Chemical Aspects of Local and Regional Anesthesia

Ostercamp, Daryl L.; Brunsvold, Robert

doi:10.1021/ed083p1816

Cited by 2 publications

(2 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Local anesthetics, which reversibly block nerve impulses, can be divided into two main groups, esters (e.g., cocaine, benzocaine, procaine, tetracaine) and amides (e.g., lidocaine, prilocaine, bupivacaine), by the functional group that connects the hydrophobic group (generally an aromatic ring) and the hydrophilic group (frequently a secondary or tertiary amine group). 4 Side effects of local anesthetics are common; a metabolite of benzocaine is p-amino benzoic acid, which is associated with allergic reactions, and a breakdown product of prilocaine, o-toluidine, can produce methemoglobinemia. Also, prilocaine has been reported to induce apoptosis in osteoblastic cells.…”

Section: ' Project Descriptionmentioning

confidence: 99%

“…The multistep divergent synthesis of two local anesthetics, prilocaine hydrochloride ( 5 ) and benzocaine ( 8 ), with a common initial three-step reaction sequence starting from toluene is described as an example project (Scheme ). Local anesthetics, which reversibly block nerve impulses, can be divided into two main groups, esters (e.g., cocaine, benzocaine, procaine, tetracaine) and amides (e.g., lidocaine, prilocaine, bupivacaine), by the functional group that connects the hydrophobic group (generally an aromatic ring) and the hydrophilic group (frequently a secondary or tertiary amine group) . Side effects of local anesthetics are common; a metabolite of benzocaine is p -amino benzoic acid, which is associated with allergic reactions, and a breakdown product of prilocaine, o -toluidine, can produce methemoglobinemia.…”

Section: Project Descriptionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course

Demare

Regla

2011

J. Chem. Educ.

View full text Add to dashboard Cite

ercito de Oriente, 09230 M exico, D.F., M exico b S Supporting InformationO ur academic approach is based on the premise that learning is facilitated in a research environment, which involves independent study, decision making, and problem solving through research projects. 1À3 To this end, a nontraditional advanced undergraduate organic chemistry laboratory course was developed. The project-oriented system consists of halfsemester research projects (about eight 4-h lab sessions) that involve the multistep synthesis of a variety of classical pharmaceutical drugs, with methodologies usually adapted from primary literature. One of these projects is described; the multistep synthesis of two local anesthetic drugs, benzocaine and prilocaine, from a common three-step sequence starting from toluene that requires the student to formulate a hypothesis and to design experiments to test it. ' LABORATORY DYNAMICSStudents work singly or in pairs, with different projects. Each instructor is in charge of up to 10 students. The semester work starts with three to five simple experiments, presented in a nonconventional laboratory manual (more accurately, a laboratory guide) that includes: (i) an introduction describing the work system; (ii) 40 experimental proposals (each featuring a reaction scheme, main objective, procedure references, a study guide, prelab questions, and notes, as well as IR and NMR spectra); and (iii) 10 appendixes addressing topics such as the lab notebook, experimental design, microscale, waste disposal, bibliographic research, and laboratory rules (the original version of this manual, in Spanish, is included in the Supporting Information).Before conducting each experiment, students search for information, discuss it with the instructor, and outline a laboratory work plan, generating a grade that will be averaged with the lab work and report. In this preliminary evaluation, the instructor inquires about the theoretical background of the experiment (reaction type, mechanism, stoichiometry, etc.) and the procedure, frequently advising students against the idea that they must "follow instructions step-by-step" to achieve success. This interaction is intended to promote a critical process that allows students to design their own work plan and gives them selfconfidence. The dialogue between the students and instructor may be time-consuming, but the instructors must be aware of the work the students are carrying out, making sure that the students know, before initiating each step, how they are going to do it, why, and what to expect.At the beginning of the course, pharmaceuticals are assigned to the students, who do a time-constrained bibliographic search in Chemical Abstracts (CA), either in printed form or through the SciFinder database, seeking information on syntheses for the assigned drug. This search (typically 1950 through 1980) frequently renders several nonrecoverable papers or patents, so it is sometimes necessary to discuss alternatives, and then plan the project and design experimental work based o...

show abstract

Section: ' Project Descriptionmentioning

confidence: 99%

Section: Project Descriptionmentioning

confidence: 99%