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Various

"Scientific American Supplement, No. 623, December 10, 1887"

Optical methods of examination have proved of great value,
and are destined to play an important part in such work.
Among the most complex alkaloids are those of the quinine group. As
yet chemists have got no further with these than the oxidation
products; but the study has afforded us several new antipyretics and
many interesting facts. It has been found, for example, that
artificial quinine-like bodies, which fluoresce and give the green
color with chlorine water and ammonia, have antipyretic properties
like quinine, but their secondary effects are so pernicious as to
prevent their use. If, however, such bodies are hydrogenized or
methylated they lose their fluorescing property, do not give the green
color, and their secondary effects are removed. Knowledge of these
facts led to the discovery of thalline. It is prepared from
paraquinanisol, one of the objectionable bodies, by reduction with tin
and hydrochloric acid. The following formulae show the constitutional
relationship of these compounds:
CH CH CH CH_{2}
/ \ / \ / \ / \
(CH_{3}O)C C CH (CH_{3}O)C C CH_{2}
| | | | | |
HC C CH HC C CH_{2}
\ / \ / \ / \ /
CH N CH NH
Paraquinanisol Thalline
C_{9}H_{6}.


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