Editing Enantioselective synthesis (section)

====Thalidomide====
While it was known that the different enantiomers of a drug could have different activities, with significant early work being done by [[Arthur Robertson Cushny]],<ref>{{cite journal|last=Cushny|first=AR|title=Atropine and the hyoscyamines-a study of the action of optical isomers|journal=The Journal of Physiology|date=2 November 1903|volume=30|issue=2|pages=176–94|pmid=16992694|pmc=1540678|doi=10.1113/jphysiol.1903.sp000988}}</ref><ref>{{cite journal|last=Cushny|first=AR|author2=Peebles, AR|title=The action of optical isomers: II. Hyoscines|journal=The Journal of Physiology|date=13 July 1905|volume=32|issue=5–6|pages=501–10|pmid=16992790|pmc=1465734|doi=10.1113/jphysiol.1905.sp001097}}</ref> this was not accounted for in early drug design and testing. However, following the [[thalidomide]] disaster the development and licensing of drugs changed dramatically.

First synthesized in 1953, thalidomide was widely prescribed for morning sickness from 1957 to 1962, but was soon found to be seriously [[teratogenic]],<ref>{{cite journal|last=McBride|first=W. G.| title=Thalidomide and Congenital Abnormalities |journal=The Lancet|year=1961|volume=278|issue=7216|pages=1358|doi=10.1016/S0140-6736(61)90927-8}}</ref> eventually causing birth defects in more than 10,000 babies. The disaster prompted many countries to introduce tougher rules for the testing and licensing of drugs, such as the [[Kefauver-Harris Amendment]] (US) and [[Directive 65/65/EEC1]] (EU).

Early research into the teratogenic mechanism, using mice, suggested that one enantiomer of thalidomide was teratogenic while the other possessed all the therapeutic activity. This theory was later shown to be incorrect and has now been superseded by a body of research.<ref>{{cite journal |last1=Ito |first1=Takumi |last2=Ando |first2=Hideki |last3=Handa |first3=Hiroshi |title=Teratogenic effects of thalidomide: molecular mechanisms |journal=Cellular and Molecular Life Sciences |date=May 2011 |volume=68 |issue=9 |pages=1569–1579 |doi=10.1007/s00018-010-0619-9|pmid=21207098 |s2cid=12391084 |pmc=11114848 }}</ref> However it raised the importance of chirality in drug design, leading to increased research into enantioselective synthesis.