Ch_322b_19.10 - pharmacologically useful a number of...

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The Barbiturates An important class of drugs called the barbiturates are synthesized in a double condensation reaction with diethyl malonate and urea. The parent compound is barbituric acid , which was first synthesized in 1864 by Adolph von Baeyer when he was a young student of August Kekule'. Baeyer went on to a very distinguished career in organic chemistry (Nobel Prize in Chemistry, 1905). The origin of the name is alleged to come from von Baeyer who, at the time of his discovery, was in love with a girl named Barbara . H 2 C COEt O = COEt O + C=O H 2 N : H 2 N urea NaOEt/110 o C (-2 EtOH) H 2 C C-N C-N O O C=O H H barbituric acid (K a ~ 10 -4 )
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The Barbiturates as Drugs The medicinal value of the barbiturates was discovered in 1903 by Joseph von Mering. Although barbituric acid itself is not
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Unformatted text preview: pharmacologically useful, a number of derivatives prepared by introducing R and R' groups into the diethyl malonate are used as drugs. Doses of these barbiturates of 100 mg often will induce sleep. A lethal dose for an average size human is about 1500 mg. In combination with ethyl alcohol, barbiturates are extremely dangerous producing a dramatic depressant effect on humans that can cause death. Barbiturates also are addictive. N O N O = C 2 H 5 C 6 H 5 N O N O CH 2 =CHCH 2 CH 3 CH 2 CH 2 CH CH 3 barbital induces sleep in dogs phenobarbital sedative for humans, used as anti-convulsant in treatment of epilepsy secobarbital (seconal) a sedative H H H H O O N O N O C 2 H 5 C 2 H 5 H H O...
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This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.

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Ch_322b_19.10 - pharmacologically useful a number of...

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