@Fawnya wrote:
As an addendum, the point you made in #4 is the most relevant and leads to the conclusion that I cannot claim this deduction as insurance paid for the medicine. Thanks for your help.
As long as the charity is registered in the US, it does not matter if they transferred the items out of the country after you donate them.
However, you are limited by the basis rule. That is, under most circumstances, you can only claim as a deduction, the amount of after-tax money you paid to acquire the property (your cost basis).
There are some rare types of insurance coverage that may be considered taxable, so if you paid tax on the insurance reimbursement for the drug, then you have a basis in the drug.
There is also an exception to the basis rule for capital property that was held for more than one year. It would be my opinion that even if you had these pills in your cabinet for more than a year until you discovered a way to donate them, they aren't considered "capital property" for other reasons. But you might find an aggressive accountant who would suggest that you could treat it as capital property. Then you could claim a donation value of $5000 without a signature from the charity, or up to the fair market value if you get a signature from the charity on your form 8283 and the charity also files a form 8282 to report that they disposed of the drugs for an "exempt" purpose. (An exempt purpose would include providing the drug to a patient, but it might be difficult to get those forms and signatures.)
This is all in publication 526
https://www.irs.gov/pub/irs-pdf/p526.pdf
