The pics are still too small and unclear so I got nothing on the TRADE (monogram) MARK. The first picture you posted looks like a tooled double collar or whatever folk want to call it.
I'd say in the 1900-20 range.
The camera part is the worst, as you get better with that, more help will follow.
A whiskey or some hard liquor in almost assured. There were a few meds with similar form or reused bottles from local retailers though.