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2. Mouth and Teeth ailments:
A. Removing an aching tooth:
A toothache which has made one weak: Based on the laws of the different levels of severity of illnesses listed in Chapter 2, one who has a tooth ache which causes him such pain that his entire body feels sick (is allowed to transgress Shabbos through a gentile) [and] may tell the gentile to remove [the tooth].
The reason it is allowed despite ones assistance that he is giving to the dentist: Now, although the Jew helps him locate the tooth and slightly assists him to take it out, [nevertheless] this does not pose a problem because his help is not meaningful as even if the Jew were to not help him in this assistance [that he is giving] but would also not stop [the gentile from doing his job] then the gentile would be able to do it himself.
A toothache which has not made one weak: (And according to those opinions which say that any action which is not done for its own use is only Rabbinically forbidden then it is permitted to remove [the tooth] through a gentile even if the entire person’s body has not become sick [so long as it is more than a mere ache] as was explained [in Halacha 328/20]) [See Q&A regarding tooth which its majority has begun coming out]
B. Taking medicine:
A minor ache: One who has a toothache may not gargle vinegar and then spit it out being that it is recognizable that he is doing it for healing. [The same applies to taking any medicine, that doing so is forbidden, unless the ache is so strong that he is bedridden due to it as will be explained next.] However, he may gargle and swallow it or dip a piece of bread into it and eat it as is normally done during the week. Even through a gentile it is forbidden to do any [treatment] for him even if there is no resemblance of a forbidden action even Rabbinical, if it is recognizable that [the treatment] is being done for healing.
A major ache: However this only applies by a minor [tooth] ache, however if he is in so much pain that his entire body is weakened because of it, then he is permitted [take medicine and may] do through a gentile [even Biblical prohibitions, and if his entire body is not weakened but he nevertheless feels pain to the point that he is slightly sick then a gentile may nevertheless do for him] anything which is only Rabbinically prohibited, as was explained above.
Removing the tooth: If it hurts to the point that one’s entire body feels weak, then he may ask a gentile to pull it out. According to some even if one’s entire body is not weak from the pain, but is more than a mere ache, then one may ask a gentile to remove it.
Gargling vinegar: If it is a mere ache then one may not even gargle vinegar and the like and then spit it out. Although he may gargle it and swallow it or dip his bread in it and eat it, as then it is not noticeable that he is eating it as medicine. If, however, the pain is so strong that one feels weak in his entire body then all medicine may be taken.
Medicine: Is forbidden unless one is bedridden or weak throughout his entire body.
May one pull out a loose tooth?
If majority of the tooth has already detached and pulling it out will not release blood, then it is allowed to be pulled out if it is causing one pain.
May one wear detachable braces on Shabbos?
See Chapter 2 Halacha 7 Q&A there!
I suffer from dull tooth pain. May I bite on a clove on Shabbos for the sake of relieving it?
You should only do so in the process of eating such as to add cloves to a salad or other food and eat it within that food, however you should not need it plain. If, however, the pain is so strong that you feel weak in your entire body, then you may chew the clove regularly and even take medicine, as is the law of allowance by anyone who is sick.
Explanation: It is forbidden to take medicine on Shabbos even if one is in pain unless one is sick, which is defined as feeling weakness throughout the entire body. This restriction applies even against eating foods for medicinal purposes if it is being done in a way that is evident to all that its purpose is for medicine. However, the restriction does not apply if one consumes the food in the regular way of eating even if its true intent is for medicinal purposes, being that this intent is not apparent to others. Accordingly, we concluded above that while certainly one may eat the clove as part of an ingredient of his food or salad, even if his intent is for medicinal purposes being that there are plenty of healthy people who do so, and it is hence not apparent to others that is being done for medicinal purposes, nonetheless, he should not chew it plain being that, as far as I’m aware, this is not normally done by even a minority of healthy people for eating purposes and will hence be viewed by others as being done for medicinal purposes.
Sources: Admur 328:1 [regarding general medicine prohibition]; Admur 328:38 [regarding the permitted and forbidden ways of treating toothache based on the intensity of the ache and on whether the treatment appears like medicine to others]; Admur 328:43 and Ketzos Hashulchan 134 footnote 16 [regarding if the general prohibition of medicine applies to foods]; See Piskeiy Teshuvos 328:61 footnote 485 that while it is permitted to eat garlic in salad for medicinal purposes, it is not permitted to eat garlic plain for medicinal purposes being that not even a minority of people do so.
C. Chewing medicinal gum and applying toothpaste to one’s teeth:
For medical purposes: One may not chew a species of resin called Mastichi and may not rub a drug on ones teeth when ones intention in doing so is for healing purposes.
To remove bad odor: However, if he is only doing so to [remove bad] odor from his mouth, then it is allowed [to rub an herb or chew the gum].
Summary-Chewing medicinal gum and applying toothpaste to one’s teeth:
One may not do so for medical purposes. However, one may do so in order to remove bad odor from one’s mouth.
May one brush his teeth on Shabbos?
One may place thin creamy toothpaste on his hand and then smear it on his teeth. It is forbidden to place it directly on a toothbrush and then smear it as doing so is a mundane act. Practically the custom is to avoid brushing one’s teeth at all on Shabbos. [See Piskeiy Teshuvos 326/3 for all details]
May one use mouthwash to remove bad odor?
Yes, this is permitted.
May one floss his teeth on Shabbos?
One may floss his teeth so long as he beware not to cause bleeding. Likewise, it is forbidden to cut the piece of floss off on Shabbos due to the prohibition of Tikkun Keli.
 Admur 328:3
 Admur ibid; Mamar Mordechai, brought in M”B 316:30
Other opinions: Some Poskim rule that removing a tooth for medical purposes [or doing any bruise for medical purposes] is considered a Melacha Shetzricha Legufa. [M”A 316:15; 328:3; M”B 316:30]
 Admur 328:38
 As explained in Chapter 2 Halacha 2
 This insert is placed by the Ketzos Hashulchan [Chapter 128 footnote 9]. Without it the statement contradicts what was explained above in Halacha 19. So rules also Mishneh Berurah 328:100.
 Admur 328:3
 Admur 328:38
 Sheivet Halevy 5:39, brought in Piskeiy Teshuvos 328:24
 As this is similar to a nail which has peeled off its majority which ideally may be removed. [Although practically may not due to what will be explained in the Halacha dealing with it.]
 Piskeiy Teshuvos 328:35; SSH”K 34:29
 Admur 318:42
 This is a type of resin with a pleasant smell which comes out of a tree. [Mishneh Berurah 328:114]
 See next Halacha note 31
 Admur 318:42
 Doing so is not a problem of smearing being that the prohibition only applies if one smoothens out the bumps of which there is no concern regarding one’s teeth. However, a thick toothpaste is forbidden due to Nolad as it becomes liquidly when placed in the mouth.
 Ketzos Hashulchan 138 footnote 31
 Piskeiy Teshuvos 328:26 based on 328:42