k i looked this up
for one a item be it a bullet or cannon ball will reach it's terminal velocity at a height thats determined by it's weight so if you have a 22 that ways the same as a.223 it will reach it terminal velocity at the same distance
here is the definition of terminal velocity

In physics, terminal velocity is the velocity at which the air resistance force of a falling object equals the weight of the object minus the acting force due to air, which halts acceleration and causes speed to remain constant.
so two different bullets weighing the same will be just as deadly no matter how high it goes up because they weigh the same
even if the bullet goes twice as high it is just as deadly no more no Less then the bullet that goes half as high unless one of the, does not reach terminal velocity which they both will
the only thing that make the .223 any worst s it es higher and maybe farther but think about something your standing under a tree shooting near vertical the bullet wont go to far away from straight up it is more likely to get carried by the wind or jet stream

i got all my information from http://en.wikipedia.org/wiki/Terminal_velocity

it also shows how to figure the terminal velocity