Synthesis of local anesthetics derived from various functional groups
There are analgesics, which, being derived from functional groups other than benzoic acid, aminobenzoic acid or phenylacetamide, also have analgesic properties similar to previously synthesized drugs. The most representative in this group are the following:
Phenacaine, promocaine (pramoxine), bucricaine, ethyl chloride, dimethisoquine, diperodon , ketocaine, myrtecaine, octacaine, dyclonine (diclocaine)
MOb 29 : Dyclonine is an oral anesthetic in Sucrets, one more of the throat lozenges. It is also found in some varieties of Cepacol sore throat spray. Propose the synthesis of the drug. |  |
Retrosynthetic analysis : The structure of ketoamine allows us to propose a disconnection linked to the Mannich reaction (methyl ketone + formaldehyde + secondary amine). Subsequent disconnections of the precursor molecules are related to relatively simple, high-yield chemical reactions.
Synthesis of dyclonine :
MOb 30 : Pramocaine ( also known as pramoxine), is a topical anesthetic used as an antipruritic. Its hydrochloride is soluble in water and therefore more easily absorbed by the skin. Propose a synthesis design for this molecule from simple and affordable materials. |
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Retrosynthetic analysis :
Pramocaine synthesis :
MOb 31: Cyclomethicaine is a local analgesic, propose a synthetic route for this drug. |
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Retrosynthetic analysis:
Synthesis of Cyclomethicaine:
MOb 32. Phenacaine is a local anesthetic. Propose a synthesis plan, for the same. |
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Retrosynthetic analysis: The position of the imino bond suggests that the first disconnection happens through its formation, which originates an imidoyl chloride as precursor molecules. and a nucleophile that turns out to be an aniline derivative. Imidoyl chloride is formed from acetanilide with thionyl chloride and triphenylphosphine in CCl 4
Synthesis of
MOb 33.
Bucricaine, is another local anesthetic, to propose a synthesis design for this drug, starting from simple and affordable materials. |
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Retrosynthetic analysis :
Bucricaine synthesis :
MOb. 34 Diperodon , is a local anesthetic, propose a plan for its synthesis. |
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Retrosynthetic analysis :
Diperodon synthesis :
MOb 35 . Ketocaine , is a local anesthetic, propose a plan for its synthesis. |
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Retrosynthetic analysis:
Ketocaine synthesis:
MOb 36 . Mirtecaine is a local anesthetic used in veterinary medicine. Propose a design for its synthesis. |
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Retrosynthetic analysis:
Synthesis of mirtecaine
MOb 37. Quinisocaine, also called dimethisoquine, is a local anesthetic. Propose a synthesis plan for it, from simple and affordable materials. |
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Retrosynthetic analysis:
Synthesis of quinisocaine:
