It depends. If reported on your 1099-R, your insurance premiums will be reported in box 5. This must be entered manually on Schedule A. To deduct medical expenses, you must have expenses at least 10% of your AGI unless you are over 65, which is still 7 1/2%. However, you also must be itemizing deductions to see the benefit on your return. This website linked to the IRS provides additional information: 1099-R Pension and Annuity Income - IRS.gov (see the box 5 information in the blurb).
Some states do allow for a health insurance deduction. If your state does, you may see a benefit on your state taxes even though you may not on the federal return.
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