Studies on the duration of local anaesthesia: structure/activity relationships in a series of homologous local anaesthetics.
When the number of carbon atoms on the piperidine-nitrogen of the mepivacaine molecule was increased up to four or five carbons, the toxicity of the compounds and the duration of their local anaesthetic effects were increased. With longer N-alkyl-chains, the general toxicity and the local anaesthetic potency - but not the tissue toxicity - were reduced. In dental infiltration anaesthesia only the short-chain compounds offered an acceptable local anaesthesia. In these tests, the medium-chain compounds had a very unfavourable quotient between dental anaesthesia and soft tissue anaesthesia, while the long-chain compounds could not be tested at all in man because of their tissue irritating properties.
D000328:Adult; D000766:Anesthesia, Dental; D000772:Anesthesia, Local; D000779:Anesthetics, Local / Q000008:administration & dosage / Q000494:pharmacology* / Q000633:toxicity; D000818:Animals; D002045:Bupivacaine / Q000494:pharmacology / Q000633:toxicity; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D005385:Fingers / Q000294:innervation; D006168:Guinea Pigs; D006801:Humans; D007275:Injections, Intravenous; D007279:Injections, Subcutaneous; D007928:Lethal Dose 50; D008297:Male; D008619:Mepivacaine / Q000494:pharmacology / Q000633:toxicity; D051379:Mice; D011817:Rabbits; D012584:Sciatic Nerve / Q000187:drug effects; D013329:Structure-Activity Relationship; D013997:Time Factors
D000779:Anesthetics, Local; D008619:Mepivacaine; D002045:Bupivacaine