Chemical Synthesis
Epinephrine may be synthesized by the reaction of catechol (1) with chloroacetyl chloride (2), followed by the reaction with methylamine to give the ketone (4), which is reduced to the desired hydroxy compound (5). The racemic mixture may be separated using tartaric acid.
For isolation from the adrenal glands tissue of livestock:
- J. Takamine, J. Soc. Chem. Ind., 20, 746 (1901).
- J. B. Aldrich, Am. J. Physiol., 5, 457 (1901).
Synthetic production:
- A. F. Stolz, Chem. Ber., 37, 4149 (1904).
- K. R. Payne, Ind. Chem. Chem. Manuf., 37, 523 (1961).
- H. Loewe, Arzneimittel-Forsch., 4, 583 (1954).
- Farbenwerke Meister Lucins & Bruning in Hochst a.M., DE 152814 (1903).
- Farbenwerke Meister Lucins & Bruning in Hochst a.M., DE 157300 (1903).
- Farbenwerke Meister Lucins & Bruning in Hochst a.M., DE 222451 (1908).
- Tullar, B. F. (1948). "The resolution of dl-arterenol". Journal of the American Chemical Society 70 (6): 2067. doi:10.1021/ja01186a024. PMID 18863798. edit
- D. Flacher, Z. Physiol. Chem., 58, 189 (1908).
Read more about this topic: Epinephrine
Famous quotes containing the words chemical and/or synthesis:
“If Thought is capable of being classed with Electricity, or Will with chemical affinity, as a mode of motion, it seems necessary to fall at once under the second law of thermodynamics as one of the energies which most easily degrades itself, and, if not carefully guarded, returns bodily to the cheaper form called Heat. Of all possible theories, this is likely to prove the most fatal to Professors of History.”
—Henry Brooks Adams (1838–1918)
“The spider-mind acquires a faculty of memory, and, with it, a singular skill of analysis and synthesis, taking apart and putting together in different relations the meshes of its trap. Man had in the beginning no power of analysis or synthesis approaching that of the spider, or even of the honey-bee; but he had acute sensibility to the higher forces.”
—Henry Brooks Adams (1838–1918)