A review of information on anabasine and nornicotine, 1938-1944

Material Information

A review of information on anabasine and nornicotine, 1938-1944
Roark, R. C ( Ruric Creegan )
United States -- Bureau of Entomology and Plant Quarantine
Place of Publication:
[Washington, D.C.]
U.S. Dept. of Agriculture, Agricultural Research Administration, Bureau of Entomology and Plant Quarantine
Publication Date:
Physical Description:
23 p. : ; 27 cm.


Subjects / Keywords:
Insecticides ( lcsh )
Alkaloids ( lcsh )
Nicotiana ( lcsh )
bibliography ( marcgt )
federal government publication ( marcgt )
non-fiction ( marcgt )


Includes bibliographical references (p. 16-23).
General Note:
Caption title.
General Note:
General Note:
"March 1945."
General Note:
"Supplement to E-537 and E-561."
Statement of Responsibility:
by R.C. Roark.

Record Information

Source Institution:
University of Florida
Rights Management:
This item is a work of the U.S. federal government and not subject to copyright pursuant to 17 U.S.C. §105.
Resource Identifier:
030286926 ( ALEPH )
779540818 ( OCLC )

Full Text
Li. RY

durch 1945 E-636

United States Department of Agriculture
Agricultural Research Administration
Bureau of Entomology and Plant Quarantine


(Supplement to E-537 and E-561)

By R. C. Roark, Division of Insecticide Investigations



Introduction . . * * * *
Chemistry of anabasine . . . nn
Occurrence of anabasine and nornicotine

* S S S 0
* 0 0 0
* 0 5 *~ 0

Anabasigt 0 0 0 0 0 0 a q 0 0
Arab.,is * * * * * * * *
Jicotlana . * . . . . *
Occurrence of nornicotine in commercial nicotine
sulfate 0 a * .* a * 0 *
extraction of anabasine from plants *. . .
Composition of commercial anabasine sulfate made
Anabasis . . . * * *
Analytical methods .
Separation of anabasine from nicotine and other
alkaloids . . * . . .
Pharmacology of anabastne and nornicotine .
Anabasine . * * * * * .
Nornicotine * * * * * * *
Insecticidal value of anabasine . . . *
Thysanoptera . . . * * * *
Homoptera . . .* * * * .
Hemiptera . . . * * * *
Diptena . . * * * * * * *
Coleoptera . . * . . .
Anoplura * . . * . . .
Patents * . . . * . . . *
Literature cited. * . . * *

. 0 3

* 0 S
* 5 0
* 0 0
* p

MAR 21 1945



In April 1941 the Bureau of Entomology and Plant Quarantine issued
E-537, A Review of Information on Anabasine, and in March 1942 B-561, A
Review of Information on Nornicotine. These reviewed 163 and 5a publica-
tions, respectively. The purpose of the present publication is to bring
up to date all available information on both these promising insecticides.

In preparing this review the following abstract journals, published
from 1938 to 1943, inclusive, were searched: Biological Abstracts, Chemi-
cal Abstracts, Chemisohes Zentralblatt, Experiment Station Record, Index
Medicus, and Review of Applied Entomology (Series A and B). In addition
the Quarterly Bibliography on Insecticide Materials of Vegetable Origin
through No. 26 (January to March 1944), issued by the [Great Britain]
Imperial Institute Consultative Committee on"Insecticide Materials of
Vegetable Origin, was consulted.


The following constants for anabasine are given: Boiling point (p =
238 mm.) 280.90 C., freezing point 90, specific rotation -83.10 Its
parachor coincides closely with the theoretical parachor.-- Sokolov (76).

In a report on the reactions of amino-n-methylanabasines the follow-
ing melting points are given:
0 C.

alpha-Amnino-N-methylanabasine 95 95.3
Acetyl ------------ 72 73
Diacetyl, hydrate ------- 60.5- 62.6

alpha'-Amino-N-methylanabasine 91.5- 92.5
Aoety. ----. ------------ 122 122.5
Propionyl -- -- 97 98
Benzoyl -------------- 104 106
Dibenzoyl --------------- 142 143

The picrate of the alpha compound decomposes at 238-239.5, and that of
the alpha' compound at 227.5-228. The boiling point of the diacetyl
derivative is 160-162 (p =4 mm.), and that of propionyl derivative
(p =5.5 mm.) 193-200.--Kabachnik and Xitaer (32).

The dihydrochloride of dichloroanabasine is obtained by passing
chlorine into anabasine in cold alcohol. The yield is 29-63 percent.
It melts at 203*7C (dec.) Free dichloroanabasine dissolves in water
with difficulty, is soluble in ethyl alcohol, slightly less soluble in
ether, and melts et 51-3. It reacts with picric acid, forming a piriate,

-3 -

melting at 91-5. Nicotinic acid is formed by oxidizing dichloroanabaslne
with a permanganate solution. Bromination of anabasine under the same con-
ditions forms bromo-substltuted compounds, melting at 1050 and 1355, which
are very hygroscopic and very unstable. At 80-100 they are decomposed by
water with the separation of anabasine. The amount of bromine decreases con-
siderably on prolonged keeping of the bromo-substltuted compounds. The pic-
rate of one bromo-substltuted compound melts at 199-201, and according to its
bromine content it corresponds to a monobromoanabasine.-- Dashkevlch (20).

The most important sources of anabasine are the tree tobacco, Nicotiana
glauca, a native of Argentina and Uruguay, and the Russian shrub, Anabasis
aphylla, which is related to the American tumbleweed. Although N. glauca
is a native of South America, it is very much at home in Mexico and in the
Southwestern United States.-- Higbee (27).

A review of information on anabasine discusses sources, chemistry,
alkaloids of Anabasis aphylla, physiological action, insecticidal proper-
ties, and commercial forms used for pest control.-- Holman (25, pp. 21-25).

A comprehensive review on the alkaloids of tobacco includes nornicotine
and anabasine.- Jackson (1).


The anabasine content of Anabasis aphylla was found to be inversely
proportional to the degree of moisture. However, this relationship cannot
be accepted as an absolute rule without further verifications.--
Kudryavtsev (3).

Anabasis aphylla contains anabasine, lupinine, aphyllidine, and
aphylline. The preparation of salts and other derivatives is described.
Anabaslne, upon reacting with boiling 5-percent hydrochloric acid, under-
goes ring opening.- Spath, Galinovsky, and Mayer (52).

In a study of saline plants of Turkmania Anabasis aphylla was found
to contain 2 percent (dry basis) of potassium nitrate.- Sabinin, Baslavska/a,
Belouesova, and Schocklender (60).
DTbo is ia
Analyses of samples of DTboisia hopwoodii-received from Australia
showed nornicotine to be the only alkaloid present, as follows: Leaves
3.31, leaves on twigs ,1,92, twigs without leaves 0.95, and larger stems
0.52 percent.-- Bowen (10).

From the steam-volatile fraction of extracts of cured tobacco leaves,
volatile bases other than nicotine amounting to at least 6.5 percent of the
total alkaloid content were obtained. The dipicrate of a base isolated
from this nornicotine fraction decomposed at 179.5-180.5 C. (uncor.).
This base reacted with nitrous acid and with benroyl chloride in the man-
ner described by Pictet and Rotschy (ref. 30 In 3-561) for nicotimine.--
Vickery and Pucher (85).

The volatile and nonvolatile alkaloid contents of the following species
of Nicotiana are given: acuminata, alata, chinensis, glauca, glutinosa,

dorffi, longiflora, paniculf.ta, plumbaginifoL1i, quadrivalvis, repanda,
rusbyi, rustica, sF.nder-.e, suaveolens, sylvestris, tabacum. The alkaloid
content of a number of hybrids is given.-- Shmuk and Khmura (68).

Nicotiana tabacu,_ normally contains nicotine but no anabasine, whereas
N. glauca contains only anabasine. When N. glauca was grafted on N.tabacum,
formation of the characteristic alkaloid proceeded in stock and scion with
a consideraoie increase in the anabasine content of the scion over that of
the control plant. Anabasine appeared to be formed in the stock also, When
N. tabPcum w.s grafted on N. glauca, nicotine was completely replaced by
anabesine in the scion while a trace of nicotine appeared in the stock.--
Shmuk, Kostov, and Boro7dina (o9).

When Nicotiana rustic was grafted to N. glauca, it lost nicotine and
accumulated anabsine.-- Shmnuk (63).

The grafting of nicotine-containing tobacco on the nicotine-free species,
Nicotiana glauca, resulted in olants in which the nicotine was completely
replaced. by anabasine.-- Evtushenko (22).

A study was rmde of the inheritance of nicotine and anabasine content
by Yicotiana tabacum x Nicotiana glauca hybrids, and interaction of stock
and scion when these species are grafted. In hybrids a change was noted
in the type of alkaloids with reference to position of the leaves.--
Kuz'menko and Tikhvinskaya (5).

Nornicotine was identified in the following species of Nicotiana:
benthamiana, ingulba, longiflora, palmer, sanguine, solanifolia,
suaveolens, sylvestris, and trigonophylla.-- Shm k(6).

A large iauwber of representative Nicotiana species cnd hybrids were
examined for alkaloids. All 29 of the wild species contained 1 or more
alkaloids. N. alata, bigelovii, gossei, and wigandioides apparently con-
tained only nicotineP. N. glutino._ 1aritims, otonhora, tomentosa, and
trigonophylla apparently contained only nornicotine. N. debneyi and glauca
contained largely d,l_-anabasine. In debneyi about 15 percent of the total
alkaloid was nicotine, whereas in glauca a much lower percentage of this
alkaloid was found. The remaining 1S species contained mixtures of nicotine
and nornicotine. Nicotine was predominant only in N. benavidesii, langsdorffi,
and stocktoni; in longiflora and plumbaginifolia it was not possible to de-
termine which of the two alkaloids was present in the higher concentration;
and in the rest nornicotine predominate.. No wild species studied had a*
much as 2 percent total alkaloid content, and most species had less than 0.5
percent. In 23 species 84 to 100 percent of the total alkaloid content was
taken up by the manein alkaloid. In crosses between N. tabacum, which contains
mostly nicotine, an. species whose alkaloid complex was made up largely or
entirely of nornicotinie, the hybrids contained mainly nornicotine, together
with small amounts of nicotine. The F1 and amphidiploid N. tabacum (nicotine)
x N.glauca (anabasine) contained mostly anabap.sine with some nicotine. In
one c jple of this FI a trace of nornicotine was detected.-- H. H. Smith
Pnd C. R. Smith (7).

A method is presented for classifying tobacco; broadly into three
tyrpes according to their picrate melting points-- (1) the


nicotine type, 215-2240C.; (2) the mixed type, 190-215, indica-
tive of both elkploids as mpjor components; qnd (3) the nornicotine
type, l75-200. Of 90 smunples of tobacco examined, 2 were of the
nornicotine type. One, Robinson's .!aryland Medium Broadlenf, was
investigated by Iiarkwood refss. 25 and 26 in Eb561)j the other,
Flue-cured Cash, may prove equally valuable as a source- material
of nornicotine. Two tobaccos were of the mixed type; the otters
were of the nicotine type.-- Markwood and Barthel (46).

The 42 species of Nicotiana, when analyzed by an improved pro-
cedure which is described, can be divided into 4 Froups as follows:
(1) The main alkaloid is nicotine, secondary pyridine alkaloids
being absent or present only in insignificant quantities; (2) the
main alkaloid is nornicotine, tertiary pyridine alkaloids being
absent or present only in insignificant quantities; (3) a mixture
of nicotine and nornicotine, and (4) the main alkaloid is anabasine.
-- Shmuk and Borozdina (67).

A simplified method is presented for the identification of
alkaloids of tobacco. The essence of the method is the formation
of the pirates of the secondary base and submission of it to
methylation without isolation of the pure amine; for effective-
ness it is sufficient to have 2 to 10 mg. of the alkaloid. The
pirate of the base is methylated quantitatively by heating with
formaldehyde and formic acid. The presence of nornicotine by
this procedure was shown in various members of the tobacco
family. Determination of the picrate melting point both before
and after methylAtion enabled the nornicotine to be identified
in the presence of nicotine. Anabasine and piperidine sre also
methylated by this procedures-- Shmuk (64).

In order to find a more logical basis for a classification
of tobaccos, the melting points" of pirates prepared from known
mixtures of nicotine and nornicotine were determined. The steam-
volatile alkaloids were separated from the plant material by dis-
tillation and the melting point of the mixed pirates of the alka-
loids was compared with that of the known-mixture pirates. In
the curve prepared from the known-mixture-picrate melting points
and composition the slope of the rigpht-hand side was sufficient
to warrant establishment of a division at composition two-thirds
nicotine and one-third norniootine, and temperature 211 C. Hence,
tobaccos, the alkaloids of which give a pirate with the upper
limit of the melting range above this point, are considered as the
"nicotine type." The division point at composition one-third
nicotine and two-thirds nornicotine, and temperature 1960C.,
falls in a region of marked discontinuity of melting-point be-
havior and is therefore even more suitable to set off the
"nornicotine type" of tobacco. This leaves the interval 196
to 211 C. as oharaoteristic of "mixed type" of -obacoo. Tobaccos
were analyzed for nicotine ard nornicotine, and the analysis and
the melting point of the pirate of the steam-volatile alkaloids
from the sample were compared with the composition-melting point
curve. The close agreement of the relative percentage compositions
and melting points obtained from the tobacco samples with t-:ose of
known solutions has been used with considerable success in extimat-
ing the relative composition of these alkaloids in samples.--Bowen
and Barthel (16).


Nornicotine may be identified in tobacco, insecticidal tobacco
preparations,and nicotine preparations by comparing the melting point
of the mixed pirates of the steam-volatile alkaloids with the picrate
melting point of a methylated sample thereof. Methylation of the nor-
nicotine gives nicotine; consequently, the picrate of the methylated
alkaloids will mqlt at the same point as nicotine picrate and no de-
pression of melting will occur in a mixed-melting-point determination
with nicotine picrate in those cases where steam-volatile alkaloids
other than nicotine and nornicotine are substantially absent.-Bowen
and Barthel (161.

When nightshade (Solanum nigrum, Datura stramonium, and tomato
plants, usually free of nicotine, were grafted separately on tobacco
(Nicoti'ana tabacum and N.rustica), they were enabled to form this
alkaloid and store it in the leaves an& fruit. Large quantities of
nicotine will form in the scions, if the leaves are removed from the
tobacco stock at the time of intensive growth of the scions and the
root of tobacco is p-resent. When tobacco is used as the scion in
graft upon the same plants, nicotine disappears entirely from the
graft system and cannot be detected in the stock or scion. When N.
glauca, which contains anabasine, was grafted on a tomato plant, as
much anabasine was formed by the scion as occurred in the control
plant of I. glauca raised under normal conditions.--Shmuk, Smirnov,
and IIin-(O).


Two commercial samples of nicotine sulfate were found to contain
nornicotine, in one amounting to nearly 12 percent of the alkaloid
content. This finding is important because nornicotine has been re-
ported to be more toxic than nicotine to aohids. Commercial nicotine
preparations containing nornicotine may be expected to be better con-
tact insecticides than those of pure nicotine. Since nornicotine is
known to be less volatile than nicotine, when a mixture of the two is
used as a fumigant, the predominant effect is believed to be that of
nicotine. The presence of nornicotine in materials considered to be
pure nicotine products could easily account for erratic and nonre-
producible entomological results.-- Bowen and Barthel (12).


Steam distillation under pressure can be used to remove anab-
asine from plant material.-- Sokolov (78).

Of the water-immiscible solvents for the extraction of anab-
asine, ethylene dichloride is the best for yield and for velocity of
extraction. Anabasine combines rapidly with the impurities in tech-
nical ethylene dichloride only during the initial stage of standing,
after which anabasine is not decomposed and is only partially trans-
ferred to the residue with the slowly separating products of the
reaction. The optimum ratio of solvent to raw material is 2:1. A
semi-production-scale apparatus and experiments are described.-
Sokolov and Trupp (81).

- 7 -

The diffusion process of producing anabaslne by the water-
kerosene method is described. Proteins, which are especially
harmful in the further treatment of the alkeloids, are decreased
sharply by the presence of sodium chloride. The maximum yield of the
alkaloids was 98 percent. In the countercurrent-diffusion process
the average period of extraction depends on the temperature of the
water it could be reduced to 20 to 30 minutes.-- Sokolov and
Demonterik (79).

A report on the production of anabasine sulfate from Anahasis
aphylla at Tohimkent, U.S.S.R., has been published.-- IlJin CSO).


Commercial anabasine sulfate solution is reported to contain
21*52 percent of anabasine, 7.52 percent of lupine. 10.45 percent
of aphyllidine and aphylline, 12.19 percent of total sulfates, 1.68
percent of free sulfuric acid, and 1.24 percent of inorganic im-
purities.-- Dashkevloh (19).

An improved method for the isolation of lupinine from commercial
anabasine sulfate solution was devised. The crude alkaloid mixture
was separated by the Orekhov method (ref. 98 in E-537) and distilled
in vacuo. The low-boiling fraction 136-9*Tp 12 mm.) consists of
upinine and anabasine. The mixture is dissolved in dry toluene and
treated with metallic solium with stirring and heating. On cooling
the sodium lupinate is filtered off, washed with dry toluene, and
treated with water, the mixture is extracted with petroleum ether,
and tV e.traot dried and concentrated to yield crystalline lupinine
(97 percent recovery). The mother liquor after distillation yields
anabaaihOe The use of petroleum ether for washing sodium lupinate
also appears to give a better product than toluene. The best resul4-
were obtained when petroleum ether was used as the medium for the
reaction with m+Plle io sodium.-- Sadykov and Lozur'ovskii (61).

In 1935 it was reported that Russia produced 2,500 tons of
insecticides (powders, soaps, and solutions) containing anabasine
or anabasine sulfate.-- Booharova (8).


A method for the microchemicoal detection of anabasine In
legal chemical investigations has been described. When Dragon-
dorf's reagent is added to solutions of anabasine, characteristic
crystals are obtained which may be used for the miorooahemical de-
tection of the alkaloid in material from the cadaver. In this way
as little as 1 microgram of anabasine in a drop of solution can be
detected. The anabasine is extracted from the organs by repeated
digestion of the ground material with alcohol to which tartaric
acid has been added in amounts sufficient to give an acid reaction
to litmus. The extract is concentrated in vacuum, the protein re-
umoved, the alcohol evaporated, and the material subjected to pre-
liminary purification with chloroform. The tartrate is then oon-
verted into the base by treatment with amonia, and the base is ex-
traoted with chloroform. After removal of the chloroform the an-
abasine can be tested for directly, or after further purification
of the solution.- Shvaikova (71).

A rapid method is proposed for determining total alkaloids
in semimanufaotured products and waste materials in the production
of anabasine. The alkaline extract is extracted with ethylene
dichloride and the ethylene dichloride extract titrated with
hydrochloric acid (litmus indicator)* For determination in
Anabasis the raw material is extracted with water, a part of the water
extract is made alkaline, and the analysis conducted as above.-
Sokolov (T7).

Separation of anabasine from nicotine and other alkaloids

A titration method for determining the total alkaloid content
of a mixture is proposed which is based on the fact that the acetyl
derivative of anabasine does not form a pirate and nicotine does*-
Khmura (L3).

Anabasine can be separated from the alkaloids associated with
it in Anabasis aphylla by precipitation as fluosilicate from a solu-
tion in ethyl or methyl alcohol. The fluosilicate, CjoHl4N2H2SiF69
H20, m.p. 239(dece), can be converted to the free base by reaction
with sodium hydroxide. Anabasine is precipitated with alcoholic
fluosilicia acid from an alcoholic medium. The precipitate is
dissolved in hot water and titrated with a 0.1 N sodium hydroxide
solution (thymolphthalein indicator). Nicotine-can be determined
similarly. Nicotine can be distinguished from anabasine by the
solubility of its fluosilioate in methyl alcohol; fluosilicates
of both are insoluble in ethyl alcohol.-- Sokolov (75, 77).

A comparative study was made of the reactions of anabasine, nico-
tine, and coniine. The Meltser reagent (carbon disulfide, ethyl
alcohol, and dilute copper sulfate solution) causes a white turbidity
with nicotine and a black-brown turbidity with anabasine and ooniineo
All three alkaloids form characteristic crystals in saturated aqueous
solution of picric acid. An ether solution of anabasine or nicotine,
when mixed with an ether solution of iodine, first becomes turbid
and then crystallizes* Coniine does not undergo this reaction.
Mecke reagent (selenic acid and concentrated sulfuric acid) colors
the anabasine residue pink, but does not change the color of nico-
tine or ooniine with hydrochloric acid (sp. gre 1.19). The ooniine
residue forms beautiful violet crystals after evaporation* No
such crystals are formed from anabasine or nicotine. With nitric
acid (sp* gre 1.4) the nicotine residue assumes on slow heating a
pink color, which change to green. Under the Sao conditions no
coloration of anabasine and ooniine is observed. A maximum yield
up to 95 percent of anabasine alkaloids is obtained by extraction
of cadaver material with acidified alcohol*-- Rasvadovskii (55).

The following directions for determining nicotine in the presence
of anabasine are givens Treat the aqueous solution of the alkaloids
with 3 ml. of 10-percent sulfuric acid and 10 ml. of freshly pre-
pared 5-percent sodium nitrite, heat for 30 minutes at1 40-50*
neutralize approximately by introducing 10-percent sodium hydroxide
and then accurately by titration with 0.1 N sulfuric acid (with
methyl orange), and add S to 4 drops of exc-ess acid. Precipitate
the pirates by addition of piorie acid (12 gm. per liter) and cool
for 4 hours. Filter, wash twice with 0.1-percent picrie acid and
twice with water, transfer to a glass-stoppered flask, add 16 to 20


mle of water, and titrate with a 0.1 N alkali (phenolphthalein in-
dicator), adding 5 *1* of toluene toward the end of titration. The
amount of O01 N sodium hydroxide used multiplied by 0.0081 gives the
content of nicotine. The method is based on the fact that nitrous
acid, without affecting the nicotine, transforms the anabasine into
the nitroso compound, which is not precipitated by pioric acid under
the above conditions.-- Shmuk and Borozdina (65).

Nicotine and anabasine, treated with an aqueous solution of
aniline and a 5-percent solution of ammonium thiocyanate or potassium
thiocyanate in bromine water, give a yellow color, whioh remains
constant after the addition of 0.5 to 3.0 co. of 5 to 10 percent
sodium carbonate for nicotine, and changes to a bright rose for
anabasihe. The colored solutions can be compared in the colorimeter
with corresponding standard solutions. However, the determination
of anabasine and nicotine by the colorimetric method in plants was
complicated by the other compounds containing the pyridine ring.--
Shmuk and Borozdina (66).

To identify the alkaloids of tobacco the pirates of nornico-
tine and anabqsine can he methylated quantitatively by heating with
formaldehyde-formi3 acid. Picrio acid does not methylate under the
conditions used. Determination of the melting point of the pirate
before and after methylation enabled nornicotine to be identified in
the presence of nicotine*-- Shnuk (64).

Nicotine forms an azeotropio mixture with water in a concentra-
tion of 2.5 gms per 100 mle This property is used in separating it
from norniootine or anabasine, or both. The separation of nicotine
from a mixture of the three alkaloids was 97 to 103 percent of theory
when the procedure consisted in distilling the mixed alkaloids from
125 mlo of water solution through the Widmer column to a low volume
(about 16 rl*), adding 60 mle of water containing 2 gm. of sodium
chloride, and continuing again to a volume of 15 mle The combined
distillate was titrated and calculated as nicotine, but represents
all the niobtine with some of the accompanying alkaloid or alkaloids.
The titrated distillate was made alkaline with a slight excess of
standard alkali to neutralize the standard acid, end the dis-
tillations were repeated as before but without the addition of
sodium chloride. The combined distillate was titrated and the
nicotine calculated.-- C. R. Smith (73).

The determination of nicotine and norniootine in the presence
of each other in aqueous solution is described. One portion of the
solution is treated with sodium nitrite and acetic acid. The nitroso-
nornicotine formed is not volatile in steam from a solution buffered
*t pU 10. The unchanged nicotine is sbeam-distilled off, and
determined by acldimetrio titration or lby precipitation with
siliecotungstio acid. To another portion formaldehyde and fodrmie
acid are added to methylote the norniootine to nicotine. The total
alkaloid, now nicotine, ib distilled off after addition of excess
sodium hydroxide and determined as before. The difference between
the two values represents the norniootine. Details were developed
tr attaining en accuracy of 97 to 98 percents- Markwood (465).

JA -. f, -ap1tud for the ciAazia diAtillation of niaotines
n i' ,i.. i. LL&.'L.&asine has 'een designed. This apparatus per-
mits a lrjge. co t between the esteem vapor and the solution con-
taii., the *..- ioida, which results in more rapid distillation than
is p1iL :11, *;h, c 0n1entional (A.O.A.C.) method.-- Bowen and
Narthsi (|D') ''

A... t.i i p.-Qokoed for analysis of nicotine and nornleotine*
i oh l ii atad strong sodium hydroxide greatly aid the distillso.
tion of nornioGtiae. The steam distillate containing both alkaloids
is eon.;jftrated, and an aliquant treated with nitrous acid to forn
nitroscijomiootine, which is not volatile with steam under the ooa
dit..ia at which the nicotine may be distilled (alkaline to phenol-
phtialein), Precipitation of the silicotungstates of the distillate
containing ne nicotine and of another aliquant containing both alka-
loids fu-Lishas the means of calculating the percentages of these al&ka-
loids* Th3 results of analyses of several samples of tobacco N. ruestia,
andvieroial nicotine sulfate solutions indicate an unezpeotedTy wide-
spread ocorsnja of nornicotine. From a comparison of analyses mad*
according to the A. 0. A. C. method, it is evident that when nornicotine is
present thi accepted method of analysis for nicotine cannot be de- .
ended tpoa to give reliable results.- Bowen and Barthel (13)

A teat for the completeness of extraction of alkaloids frcm
plant iatetial is described which employs a slight modification
of the method taployed by Markwood and Barthel (see 46) for the
liberation of the alkaloid from plant material. Aproximately
5 Sn. of thaiiiax is treated with 10 ml. of strong sulfuric acid
(9 + 1)p whereby the cellular structure is broken down with the
formation of the sulfates of any remaining organic bases. After
mixing for several minutes, water is added and the undissoled
portion removed by filtration. The filtrate is neutralized witkh
sodium hydroxide just aoidifed with hydrochloric acid and tested -with.
siliootungstic acid solution. The test solution and reagent am
warmed and then cooled with strong agitation. No precipitate in-
dicates leus than 0.01 percent of nicotine, nornicotine, or anmbasim
- ciad Biaetfiil (14).

A ,ti.iU3 of detrudining nicotine and norniecotine in mixtures of
the alksIlia i without preliminary separation is described* The soft"
depeadu .:-i I\. raeaotions of these compounds with cynogen bromide
to gii with nicotine, a pale yellowish-green color, and with
nu,.:nijt1nW a red color. A 0.5-4 to 2-l6 sample of tobaceo is steam-
diiitillj faoLj a 4ilution containing salt and sodium bydrexide. 2hS
treatn, insures a quantitative recovery of nornieotine, whidh is ah,
laei v.AkuAle with steam than is nicotine* A volue of the dis-
till. ti .ji.iAat g not more than 80 micrograms of nicotine or 160
, ,-.t ,f *j(. d i cotine is treated with o stassium dihydrogen
pbh i .h .. an.1 then with freshly propwe cyanogen bromide reagente
Arr ;.h, _-olu.: has been allowed to develop, the solution is trans-
f :; ,..j S a putrophotometer and the intensity of the -eolor do-
vil-.1 Lt nicotinee is read at 540 millimicrons and that by
^,,U, a-i 5'76 idllibiorons. Concentrations of the alkaloids siw
det. jk I i y laspeotion of previously prepared ealibration Mur*sV .
Sino iLiao o.olor developed by nornicotine has an additive effect oali
intenSlty of thU otlor given by nicotine, the true *oncentratioma ef

- 11 -

nicotine is equal to its apparent concentration minus the concentra-
tion of nornicotine. Factors influencing the development of the
colors are discussed.-- Larson and Haag (37).



Farmers in the Union of South Africa believed Nicotiana glauca
to be deadly to ostriches, and it. had been reported to be poisonous
to cattle and sheep. In tests on rabbits the flower were found to
be slightly less toxic than the leaves. Rabbits died within 1.5
hours after being fed 30 gin. of the fresh flowers and within half an
hour of eating the same dosage of fresh leaves. A sheep receiving
300 gn. of the fresh leaves through a stomach tube died within 2.5
hours.-- Steyn (84).

Anabasine solutions are fatal to animals-when injected under
the skin. Solutions of the equivalent compound anabasine-proto acid
(obtained from soybeans and pea seeds) under the s me conditions
cauqpd only slight poisoning. The rule of Traube stating the relation
between the surface tension of a solution and its poisonous properties
cannot be applied to solutions of anabasine-proto acid, since in spite
of low surface tension such solutions do not kill experimental animals,
Leont'ev and Smirnova (39).

Alpha-aminoanabasine possesses the fundamental pharmacological
properties of anabasine but is less active. Its depressing action
on the sympathetic ganglion of white mice is 1/75, its stimulating
action on the cerebral layer and the kidney 1/75, its stimulating
action on respiration 1/20 to 1/100, and its toxic action 1116. The
primary phase of the depression of respiration is absent; action on
the blood pressure of decerebrate cats is less, and production of
convulsions in white mice is greater, than with anabasine.-- Poluektov

The introduction of acetyl, proplonyl, and benzoyl groups in
alpha- and alpha'-amino-N-methylanabasine decreases their respiratory
stimulation but does not lower their toxicity.-- Eabachnik and
Zitser (2).

The intravenous injection into rabbits of 2.5 to 6 rm. of ana-
basine sulfate per kilogram of body weight followed by repeated in-
jections of 0.5 to 1.5 mg. per kilogram caused a decrease in the
velocity of blood circulation in the lesser circulation system. The
decrease was due to the action of anahasine sulfate in contraction
of the blood vessels and the increased emission of adrenaline.--
Pleshchitser (U2).


On lice and dogs the toxic and vasopressor effects of smoke
from a tobacco containing 0.13 percent of nicotine and 0.27 percent
of nornicotine were due to the nicotine present, and relatively in-
dependent of the nornicotine content of the tobacco. On man the
smoke from these low-nicotine cigarettes produced much less pro-
nounced effects on blood pressure and pulse rate than did Fmoke from
ordinary cigarettes.- Haag and Larson (26).

-12 -

A comparison has been made of the toxicity, the blood-pressure
effects, and the fate in animals of levo-norniootine, levo-niootine,
monomethylniootiniumn iodide, isomonomethylnicotiniu iodide, and
dimethylniootinium iodide. The integrity of the pyridine nitrogen
appears to be essential to the high toxicity of nicotine and its
methylated and demethylated derivatives. Progressive methylation
of the pyrrolidine nitrogen increases the toxicity, as determined
by intraperitoneal injection in mice, in the ratio 1:2s4 for nor-
nicotine, nicotine, and monomethylnieotinium iodide. Difference
in the dissociation constants of the three bases may be the ex-
planation. In dogs the pressor effects of nornicotine and mono-
methylniootiniun Iodide are, respectively, one-twelfth and two-
thirds those of a molecular equivalent of nicotine. Isamonomethyl-
nieotinium iodide and dimethylnicotiniun iodide have practically
no pressor action. The metabolism, In dogs, of the methylated and
demethylated derivatives appears tc be different from that of
nicotine*. No evidence was found that detoxication of nicotine in
the animal body involves either methylation or demethylation.-
Larson and Haag (36).


Niootiana tabaou, N. rustica, and N. glauoa are mentioned
as poios -or cmbating an= and planT pe s. Sprenger (83).

Dipyridyls tested as contact insecticides were toxic to six
species of aphids (bean, spinach, pea, turnip, apple, and rosy
apple), adults and larvae of the Colorado potato beetle, and
larvae of the three-lined potato beetle, the Mediterranean flour
moth, and the silkworm, A crude dipyridyl oil [now known to have
contained some neonicotine or anebasine] was more toxie than
nicotine to certain insects.- Richardson and Smith (

The alkaloids of Sophora are intermediate between anabasinez
and lupine in insecticidai-power.- Sokolov and Koblova (Q0a

The results of tests with anabasine on several species be-
longing to the orders Thysanoptera, Hamoptera, Hemiptera, Dipteoz
Coleoptera, and Anoplura have been reported in the last six yearss*


Control measures for Helioti haeAmorrholdalis (Bouoh5) In
Russia included thorough spraying ofthe infested plants tw or three
times at intervals of 10 days with 0.5-peroent nicotine sulfate or
anabasine sulfate in 1-percent soap solution.-- Voitenke (86).

In Russia spraying with 7 to 10 @. of anabasine sulfate awd
40 V0 of soap in 40 liters of water was effective against adult
thrips on mature flax.- 8Smeleva (62).

A marked reduction in infestation by Thrp lini LAd.(linarius
Usel) and a considerable increase in yield ofTlax ean be obWied-
with a spray containing 0.3 or 0.2 percent of anabasine sulfate in
0*.4pereent soap solution, or with a dust containing 6 percent of
anabasine sulfate.- Irmoloev (e).

- 13 -

Free anabasine at 1:1000 and 1:2000 and anabasine eulfate (4O
percent anabasine) at3:600 and 1:500, with and without sugar,
showed high toxicity to the citrus thrips in laboratory experiments
at Whittier, California. Sugar or some other added material is
probably ,of value in retarding the loss of the toxic material. The
thrips do not seem to feed on the anabasine-sugar residues. The
material appears to act by contact and by fumigation. Although
citrus thrips do not need to come in contact with the anabasine res-
idue to be killed, the indicated range of the fumigation effect is less
than a half-inch. The thrips underwent convulsions, followed by paral-
ysis,. within 9 to 14 minutes after their exposure to anabasine.--
McGregor (40, 12).

In orchard tests in the San Fernando Valley (Calif.) anabasine
sulfate (1:600) with blood albumin gave marked reductions in the
strain of citrus thrips resistant to tartar emetic. In similar tests
at Whittier anabasine sulfate with sugar and with blood albumin gave
high mortalities of the nonresistant strain. No injury to tender
lemon leaves was detected from liquid applications of anabasine or
anabasine sulfate.-- McGregor (41).

Tartar emetic was formerly the perfect control for citrus thrips,
butV a resistant race of thrips has developed. The best alternative
at present is nicotine and sugar, which is satisfactory on lemons.
The sulfate is superior to the alkaloid. Some work has been done
with anabasine, but there is no clear-cut evidence that it is better
than nicotine.- Boyce (17).

Anabasine sulfate is recommended for use against thrips attacking
flax and hemp in Russia.-- Nikiforov (48).


The toxicity of anabasine was about equal to that of nicotine
against aphids.- Freak (23).

An infusion and a decoction of thkleaves of Nicotiana glauza
with soap (1 pound of leaves to 50 gallons of water) had a very
slight effect on nasturtium aphids, while the powdered leaves had. r,
apparent effect on them. The nicotine content of the leaves, de+er-
mined upon a moisture-free basis, was only 0.18 percent.-- 4cladco
and Sievers (43) [This plant contains anabasine, not nicotine,--
E. C. R.]

Amabasine sulfate mixed with beeswax and a fatty oil was urne of
the materials tooted at Wenatehee, Wash., in experiments to prevent
Eriosoma lanigArum (Hausm.) from infesting wounds in apple trees.
To injury to plant tissues resulted from the application, but the
effect oR the aphids is net recorded.-- Reeves, Yothers, and Murray
A spray containing anabasine sulfate (40 percent onabisine) at
1 to 1,000 in th. first half of the season on lucerne (alfalfa],
acacia, and cotton infested with (Dorails) Aphis laburni Kalt. and
other cotton aphids gave excellent results In the] t oaV- Rekach

- 14 -

A combination of solbar (barium polysulfide) and anabasine
sulfate oan be used for the simultaneous destruction of cucumber
mildew and aphids. [These materials will react to form barium
sulfate, free anabasine, and free sulfur.-- R. C. R.] A solution
containing 0.5 percent of green soap and 0.3 percent of anabauine
sulfate killed all the aphids.-- Zubov and Vasilevskii (87).


Conoentration-nortality curves are given for solutions of various
ni)rogenous bases and soap when applied to the eggs of Lygaeus kalmnii
Stil, and the data are analyzed statistically. The folWgmedia
lethal concentrations were obtained: Nicotine 0.11, quinoline 0.12,
anabasine 0.18, piperidine 0.29, pyridine 19.6, and sodium oleate 2.0
percent. Quinoline was the only compound that killed the eggs at
once. The others permitted development of the embryos to continue
for several days. In some cases the young bugs were able to emerge
from the eggs but died soon after hatching.- C. F. Smith (72)e


Of the stomach larvicides tested on Luoilia ourina MWed. in
Australia, anabasine sulfate (40 percent anabasine a toxil at
0.1 percent concentration, whereas nicotine sulfate was toxic at
0.01 percent.- Lennox (mal

In tests by P. M. Petrov of sprays against (Mayetiola) PhtphaPa
destructor (Say), preparations of anabasine gave the best results an
were effective against the eggs.-- Ostapetz (49).

The effects of aerosols of anabasine sulfate and anabasine on
Anopheles mosquitoes were investigated. The mosquitoes were very
sensitive to anabasine solutions. The minimum lethal dose was 0.2
gmu. of anabasine per cubic meter. The aerosol possesses an un-
pleasant odor, producing coughing, but under summer conditions it
is dispersed rapidly and no odor remains after 15-20 minutes. To
accelerate the reaction at low temperatures the mixture must be
heated or some fty lime and ,bilfuric acid added. Anabasine may be
volatilized by adding the free base or the sulfate to sand heated
to 300-350%. The aerosol had no harmful effect on rabbits and hens,
on the germinating properties of seeds, or on food products.-
Pogodina and Sokolov (5).

The toxicity of anabasine to mosquito larvae was muoh inferior
to that of nicotine.- Freak (2e),

The toxicity indices of anabasine sulfate (55 percent anabasine)
to Drosophil ampelophila Loew were determined in three kinds of baits
as follows In apple sirup 14.0, in molasses 7.2, and in sane sugar
and glycerin 30.7, Sodium arsenite in the respective baits gives the
following indices 78.6, 62.8, and 63.7.- Patterson (50)

- 16 -

In t-L t& aLaidt the s Uner cabbage fly in Russia, the per-
centagar of eggsa destroyed by three applications of mercuric
ahloride (I:I000) were 95.*, of anabasine sulfate plus green
soap 79 S9, .nd of nicotine sulfate plus soap 76.0. The percentages
of fi.t iLstax8 destroyed by these three solutions were, re-
spectively, 6,61, 2.6, and 3.6. They had no effect on the second
and third instars-- Galakhov (2.0

When housefly eggs were dipped in an aqueous solution con-
taining 3 percent by weight of anabasine, the mortality was within
the same range (0 to 30SO percent) as that caused by a solution con-
taining 5 percent by weight of nicotines-- Riehardson (59).


hynhites baoohus L.# (Coenorrhinus) R. .i__llus Germ., and
Antho6namu pmorm (L"J are iapo73 pestsoWTfat trees in Russia.
aDusting wit calcium arsenate containing 7.5 percent of anabasine
sulfate, or with a proprietary arsenical (Meritol), at rates of 13.5
and 27 pounds per acre, respectively, proved effective against all
three species on apple*- Ibatulina (29).

A solution containing 2 percent of anabasine sulfate and 0.5
percent of green soap man completely effective against head lice,
and had no harmful effect on the scalp.-- Pivoyaror (51).


Anabasine tannate is made by reacting 17.5 pounds of anabasine
and 116 pounds of Chinese gallnuts in the presence of water. The
product is insoluble in water and contains about 12 percent of the
alkaloid. This patent covers the tannates of nmethylanabasine and
of the mixture of alkaloids obtained fram Anabasis aphylla.- Arnold

Anabasine bentonite is made in the same way that nicotine
bentonite is made. Wymaing bentonite is treated with an excess of
anabasine sulfate solution. After drying, the product contains
about 14 percent of the alkaloid, of which one-half is water-
soluble. Nornieotine bentonite may be made in the same mamer.-
Arnold (2 4,506).

Anabasine and nornlcotine may be substituted for nicotine in
a dusting powder made by volatilising the alkaloid, mixing it with
exhaust gases, and bringing the mixture into eontaeot with a dust
suspended in gas* Suitable tunigati ng and dusting apparatus for
treating a tree under a tent are described.-- Arnold (0.

An inseetioidal dust is made by adding frcm 8 to 20 percent
of free anabasine or nornicotine to an alkalinized tobacco dust
as a carrier and mixing 30SO pounds of this with 70 pounds of elay.
Arnold (.

Auabasine can be dissolved in Freon-12 and applied as an

- 16 -

aerosol.*- Goodhue and Sullivan (25).

Nicotine, anabasine, and nornicotine are among the insecticides
mentioned that can be used in combination with 2,3-dithiocyano-2,4,4-
trimethylpentane for pest control, especially as a fly spray.-
Bousquet (9).

Derivatives of benzotetronic acid, including benzotetronie acid-
alpha-carboxylic acid anabaside (made by combining the free acid and
anabasine), are suitable insecticides for mothproofing wool.-- Martin

Fatty acids from tung, linseed, fish, soybean, and other drying
oils react with nicotine to form water-insoluble, nonvolatile, sticky
fluids suitable for insecticide use.-- McKinney (44). rAlthough no
mention is made of anabasine or nornicotinp, they could be similarly
used.-- R. C. Roark]

An insecticidal powder is made by mixing anabasine with a high-
ly dispersible acid clay of limited adsorbing capacity.-- Dashkevich


(1) Arnold, R. B. 1933. New insecticide material. U. S. Patent
1,925,225, Sept. 5. To Tobacco By-Products and Chemical Corp.

(2) ---- 1940a. Insecticide and process of making the same. U. S.
Patent 2,219,287, 00t. 29.

(3) ---- 1940b. Method and apparatus for distributing parasiticides.
U. S. Patent 2,222,598, Nov. 26.

(4) --- 1945 a. Insecticide spray material and method of making the
same. U. S. Patent 2,311,629, .Feb. 23.

(5) ---- 1943b. Insecticidal spray material. Canadian Patent 412,655,
May 18.

(6) --- 1944&. Spray material and method of making the same. U. S.
Patent 2,343,559, Mar. 7.

(7) -- 1944b. Parasiticidal dust for contact use and process of
making the same. U. S. Patent 2,343,560, Mar. 7.

(8) Bocharova, S. J. 195o. [Results of the work on anabasine.]
Selsk. Khoz. Nauka Kazak. (Agr. Soi. Kazak). Nos. 1-2, pp.

(9) Bousquet, E. W. 1944. Pest control. U. S. Patent 2,342,448,
Feb. 22. To E. I. du Pont de Nemours and Co.

(10) Bowen, C. V. 1944. Insecticidal possibilities of Duboisia
hopwoodii. (Scientific Note) Jour. Econ. Ent. 37s T'9.

- 17 -

(11) -- and Barthel, W. F. 1943a. Improved steama-distillatioa
apparatus. Indus. and Zngin. Chem-., Analyt. 2&. 15: 596,
(12) -- and Barthel, V. F. 1943b. Nornicotlne in commercial
nicotine sulfate solutions. (Scientific Note) Jour, Icon.
hnt. 36; 627.
(13) -- and Barthel, V. 7. 1943c. Determination of nicotine and
nornicotine in tobaccos. Indus. and Ingin. Chem., Analyt.
3d. 15; 740-741.
(14) ---- and Barthel, W. F. 1944a. Tests for completeness of ex-
traction of tobacco alkaloids from plant materials. Aassoc.
Off. Agr. Chem. Jour. 27s 224.
(15) a-- nd Barthel, V. 7. 1944b. Classification of tobacco,
nicotine-nornicotine method. Indus. and Zngin. Chem. 361
(16) -- and Barthel, V. F. 1944c. Identification of nornicotine
in tobacco. Indus. and Zngin. Chemo, Analyt. 3d. 16: 377-378.

(21) Boyce, A. M. 1944. Up to now with citrus insecticides. Calif.
Citrog. 291 117.
(18) Daehkevich, B. N. 1934. Description of the method of prepara-
tion of a powdered ineecti-fungicide. Ruesian Patent 49,091,
Nov. 30.
(19) -- 1939a&. The chemical properties of commercial anabasine
sulfate. Trudy Leningrad. Inst. Sovet. Torgovli 1939 (2):
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Abs. 37: 3228. 1943.]
(20) --- 1939b. The chloro- and bromo-substituted anabasine alkaloids
and their structure. Trudy Leningrad. Inst. Sovet. Torgovli
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1941; Chem. Abe. 37: 3095. 1943.J
(21) Irmoloev, N. F. 1940. The biology of Thrips [lini Lad.] linarius
Us. and control measures against it [LeningradJ Inst. Za7ich
Bast, (Lenin Acad. Agr. Sci., U. S. S. R., Inst. Plant Pro-
tect.) Trudy po Zashch. Rast. (Bul. Plant Protect.) 3: 23-24,
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(22) 3vtuehenko, G. A. 1940. The most important results of the
investigations of the physiological section of the Tobacco
and Machorka Institute (WITIM), Tabakwelt 10 (6): 32-41.
[In Russian. Abstracts in Chem. Zentbl. 112 (1)t 591.
1941; Chem. Abs. 36: 7066. 1942.]
(23) Freak, G. A. 1942. Insecticides. Chem. and Indus. 61t 429-.431.
(24) Galakhov, p. N. 1941. Combating the summer cabbage fly. Sady
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Abstract in Chem. Abe. 3 = bIn.1sian

- 1S -

(25) Goodhue, L. D., and Sullivan, W. N. 194. Method of aplying
parasiticides. U. S. Patent 2,321,023, June 8. To Secre-
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(26) Haag, H. B., and Larson, P. S. 1943. Some chemical and phar-
macological observations on slow nicotine" tobacco. Science
97: 187-188.
(27) Higbee, B. C. 1942. Insecticidal plants in the Americas. Pan
Amer. Union Bul. 76: 252-257, illus.
(25) Holman, H. J., ed. 1940. A survey of insecticide materials of
vegetable origin. 155 pp. London. (Imperial Institute,
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(29) Ibatulina, P. S. 1939. Testing methods for controlling the
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(30) Iljin, M. 1939. Les buts et l'orieltation des travaux de la
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(51i) Jackson, K. E. 1941. Alkaloids of tobacco. Chem, Rev. 29:
123-197, illus.
(32) Kabachnik, M. I., and Zitser. A. I. 1940. Aminoanabasines. V.
Aminomethylanabasines and their acyl derivatives. Jour. Gen.
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(33) Khmura, K. F. 1939. The determination of nicotine and anabasine
when present in a mixture. YsesolUzn. Nauch. Issled. Inst.
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[In Russian. Abstract in Chem. Abs. 34: 4g62. 194o.]
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content of Anabasis aphylla and the biological-ecological
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Ito. 9; 66; Chem. Abs. 34: 6325. 1940J
(35) Kustmenko, A. A., and Tikhvinskaya, V. D. 1940. Inheritance
of nicotine and anabasine content by Nicotiana tabacum-
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when these species are grafted. Akad. Nauk. S. S. S. R.
(Acad. des Izv. Sci. U. R. S. S. Bul.) o. 4: [5641]-575,
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Chem. Abes. 35: 401*. 1941.]

- 19 -

(36) Larson, P. S., and Haag, H. B. 1943. Studies on the fate of
nicotine in the body. III. On the pharmacology of some
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(37) ---- and Haag, H. B. 1944. Determination of nicotine and nor-
nicotine in mixtures. Indue. and. Engin. Chem., Analyt. d..
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(35) Lennox, F. G. 1940. Studies of the physiology and toxicology of
blow-flies. 2. The action of stomach larvicides on Lucilia
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(39) Leontlev, I., and Smirnova, M. 1936. Pharmacodynamic action
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[In Russian. Abstracts in Chem. Zentbl. Ui0 (I): 175-176.*
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(41) 1943, Anabasine and Gesarol vs. citrus thrips. Calif.
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(42) --- 1944. Toxicity of anabasine to the citrus thrips. Jour.
Icon, Int. 37: 78-80.

(43) Mclndoo, N. 2., and Sievers, A. 7. 1924. Plants tested for
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(46) ---- and Barthel, W. FP. 1943. Tobacco classified according to
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29: 576. 1941.]

- 20-

(50) Patterson, N. A. 1935. Indices of toxicity for various poisons
to Drosophila ampelophila Loew. Bnt. Soc. Ontario, Ann. Rpt.
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(51) Pivovarov, V. M. 1940. Anabasine sulfate as a remedy against
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(55) Razvadovskii, V. A. 1939. A comparative study of the re-
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(56) RIekach, V. N. 1938. Cotton aphids of the south of the
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[In Russian. English summary, p-. 82-84. Abstract in
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(57) Reeves, E. L., Yothers, M. A., and Murray, C. W. 1939.
Unusual development of apple perennial canker, following
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