Codeweavers Crssover has a bottle for AdiIRC which installs all the necessary dependencies for .NET 4.5, seems to work pretty good on both MacOS and Linux.
Installing AdiIRC in Wine on 64 bit Ubuntu and macOS.
Wine is a Windows compatibility layer which allows you to run many Windows programs on Linux/macOS.
Winetricks is a script to help you install various Windows components and programs.
AdiIRC does NOT work in mono.
On Ubuntu/Debian Type:
apt-get install wine cabextract
If the wine version in your Ubuntu/Debian repository is old, you can get the lasted from https://wiki.winehq.org/Ubuntu.
On macOS type:
# If homebrew is not installed, type /usr/bin/ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)" # Then install Wine through homebrew brew install wine
Wine does not work well with running 64 bit .NET applications, so you must create a 32 bit wine folder.
Type:
WINEARCH=win32 WINEPREFIX=~/.wine32 winecfg
Type:
wget https://raw.githubusercontent.com/Winetricks/winetricks/master/src/winetricks chmod +x winetricks
If you downloaded the 32 bit .NET 4.5 version of AdiIRC, type:
WINEPREFIX=~/.wine32 ./winetricks dotnet45
If you downloaded the 32 bit .NET 2.0 version of AdiIRC, type:
WINEPREFIX=~/.wine32 ./winetricks dotnet20
After .NET is installed, you should be able to run AdiIRC by typing:
WINEPREFIX=~/.wine32 wine AdiIRC.exe
It's possible to skin Wine/Windows programs to look more native in a Linux environment, check https://askubuntu.com/questions/219791/improve-gui-appearance-of-wine-applications/756781 for examples.
There has been some success running Wine headless using xvfb through screen.
WINEARCH=win32 WINEPREFIX=~/.wine32 screen xvfb-run wine AdiIRC.exe
If you have glitches when selecting text in the text area, try changing the message font to another font, preferably a monospaced font.