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And my mentor, a real poineer of nursing, taught me that if I just lifted the tip of the patient's nose a little bit, it made the NG catheter tip slip past the sinus and into the nasopharynx a little easier. It wasn't completely without discomfort, but there was a definite difference.
Slipping a NG tube down an unconscious patient has a lot of risks- the biggest one is trauma to the larynx and bronchi due to going down the wrong tube. The best way to do it is with the patient wide awake, sitting bolt upright, and swallowing a glass of ice water as the tube is advanced to keep the epiglottis closed over the trachea.