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Book Review Klinik und Therapie der Vergiftungen. (Clinical treatment and therapy of poisoning) by S. Moeschlin

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The reaction of allylamines with dichlorocarbene has been
studied by W. E. Parharn and J . R . Potoski. Dichlorocarbene
is produced from potassium t-butoxide/chloroform method
(I), n-butyl-lithium/carbon tetrachloride method (11), and
ethyl trichloroacetate/sodium methoxide method (HI). The
e€i3
R-N-CH~-CH=C<
At
CH3
together with an amide (5) (yield 7 %; ng = 1.4680), the
formation of which can be explained by Stevens rearrangement of the ylide (2). This rearrangement is more important
( I u ) , H = CH3, I t ’ = CGH,
(Ib), R = R‘= C,H,
( l c ) , R = R’= C2H,
allylamines, e.g. ( l a ) , unlike the analogous allyl sulfides,
give the dichlorocyclopropane derivatives, the yield of which
increases with decreasing basicity of the amine. For ( l a ) the
yields obtained by methods I, 11, and I11 are 28 %, 26 %, and
18 %, while for ( l b ) , methods I and I1 give yields of 45 %
and 73 %. When ( l c ) is used as the starting material, the
reaction leads to the dichlorocyclopropane derivative ( 5 %)
in the reactions of the allyl sulfides, since the sulfur ylide is
resonance-stabilized owing to the participation of the d
e e
orbitals of sulfur: Rz-S-CC
istry 32, 275 (1967) / -WG.
t-f
R?;S=C(. / J. org. Chem[Rd 703a IE]
BOOK REVIEWS
For each substance the use, the acute and chronic poisaning
symptoms4(with many of the author’s own cases), and the
methods of identifying the substance in poisoning cases are
described briefly, and in most cases numemus suggested
treatments are added.
In the past 15 years, “Moeschlin” has become a “Bible’
to many clinicians dealing with cases of poisoning, although
this faith is not always justified.
It is generally known nowadays that benzene is a dangerous
hemotoxin and that toluene and xylene are not, since alkylbenzenes are rapidly detoxicated by side-chain oxidation.
However, Moeschlin states on p. 351 : “It was formerly
thought, mainly on the basis of animal experiments, that
toluene and xylene are relatively safe for humans.. . . However, from various observations on similar chronic poisoning
phenomena in persons working with pure toluene or xylene
and from positive animal experiments, today it must be
concluded that toluene and xylene are substantially equivalent to benzene in their toxic action”. The “recent” literature
data included were published in 1929, 1933, 1939, and 1942.
Moreover, the author cannot quote a single case of blood
damage in humans as a result of working with pure toluene
and xylene. It is only too well known that toluene and xylene
were formerly often contaminated with benzene. However,
according to Moeschlin, “only the quantity of these methylated benzenes absorbed is generally rather smaller, owing to
their higher boiling point”. Chemists will have their own
ideas about the hypothesis presented on p. 352, with a
structural formula, according to which benzene acts by
direct addition to cysteine (via an -S- bond), so leading to a
marked cysteine deficiency and a secondary cytochrome
deficiency
Under Benzene derivatives” (p. 371), the book surprisingly
includes naphthalene, naphthol, thymol, and phenolphthalein, which are reported to cause hemolysis and methemoglobin formation, “like aniline and nitrobenzene”. Under
nitrobenzene (p. 387) and aniline (p. 399), it is not pointed
out that rnethemoglobin formation is promoted by alcohol.
In a case of acute dinitrobenzene poisoning (p. 392), on the
other hand, one glass of beer six weeks later is reported to
cause a relapse. The author’s explanation is that the dinitrobenzene “was stored in adipose tissue, and can be remobilized
by fat-soluble agents (alcohol)”. (The alcohol concentration
in the blood after a glass of beer cannot be much more than
0.03 %).
It is of less concern to the reader of this journal that too
little space is given to general treatments and too much to
antidotes. The chemist is more interested in whether the book
will provide him with information about substances that are
injurious to health and about the prevention of poisoning by
potentially dangerous chemicals. Unfortunately, the first
edition contained incorrect information which had been taken
directly from compilations by uncritical authors (particularly
in connection with occupational diseases), and this information has been included unchanged in subsequent editions.
It is impossible in a short review to mention the numerous
errors, incorrect chemical data, and doubtful treatments
contained in the book, and only a few examples will be given
here:
According to Moeschlin, the narcotic Halothan@ (= fluothane) which can allegedly cause acute yellow dystrophy of
the liver, can no longer be used as an anesthetic (p. 338).
Substances such as or,@-dichlorodiethylether and even
ethylene chlorohydrin (p. 344), “should no longer be used in
industry in any circumstances”. Such statements are somewhat too strong. Moeschlin should have protested against
the use of benzene and carbon tetrachloride as solvents in
the home. Substances such as carbon tetrachloride and
methyl bromide are prohibited from use in fire extinguishers
(in Germany at least), though Moeschlin repeatedly states
that they (and even methyl chloride) are used in iire extinguishers, and does not object; he should have demanded
a ban in this case.
Klinik und Therapie der Vergiftungen. (Clinical treatment and
therapy of poisoning) by S. Moeschlin. Georg Thieme
Verlag, Stuttgart 1964. 4th revised and enlarged Edit.,
750 pp., 99 figures. Reprinted unchanged 1965; cloth,
DM 66.-.
In 1951, Moeschlin wrote the first German-language reference
book on poisoning for clinicians. According to the preface,
the reason for writing the book was the “occurrence of a very
large number of new poisons in industry and in the pharmacopoeia”. In the second and third additions, the author
“included many drugs in response to numerous requests by
colleagues”, and the fourth edition, published in 1964,
included a “Section on plastic substances”.
According to the preface, “the arrangement into groups of
poisons follows practical rather than strictly chemical
principles” : After general discussions on poisoning, the
fundamentals of the therapy of poisoning,etc.,some 200 pages
are devoted to “Poisoning by inorganic substances”, and
the next 305 pages to “Poisoning by organic compounds”,
including analgesics and antipyretics, as well as “Plastics
and resins”, soporifics, insecticides, the “principal chemical
warfare agents”, and vitamins and hormones. This is followed
by 60 pages on “Plant poisons and their derivatives”, 35
pages on “Analeptics”, “Antihistamines”, and “Antibiotics”, and finally about 50 pages on toadstool poisons
and animal venoms. The book closes with a list of “Guiding
symptoms in cases of poisoning” (40 pages) and a 34-page
subject index.
644
Angew. Chem. internat. Edit. i Vol. 6 (1967) 1 No. 7
In the bizarre treatment of “Smog” (pp. 374-277), “18 very
toxic nitroolefins” in Los Angeles are confused with the
carcinogenic hydrocarbons. Here the author (p. 355) claims
that “about 300 to 500 new chemical substances are released
for general use every year; in the production of these many
by-products are formed, the major part of which passes into
the atmosphere”.
The new short section on “Plastics and resins” (p. 455) is full
of errors. s-Caprolactam is reported to have a sensitizing
action, and the “danger of sensitization is greatest during the
manufacture of plastics, and less during use of the finished
commercial products”.
According to the book, in one place “toluene diisocyanate is
not a highly toxic substance”, whereas, e.g., it is correctly
stated o n p. 458 that “isocyanates, e.g. Desmodur@, are
highly toxic substances, the inhalation of which leads to
necrosis of the mucous membranes and possibly to fatal
bronchioli tis”.
A most surprising section is that o n p. 457 dealing with the
“Toxic effects of inhalation of liquid particles of plastic into
the lungs”. With reference to the alleged cases of thesaurosis
(= storing-up) due to hair sprays containing polyvinylpyrrolidone (Bergmann 1958), MoeschZin states: “The inhaled
particles solidify in the alveoli of the lungs to form solid
particles of plastic, which can only be partly eliminated in
the sputum” (polyvinylpyrrolidone is water-soluble). MoeschZin is evidently unaware of the fact that most of these “cases”
were incorrectly diagnosed (Boeck’s morbus). On the
contrary, he concludes that “hair sprays containing liquid
plastics should be prohibited”. (In fact, some of the so-called
“cases of thesaurosis” were due to allergic reactions to
shellac, i.e. a natural resin in the hair spray !).
Methyl violet in indelible pencils is claimed to have “a
strong toxic action on tissue, owing to its alkaline reaction”.
The “immediate excision of the injured part” (e.g. of the
hand) suggested by Moeschlin has long been recognised as
foolish. On p. 403 the author refers to the “frequent production of keratitis and conjunctivitis by numerous aniline
dyes” (references from 1905 and-1906!).
Though any number of such errors could be quoted, the
positive points should also be mentioned. An excellent
reference list is given at the end of each chapter and, since
the various authors are named in the text, the physician
can at least check the often doubtful statements about cases
of poisoning. Thus the book could be useful if read very
critically. In a future edition, the entire contents should be
critically sifted and brought up to date by the inclusion of
the latest literature, particularly on industrial toxicology.
The author should preferably enlist the aid of a toxicologist
who is familiar with chemistry, in order that the deserving
work put into the book over the past 15 years may finally
enable the clinician, with the aid of this bible, to diagnose,
H . Oeftel
[NB 564 IE]
assess, and treat poisoning.
Advances in High Pressure Research, Vol. 1. Edited by R . S.
Bradley, Academic Press, London-New York 1966. 1st
Edit., x, 396 pp.. numerous figures and tables, 100 s.
Up to 1952, Bridgman’s classic “The Physics of High Pressure” was practically the only monograph on basic high pressure research. Since 1960, however, at least twenty specialized
works on high pressure have been published, and a series
entitled “Advances in High Pressure Research” has now been
started. The editor has already been very successful with a
two-volume monograph o n “High Pressure Physics and
Chemistry” published in 1963 by the same publishers. Since
high pressure research is mainly defined by the application
of certain experimental techniques, contributions from very
diverse fields will be expected in such a progress report. This
is found even in the first volume, which contains six chapters
of some seventy pages each. The authors of these chapters
have become well known through their own work in the
fields that they describe.
Angew. Chem. internat. Edit. / Vol. 6 (1967) / No. 7
In the first section (“Construction and operation of ultrahigh
pressure equipment”), J . Lees describes the construction and
operation of the “tetrahedral arrangements”; the production and calibration of high pressures is critically discussed.
In the second article, S . D . Hamann describes the effects of
intense shock waves. A particularly interesting part of this
article is the section on the possibility of achieving pressures
of millions of atmospheres with the aid of reflected and converging shock waves. In connection with the article by E.
Whalley o n the refractive and the dielectric properties of
solids and Iiquids under pressure, special mention should be
made of the discussion of the modifications of ice. R. C .
Newton describes the state and future of geophysical research
with high static pressures. Even the outsider will find the
detailed description of the present knewledge .of the earth‘s
crust, mantle, and core interesting. “The stability of solids
under pressure” is discussed by M . Tusi and A . Arai. Special
mention should be made of the section on the transition from
the nonmetallic to Phe metallic state. The last article, by L . S .
Whatlay and A . ,van Valkenburg, is on high pressure optics.
It is mainly confined to the description OF the elegant and
versatile diamond piston arrangement jointly developcd by
the authors in the Bureau of Standards for high pressure
experiments on a microscopic scale.
The volume can be recommended both to those who are experimenting with high pressures and to those who are interested in recent information o n highly compacted matter.
[NB 591 IE]
E. U.Franck
The Peptides. Vol. I. By E. Schroder and K . Liibke. Translated from the German by E. Gross. Academic Press, Inc..
New York-London. Methods of Peptide Synthesis. 1st
Edit. 1965, xvii, 481 pages, several figures, 8 20.00.
All chemists interested in the synthesis of peptides will
certainly welcome the publication of this book. The authors,
who are known t o all experts in this field by virtue of their
numerous publications, work in the main laboratory of
ScheringAG.,Berlin.It isthereforeonlynaturalthat thepresent
volume is intended for the preparative chemist.The references,
which are 2719 in number and cover the literature from 1950
to the end of 1964, permit a rapid and almost complete
assessment of the methods available to date for the synthesis
of peptides.
After a comprehensive discussion of the various protective
groups and the methods of coupling peptide bonds, a
detailed treatment is given of the behavior of individual
amino acids - including some of the rarer ones - in preparative chemistry. The tabular presentation of the most important derivatives of amino acids containing side-chain functional groups deserves special mention.
Shorter sections are devoted to the synthesis of cyclic
peptides, depsipeptides, and peptoids. The plastein reaction,
solid-phase peptide synthesis, and the problem of racemization are also discussed. A most significant part of the book,
155 pages, contains a bibliography and a n i n e x . The
occasional misprint in these ections is something that can
hardly be avoided. On the other hand, t h e failure of the
authors to adopt the nomenclatlfre recommended by the
European Peptide Symposium in 1962 is rather surprising.
Up-to-date tables of synthesized peptides, such as those that
Greenstein and Winitz were able to include in their “Chemistry of the Amino Acids” in 1961, can no longer be expected ;
such a n inclusion would render the book unwieldy. In
accord with the subtitle of this first volume, n o problems such as desalting, purification, and analysis - are touched
upon which are not directly concerned with the synthesis
of peptides.
Printing and presentation of the book are excellent. The
volume will, without doubt, soon be found in every peptide
and protein laboratory, where it will fill a long-standing gap.
645
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