Because I'm the most linguistically and grammatically oriented member of my family, I have become the family etymologist. A few weeks ago, Jayna casually pondered to me the following etymology question:

Is the word "proctor," the man who watches everyone during tests, related to the word "proctology?"

To answer this, I quickly went to my Greek and Latin dictionaries. The easiest thing to do was to check out my Latin dictionary, Chambers Murray, to see if there was anything close. The word prōcūrātor is defined as "one who is in charge," "an administrator, manager." Thus, a proctor is the administrator of a test.

The second half of "proctology" comes from the Greek λόγος (logos), so I looked up the prokt- words in Greek. It turns out Liddell and Scott define πρωκτός (prōktos) as "anus." The search ends there.

In other words, no they are not related. That is, unless you have a rather strict proctor, one whom you would consider a pain in the πρωκτός region.