You have three loaded .22 caliber long rifle cartridges, above them is what looks like a .38 wad cutter target bullet,
you brass has been identified, but mid 1800's is too early. I'm not an expert, but my swag is turn of the century. There were rifles/carbines and pistols chambered for the same .44 cartridge, and they were popular with cowboys. The three bullets together look like two .38's which go back to the '20's until now, and one .45 pistol bullet that could date back to the 1870's until now.