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He is now in a nursing home and gets his medication crushed and in syrup. Often he holds his medicine in his mouth until the nurse is gone and then spits it out. He can hold this for an hour or more and then still spit it out. There is no reasoning, no coaxing, no tickling his throat. Nothing seems to work.

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He is losing the ability to swallow. Lukewarm liquids are less likely to trigger a swallowing reflex, but sensibly warm things or sensibly cool things seem to go better. Try some ice cream, the cold triggers a swallowing effort. Or if he likes a hot cocoa, use that.
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There is this formula called Thick-it that helps a ton, to put in various liquids.
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