Phenothiazine is a privileged bioactive scaffold, made up of a tricyclic aromatic unit with a thiazine center . It is present in multiple antipsychotic drugs, including promethazine (Phenergan) chlorpromazine (Thorazine), thioridazine (Mellaril), and trifluoperazine (Stelazine), and prochlorperazine (Compro). In addition, the phenothiazine drugs are toxic at high dose and there is no specific antidote for overdoses. CDs that bind phenothiazines well could thus be of interest as antidotes. However, little is known about how even the most straightforward CD derivatives interact with this class of drugs. The present study clearly shows that phenothiazine is also a privileged scaffold for tight-binding CD guests, as every guest studied here shows good affinity for native βCD and two derivatives thereof. Intriguingly, though, none of these drugs bound a derivative permethylated at the 3 position. Notable additional observations include: