That's gonna depend upon caliber, brand of ammo, make of weapon and several other factors. I've seen factory suggestions of 2-4 times, but it's going to vary. As examples, there have been documented cases of primer deactivation (primer pellet fragmented, making ignition impossible) and the .40 S&W is very sensitive to bullet setback causing pressure problems.
What you need to do is inspect your round each and every time. Compare the OAL to a round that hasn't been chambered. If it's visibly shorter, discard it. You also need to look at the condition of the case rim and bullet. If the case rim looks like a puppy's been teething on it, toss it. If the bullet looks like it's been battered, toss it.
Figuring about $1 per round, is your life worth more than that?