Poper, I contacted Digger from BottleBooks.com and this is what he said:
The bottle in question is New...it has the Federal Law Prohibits which dates it between 1932 and 1964 and clearly with a plastic cap it dates 1950-1964.
Here is some Trademark info:
Word Mark DOUGHERTY'S Goods and Services (CANCELLED) IC 033. US 049. G & S: Whiskey. FIRST USE: 18490000. FIRST USE IN COMMERCE: 18490000 Mark Drawing Code (1) TYPED DRAWING Serial Number 72150234 Filing Date August 1, 1962 Current Filing Basis 1A Original Filing Basis 1A Registration Number 0752240 Registration Date July 2, 1963 Owner (REGISTRANT) J. A. DOUGHERTY'S SONS, INC., DISTILLERS CORPORATION MARYLAND 1135 M. FRONT ST. PHILADELPHIA PENNSYLVANIA
(LAST LISTED OWNER) Medley Distilling Company CORPORATION KENTUCKY Owensboro KENTUCKY
Assignment Recorded ASSIGNMENT RECORDED Prior Registrations 0371835;0378141