Thanks so much for the excellent photos, I can see exactly what you have now. These bottles of Mount Vernon Pure Rye Whiskey by the American Medicinal Spirits Company are hard to come by these days, so yours is quite a collectible item.
Unless one of the labels on the seals is legible, it's going to be hard to put an exact year on this bottle, but the main label looks to early 1930s, so it's getting up in age and, most importantly, dates from the Prohibition era or just shortly after. Prohibition (aka "the Noble Experiment") was enforced on June 30th, 1919 - the next day, July 1st, became known as the 'thirsty first'. The law of prohibition was repealed on 5th December 1933 and from then on it was up to individual states to enact their own laws for the control and use of alcohol. The last state to lift Prohibition was Mississippi which remained a dry state until 1966.
The National Distillers Products Corporation was one of the few distillers to prosper after Prohibition was lifted and they were kept 'alive' during prohibition by manufacturing for a bona fide marketing arm called the American Medicinal Spirits Company -as per the script on your bottle- as it was quite legal for doctors to prescribe alcohol for medicinal purposes.
Yours looks to be in fair condition, though the contents at half full suggest the seal may have been tampered with and re-waxed. The normal loss due to natural evaporation for a bottle this age would be shoulder height at the most.
Looking at recent comparables, this empty Mount Vernon bottle, with part of an original carton, sold on line in 2013 for $51 which is about representative. I would give yours an auction or eBay value in the range of $50 - $80.
It has a full retail or replacement value of $150 and is what you should insure it for.
I do hope this helps,
Please let me know if I can be of further assistance with any of the above, I would be glad to.