Pyrrocaine
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| Preferred IUPAC name N-(2,6-Dimethylphenyl)-2-(pyrrolidin-1-yl)acetamide | |
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| Properties | |
| C14H20N2O | |
| Molar mass | 232.327 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Pyrrocaine is a local anesthetic drug. The cogency of pyrrocaine is equivalent to lidocaine in blocking the motor nerve and sensory. Pyrrocaine was proven to be somewhat harmless compared to lidocaine. No signs of methemoglobinemia was found while observing. It was considered unsafe for acute porphyria treatment. No evidence is found that it is profitly used now.[1]
History
[edit]In the 1960s it was most of the time used as a nerve blocker dental anesthetic and dentists recommended it due to its fast commencement.[1]
Adverse effects
[edit]Pyrrocane has very similar side effects on blood pressure and heart rate compared to lidocaine.[2]
Synthesis
[edit]Selfsame as lidocaine, albeit interposing pyrrolidine for diethylamine.
Amide formation between 2,6-Dimethylaniline (1) and Chloroacetyl chloride (2) gives [1131-01-7] (3). Displacement of the remaining halogen by pyrrolidine (4) completed the synthesis of Pyrrocaine (5).
See also
[edit]References
[edit]- ^ a b "NCATS Inxight: Drugs". drugs.ncats.io. Retrieved 2018-08-07.
- ^ Annals of Dentistry. New York Academy of Dentistry. 1983.
- ^ Löfgren, Nils; Tegnér, Claës; Takman, Bertil (1957). "Studies on Local Anesthetics. XVI.". Acta Chemica Scandinavica 11: 1724–1737. doi:10.3891/acta.chem.scand.11-1724.
- ^ US 2813861, Schlesinger, Albert & Gordon, Samuel M., "Pyrrolidino-2, 6-dimethyl anilide salt of 8-[2'-methoxy-3'-(7-theophyllinyl mercuri)] propyl-coumarin-3-carboxylic acid", published 1957-11-19, assigned to Endo Laboratories, Inc.
- ^ GB 986993, "Local anesthetics", published 1965-03-24, assigned to Graham Chemical Corp.