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Would there be any advantage to using this to drive a headphone from the audio output jack of an iMac?
Hmmm if you're using iMac you're better off spending a tiny bit more and get an usb dac/amp.
That way you don't have to worry about battery also you're bypassing the iMac dac and letting the aftermarket dac/amp do its job.
The iMac already has a pretty good dac/amp so it's doubtful this would add anything.