (110-78-1) + hycanthone (3105-97-3) → hycanthone N-propylcarbamate (111324-57-3)

Conditions	Yield
In dichloromethane

hycanthone (3105-97-3) + n-butyl isocyanide (111-36-4) → hycanthone N-butylcarbamate (111324-58-4)

Conditions	Yield
In dichloromethane

hycanthone (3105-97-3) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid 1-(2-diethylamino-ethylamino)-9-oxo-9H-thioxanthen-4-ylmethyl ester

Conditions	Yield
With pyridine for 1.5h; Ambient temperature;

hycanthone (3105-97-3) + HO-(2,6-naphthylidene)-C(NH)NHC(O)OCH2-(p-C6H4)-OCH2C(O)NHCH2-(polystyrene resin) → 6-[1-(2-diethylamino-ethylamino)-9-oxo-9H-thioxanthen-4-ylmethoxy]-naphthalene-2-carboxamidine

Conditions	Yield
Stage #1: hycanthone; HO-(2,6-naphthylidene)-C(NH)NHC(O)OCH2-(p-C6H4)-OCH2C(O)NHCH2-(polystyrene resin) With tributylphosphine; diamide; triethylamine In tetrahydrofuran; dichloromethane for 15h; Solid phase reaction; Stage #2: With trifluoroacetic acid In dichloromethane; water for 4h; Solid phase reaction;

hycanthone (3105-97-3) → 2-[1-(2-Diethylamino-ethylamino)-9-oxo-9H-thioxanthen-4-ylmethyl]-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 1.5 h / Ambient temperature 2: 80 percent / tetra-n-butylammonium bromide / dimethylformamide / 2 h / 100 °C View Scheme

hycanthone (3105-97-3) → C20H23N2O5S2(1-)

Conditions	Yield
With sulfotransferase; 3′-phosphoadenosine 5′-phosphosulfate

Downstream Products

• 3612-74-6 hycanthone N-phenylcarbamate 
• 3612-72-4 1-<2-(Diethylaminoethyl)amino>-4-acetoxymethylthioxanthen-9-on 

Relevant articles and documents

The synthesis of hycanthone

-