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ester- benzoic ambucaine [1] diester - aminosalicylic articaine: Astracaine, Septanest, Septocaine, Ultracaine, Zorcaine Amide benzocaine: Anbesol, Orajel Ester - Aminobenzoic Short benzonatate: Tessalon bupivacaine: Marcaine, Sensorcaine, Vivacaine 1957 (Ekenstam) 1963 (Widman and Telivuo) Amide Moderate butacaine: ester- aminobenzoic ...
Many local anesthetics fall into two general chemical classes, amino esters (top) and amino amides (bottom). A local anesthetic (LA) is a medication that causes absence of all sensation (including pain) in a specific body part without loss of consciousness, [1] providing local anesthesia, as opposed to a general anesthetic, which eliminates all sensation in the entire body and causes ...
According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC. [ 1 ] An example of an ester formation is the substitution reaction between a carboxylic acid ( R−C(=O)−OH ) and an alcohol (R'OH), forming an ester ( R−C(=O)−O−R' ), where R and R′ are ...
Structurally, amino esters consist of three molecular components: a lipophilic part (ester); an intermediate aliphatic chain; a hydrophilic part (amine); The chemical linkage between the lipophilic part and the intermediate chain can be of the amide-type or the ester-type, and is the general basis for the current classification of local anesthetics.
The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water.
The carbonyl oxygen in esters is weakly basic, less so than the carbonyl oxygen in amides due to resonance donation of an electron pair from nitrogen in amides, but forms adducts. As for aldehydes , the hydrogen atoms on the carbon adjacent ("α to") the carboxyl group in esters are sufficiently acidic to undergo deprotonation, which in turn ...
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Esters exhibit less resonance stabilization than amides, so the formation of a tetrahedral intermediate and subsequent loss of resonance is not as energetically unfavorable. Anhydrides experience even weaker resonance stabilization, since the resonance is split between two carbonyl groups, and are more reactive than esters and amides.