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While I'm not a tax expert I've been in contact with this problem, and I offer you my opinion and the experience of people I know.
If you went to Canada to get a medication for which your doctor wrote a prescription, and you took that prescription to Canada to have it filled because the FDA has not yet approved the drug, then you should be fine for the cost of the drug and mileage and tolls to get there. If you went to Europe and the drug was available in Canada, you probably can't deduct the higher cost. A legal drug not covered by insurance should be fine. A new arthritis medication still in trials in the US would be an example. That drug would become available here in the future but you need it NOW and it would be a legitimate medical expense.
If you went to Mexico to get Laetrile for treatment of cancer, that one is iffy. I'd probably suggest take the deduction if you don't fear an audit; if audited you make the point that medications available in the US weren't working, and you believed the alternative medication gave you a chance. In this case probably the cancer victim is dead before the audit occurs so the problem is the heirs' rather than the victim's. That is a drug that has been around for a long time, the FDA believes it not effective, and there is no chance that it will be available in the US on a prescription basis any time soon.
If you went to Colombia to get an illegal drug, then no, no part of the cost, the transportation, nor the court costs to get out of jail when the customs people picked you up will be deductible.
Best wishes, Chris
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