Bringing medication that I don't have a prescription to on a plane and taking it overseas?

There are absolutely no rules against bringing any medication, prescription or over the counter. The TSA recommends you always carry medication in your carry-on bag. It does not need to be in the original bottle and you do not need to have the prescription with you. I am sure thousands of people take prescription drugs they do not have a prescription for in their luggage. The TSA looks for illegal drugs. They are not looking for prescription drugs, even if they are being used by a person without a prescription. See site below and scroll down to section in Medications.

There's no problems with taking over the counter or prescription pills. I took a month's worth of birth control pills in my carry on last summer, and there was no problem.

The TSA (or whoever) are looking for organic substances like weed and cocaine (basically controlled substances), and not for synthetic drugs like what you might expect from over the counter or prescription anxiety drugs. Basically, as I understand it, over the counter & prescription drugs will look different on any scans that your carry-on bag goes through. They'll only be suspicious if they find organic substances.

The only thing I do recommend is putting them in your carry on. If you rely on them, it's always best to keep them with you, and not put them in your checked luggage, as checked luggage is more likely to go missing than carry-on.

Pack it in your luggage and there will be no issues. I travel a lot and keep my pills in a daily pill thingy. I don't even bother brining the bottles, and I usually have the pill case in my carry on. I've NEVER had anyone ask me about them. And I fly maybe 5 -7 times a year.

And really, if it's for anxiety or something, who cares that a TSA agent knows.

One more thing, if they weren't prescribed to you, they are illegal for you to possess. There is no "loophole".