Up to 40% of patients taking clonidine (Catapres) will experience dry mouth and about a third will have drowsiness, headache, and sleepiness. Other common side effects include constipation, dizziness, and local skin reactions with use of the Catapres-TTS skin patch. Reserpine use is linked with possible side effects including nightmares, stuffy nose, depression, and an inability to fall asleep. Diarrhea and heartburn are also possible. Guanadrel and guanethidine can cause diarrhea and other gastrointestinal issues – as well as dizziness and drowsiness.
As for when to check your blood pressure, the most important thing is to do it consistently the same time of the day (ask the doctor which time he prefers and also what time in relation to taking your medication). The following article has a lot of good information for someone just starting to monitor their blood pressure: https://www.drugs.com/cg/how-to-take-a-blood-pressure.html
Hypertension clinical guidelines from the American Heart Association are comprehensive guidelines for healthcare professionals for the detection and treatment of high blood pressure in a wide range of patients. Included in the 2018 hypertension clinical guidelines are proper methods for measuring blood pressure, risk factors for hypertension, and hypertension treatment for different populations.

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Unlike high blood pressure symptoms, which are poorly defined and often totally absent, low blood pressure symptoms tend to be more upfront and easily recognizable. The development of symptoms is often a warning sign of a potentially serious underlying disorder. Generally speaking, your blood pressure would need to fall pretty dramatically before symptoms develop.
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