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Malignant hypertension is defined as extremely elevated blood pressure (BP) with or without target organ damage. It can be either hypertensive urgency, characterized as malignant hypertension without any clear evidence of immediate organ damage, or hypertensive emergency with proof of new or worsening target-organ damage. The modern definition of hypertensive emergencies without retinopathy would be based on the presence of acutely raised BP with injury to at least three target organs. Pheochromocytoma is the rarest cause of malignant arterial hypertension, characterized by the classic triad of headache, sweating, and palpitations. It is rare in adolescents, and it often presents a unique surgical challenge due to catecholamine secretion. Laparoscopic adrenalectomy is the recommended surgical treatment of choice. Although it is a common procedure performed in adults, it has not yet been reported in adolescents in the Caribbean. This case report details the presentation of a 16-year-old boy from Trinidad and Tobago, who had a six-month history of episodic headaches, sweating, palpitations, blurry vision, and significantly elevated BP (up to 225/120 mmHg). His clinical picture was further complicated by new-onset diabetes mellitus and a family history of hypertension and diabetes on both maternal and paternal sides. Investigations revealed significantly elevated catecholamine levels, and imaging confirmed a right adrenal mass consistent with a pheochromocytoma. This case highlights both the clinical complexity and the feasibility of performing laparoscopic adrenalectomy in adolescent patients within a Caribbean healthcare setting.