Tooth extraction

Tooth extraction, or pulling teeth, was the process of removing a tooth from an individual's jaw. It was usually performed by dentists, although in Earth's Ancient West, barbers traditionally pulled teeth, a practice that carried over to the Skagaran colony following the abduction of Humans in the 19th century. (ENT: "North Star")

In 2153, MacReady offered Jonathan Archer some Skagaran whiskey, explaining that although the alcoholic beverage was illegal, he let Henry keep some around for pulling teeth (presumably to dull the pain). (ENT: "North Star")

The Cardassian Bureau of Identification extracted a first molar from every Cardassian, usually at the age of ten. Prisoners of the Cardassian Union also underwent this procedure, including Miles O'Brien upon his arrest in 2370, an experience he described as unpleasant. Odo, upon being threatened with a contempt of court charge during O'Brien's trial, expressed his "regret" that he had no teeth to give the Bureau. Later, a Cardassian using the alias of Raymond Boone was uncovered after an examination by Julian Bashir revealed that he too was missing a first molar. (DS9: "Tribunal")

Any particularly difficult task could be compared to pulling teeth. In 2373, following Rom's being taken into custody on Deep Space 9, Odo commented on the difficulty of his interrogation of the Ferengi, saying that "For the first forty minutes, it was like pulling teeth even getting him to admit his name." (DS9: "The Assignment")