So I hate to even go here, but most of the old time antler measures I've seen don't look simply "drilled", but rather have been carefully uniformly hollowed out tapering down to towards the tip. I wonder how those were made too.
That's because most of the old ones
weren't drilled, or at least not left as drilled. I've got notes on over 500 originals, and less than 3% were drilled and left that way.
Years ago, I picked up an antler measure like that with the intent of destroying it to see how it was made. A quick trip to Mr. Bandsaw to rip it down the middle, and I could see the tool marks inside. About 30 minutes later I had my own "uniformly hollowed out tapering down to towards the tip" antler powder measure (and most of that time was spent finding a good piece of antler).
Cut the antler to length, bore a hole in it the approximate length you want, and dunk the antler in boiling water for a few minutes. Then you just sort of scrape the "stuff" out with a long thin knife blade (yet another reason I prefer a "California" or "Turkish" clip blade on my pocket knife). This results in the same appearance and tool marks as I found on the undated original I destroyed, and on may others since then.
A couple of caveats: 1) It works better on fresher antler; with older antler, sometimes by the time the internal "stuff" is softened, the outside will absorb enough water that it will crack. 2) Try to hold it in the water so that the hole you bored is on top, and the antler is fully submerged; this seems to soften it up a bit more quickly. 3) Hollow it out before carving/shaping/etc the outside.
If you start running into stuff that isn't softened, just dunk it again.
Using fresh antler, I've never had one crack. Using "sheds" gathered in the spring, I typically get 1-2 cracking and unusable for every 10 I make.