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Hi. Welcome to Just Answer. My name is***** and I've been a veterinarian for 15 years. Diphenhydramine is used in veterinary medicine for its antihistamine properties when dealing with itching / allergy situations. It doesn't really have any reliable / significant sedation or relaxation affects on most dogs. For a dog that is already anxious about nail trims, I wouldn't feel that it being given orally prior to that event would provide much help. What would be better here is trying to acclimate her to the nail trim. Basically this is where the nail trimming is made more of a positive event. Switching nail trimmers can be done if she's learned that she doesn't like the others. It is best to do the nail trimming after she's had some good exercise - play time or a long walk - so she'll have used up her energy and be more ready to be relaxed / rested. Giving her small treats as she's getting them done can help to make it more positive. Trying to do just one or two paws at a time and then progressively doing all of them. Initially having help to assist with the process is good too as one person can be solely in charge of talking to her and helping her to realize that the process isn't a bad one while the other person does the trim. Overall slow and steady positive reinforcement can make the process one that is much better tolerated. The use again of the Benadryl is something that most likely won't help the process as it doesn't really relax / sedate them. Some owners may ask their vets for an oral sedative like acepromazine to use initially as this may provide much more reliable calming / sedation when the nail trims are being first started up. I feel that a slow and steady approach though usually has pretty good success.
One approach that I've had some owners do is to actually just trim one nail a day. This can make the process a very short one for that day where with positive reinforcement and treats, the trimming of the one nail is over before they know it and they start to feel that it isn't that bad of a process.