Med Chem Local Anesthetics

Cocaine: Ester Local Anesthetic: 2 esters, tertiary amine, benzene

Benzocaine: Ester Local Anesthetic: tertiary amine MISSING

aniline --> weak anesthetic PABA derivative

Procaine: Ester Local Anesthetic: aniline, ester spacer, tertiary amine

aniline compared to benzene in cocaine decreases lipophilicity

Procainamide: more stable than procaine... amide compared to ester... metabolized by amidase, N-acetyltransferase, phase II conjugation

Proparacaine: Ester Local Anesthetic: extra propyl, aniline, ester spacer, tertiary amine: longer duration of action... better for hemorrhoids but toxic due to cardiac issue: EYE OINTMENT

Tetracaine: Ester Local Anesthetic: tertiary amine, ester, benzene, secondary nitrogen, 4Cs = tetra.. 2 hours long acting injected intrathecally

Dibucaine: Amide Local Anesthetic: tertiary amine, benzamide, quinoline = pyridine + benzene.. very long half life chemically stable, very lipophilic, too toxic for injection... NOT for DENTAL WORK

Lidocaine: Amide Local Anesthetic: Class 1B anti-arrythmic: less stable shorter acting N closer to aromatic ring... tertiary amine, anilino type amide : 60 minutes

Mepivacaine: Amide Local Anesthetic: similar to lidocaine more lipophilic stays in channel longer.. tertiary nitrogen is piperidine

Bupivacaine: Amide Local Anesthetic more lipophilic than mepivacaine lasts 2-4 hours butyl coming off of piperidine: 2-4 hours

Etidocaine: Amide Local Anesthetic: longer duration than lidocaine 2 3 carbons propyls

Prilocaine: Amide Local Anesthetic: similar to mepivacaine: secondary amine

Pramoxine: Ether Local Anestheic: tertiary amine, ether spacer, benzene... very long acting, used topically 3 weeks max or will accumulate and cause cardiotoxicity

Dyclonine: Ketone Local Anesthetic: tertiary amine as piperidine ring, ketone spacer, benzene... non-irritating, used for sore throat lozenges.. no allergic rxn: injected for infiltration anesthesia