Alright, to start out...50-100 milligrams of benedryl isn't harmful. It contains the same chemical that is in a lot of OTC sleeping medications, which usually come in doses of 50-100 milligrams. That said, if there is no reason for you to be taking the drug, you really shouldn't be. It's not going to solve anything that's going on in your life. It's just going to end up making you feel more run-down and exhausted. Essentially, it's likely just making the depression worse. In terms of the self harm, you seem to already understand that it isn't the best idea. While it might feel good for the moment and relieve some of the pain you're experiencing...it's only going to make it worse in the long run. It isn't solving the root of the problem, nor is it helping with your depression. It's a coping method, but not a good one.
Aside from that, you are putting your life in danger. You seem to already recognize this, which is a bit troubling to me. Taking risks that put your life in danger are sometimes indicative of a desire to commit suicide. If you are ALL thinking of doing something like that, I seriously hope you reconsider and think about what you have going for you in life.
You definitely still have hop here and you can get through all of this. The fact that you're starting a therapy program is really good news. That can be tremendously helpful with a lot of people suffering from depression (as well as with SI). I know it's really hard right now but it definitely doesn't have to stay like this forever.