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Antidepressant pharmacotherapy presents many challenges to clinicians dealing with patients suffering from chronic pain. Co-existent depression and pain continues to present clinicians with a plethora of difficult treatment selections. Treated in isolation, each of these disease states can prove difficult to treat. Collectively, depression and pain often present significantly more difficult challenges to the clinician. Antidepressants may be used as a primary treatment modality for depression in a patient dealing with chronic pain. At other times these agents may be used to treat certain specific chronic pain syndromes, possibly in the face of concomitant depression. Clinicians should be aware of the many peculiarities associated with this broad class of medications. Included in this review are considerations for drug selection, dose escalation, and common drug related problems (eg, adverse drug reactions). In addition, attention is paid to the appropriate selection of an agent for use in either the primary management of pain or depression.