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the Dryabalanops camphora examined by Pelouze, which is associated with borneol ;
and it is doubtful whether the camphor dissolved in the camphor-oil which Martius
examined was common camphor, or borneol (as supposed by Gerhardt, N. Ann. Chim.
Phys. 7, 284), since, in 1838, the distinctive characters of the two kinds of camphor
were not known with certainty. Commercial, dark wine- yellow camphor-oil, of sp.
gr. 0'945, is a mixture which deposits a large quantity of camphor by cooling or
spontaneous evaporation. When subjected to fractional distillation, it leaves, after J-
has passed over, a residue which contains a larger quantity of camphor and solidifies on
cooling, while the distillate, on being redistilled till ^ has passed over, yields rectified
camphor-oil free from camphor. This oil is transparent, colourless, strongly refracting,
mobile, smells like camphor and cajeput-oil, and has a density of about 0'91. It
contains 82'03 p. c. C, 11'35 H, and 6'62 O, and according to Martius is C 20 H 16 O.

Rectified camphor-oil evaporated in a watch-glass leaves resin but no camphor. It
does not appear to take up oxygen, but absorbs dry hydrochloric acid gas, with rise of
temperature, forming a wax-yellow liquid, which fumes from excess of hydrochloric
acid, and when cooled to 8, solidifies to a soft butter, without depositing crystals.
When dry chlorine gas is passed through the rectified oil, it assumes a transient ruby-
red colour, gives off hydrochloric acid, and forms, after washing with water, an oil
similar to that produced by hydrochloric acid.

Rectified camphor-oil (probably that of Martius, Kr.) is C 20 H 16 O, and is converted
into camphor by nitric acid. (Macfarlane, Ann. Pharm. 31, 72.)

In light yellow camphor-oil of unknown origin, which yielded no camphor when
distilled alone, and only traces when distilled with water, Mulder (J. pr. Chem. 17,
106; Ann. Pharm. 31, 71) found, after drying over chloride of calcium, 80'41 p. c.
C, 10'84 H, and 8'75 O, and accordingly regarded it as a mixture of common camphor
and a non-oxygenated oil, C 20 H 16 .

C. Madder Borneene from Madder Fusel-oil. The fusel-oil contained
in the alcohol produced by the fermentation of madder-sugar yields
liquid products when distilled at temperatures rising to 230, while at
higher temperatures Isevo-rotatory borneol sublimes. From the former,
by digestion with caustic potash, then with chloride of calcium, and
repeated fractional distillation, a liquid may be separated which boils at
160 3 , contains 88'23 p. c. C, and 1T81 H, has a vapour-density of 4 85,
and is probably therefore borueene C 20 H 16 . (Jeanjean.) Lsevo-
rotatory borneol from madder fusel-oil yields by distillation with anhy-
drous phosphoric acid, a hydrocarbon smelling like oil of bergamot and oil
of lemon (Jeanjean), which, according to Gerhardt's statements (p. 313),
should be identical with madder borneene.

Appendix to Valerene.

1. Crude Oil of Valerian. Constituents (pp. 312, 313.) According to the
(older) statements of Kraus, it is an oxide of oil of turpentine C 30 H 24 ;
according to Ettling (Ann. Pharm. 0, 40) it is a mixture of oxygenated


and non-oxygenated oil. According to Hurault (N.J. Pharm. 12, 96),
the oil does riot exist in the root ready-formed, inasmuch as ether does
not extract any of it, but is produced from the root bv the action of
water. The same view is maintained by Bouchardat, but Pierlot con-
siders it erroneous.

Properties of the crude oil. Mobile oil, of pale yellow, or greenish to
yellowish brown colour. (Trommsdorff, N. Tr. 18, 1, 3.) The root of
the plant growing in woods yields a green oil, that which grows in
marshes a yellow oil. (Pierlot.) Roots a year old yield 1-82 p c. of oil
(Bley, Eepert. 48, 84). Sp. gr. O'OO to 0'96 (Zeller); 0'936 at 10.
(Pierlot.) It does not solidify at 40, but at 15 it deposits white
flocks of valerianic acid. (Pierlot.) Its odour is fresh and agreeable,
strong and pungent, like camphor, It is neutral, either in the fresh or in
the rectified state (Gerhardt) ; acid (Zeller, Pierlot, and others). It is
resolved into its constituents by distillation, as described at page 313.

Oil of valerian resinises when exposed to the air, acquiring an un-
pleasant odour, and forming valerianic acid, in consequence of its contain-
ing valerol. (Gerhardt.) After the ready-formed valerianic acid in the
valerian-oil has been removed, it is not possible by any means to obtain
an additional quantity of that acid from the oil. When oil of valerian
is exposed to the air, the greater part of the non-oxygenated oil, of the
valerianic acid, and of the water escapes, and the oxygenated oil becomes
resinised. (Pierlot.) It dissolves iodine with evolution of heat, giving
off a small quantity of greyish yellow vapours, and acquiring a dark red-
brown colour. (Zeller.) With pt. of nitric acid at 24, it turns
violet (Bonastre, J. Pharm. 12, 66); blue, afterwards yellow, acquires a
viscid consistence ^Rochleder), and forms oxalic acid. (Bonastre.)
According to Rochleder, it does not form oxalic acid, but on distilling the
mixture, it gives off nitrous acid, and forms common camphor precipitable
by water, a volatile substance which attacks the eyes strongly, a less
volatile body which reddens potash-ley, and a fixed yellow resin.
When oil of valerian is heated with nitric acid, a blue resin is formed,
heavier than water, insoluble in alcohol and in potash-ley, and similar to
that which exists in the root ready-formed. (Pierlot.)

With oil of vitriol, it turns dark brown-red to violet; with bichromate
of potash and oil of vitriol, greenish. (Zeller, Studien uber other. Oele,
Landau, 1850.) Oil of valerian treated with potash-ley, yields a resin
and a neutral oil which forms common camphor with nitric acid. (Roch-
leder, Ann. Pharm. 44, 1.) It does not form any compound with caustic
potash or soda. (Pierlot.)

Oil of valerian dissolves in an equal quantity of alcohol of sp. gr. 0*85,
and in every proportion of absolute alcohol. (Zeller.)

28. Xanthoxylene.

STENHOUSE. (1858.) Pharm. J. Trans. 17, 19; Ann. Pharm. 104,
236; J. pr. Chem. 73, 179; Chem. Centralll. 1858, 237.

Source and Extraction. In the seed of Spanish pepper (Xanthoxylum
piperitum, Dec.}. The bruised seeds are distilled with water ; the oil,


mixed with solid xanthoxylin, is collected and cooled, the separated
xanthoxylin is removed by filtration, and the oil is dehydrated with
chloride of calcium and rectified over potash, then over potassium.

Properties. Colourless, strongly refracting. Boils at 162. Has an
agreeably aromatic and persistent odour.


20 C 120 .... 88-23 88-08

16 H .. 16 . 11-77 11'60

136 .... 100-00

Xanthoxylene forms a liquid compound with hydrochloric acid.

Appendix to Oils Isomeric with Oil of Turpentine.
(Oil of Wormseed and its Products of Decomposition.)

Oil of Wormseed.

TROMMSDORFF. (1819.) N. Tr. 3, 1, 312.

VOLCKEL. Ann. Pharm. 38, 110; abstr. Repert. 80, 176. Ann. Pharm,

87, 312; abstr. J. pr. Chem. 61, 515. Ann. Pharm. 89, 358.
ZELLER. Stud, iiber either. Oele, Landau, 1850.
HIRZEL. Zeitschr. f. Pharm. 1854, 3; 17; 65; 80. Ibid. 1855, 2; 33;

49; 65; 81; 98; 114; 130; 144; 161; 179.

Wurmsamenoel, Oil or Essence of Semen contra, Oleum cinee.

Source and Extraction. In Levant and Barbary wormseed, the un-
expanded flower-buds of Artemisia Vahliana Kosteletzky, Artemisia contra
Vahl, and Artemisia Siberi. It is obtained by distilling the bruised
wormseed with water. The water which passes over with the oil con-
tains acetic acid. (Wunder, J. pr. Chem. 64, 499.)

Properties. Transparent and colourless to pale yellow (Trommsdorff
and others) ; pale yellow to brownish yellow. (Zeller.) The crude oil
is brownish yellow ; that which is obtained by distilling the seeds -with
milk of lime, and boils between 160 and 170, is transparent and colour-
less (Hirzel); after distillation over hydrate of potash, it boils at 180,
and is transparent and colourless. (Volkel.) Mobile (the crude oil is
slightly viscid). (Hirzel.) Sp. gr. 0'9258 at 11 (Wackenroder, Kastn.
Arch. 11, 78 ; N. Tr. 14, 2, 3) ; 0-936 (Volkel) ; 92 0-93 (Zeller) ;
0-946 at 11. (Hirzel.) The oil rectified over hydrate of potash, and
boiling between 175 and 180, has a sp. gr. of ; 919 at 20 (Volkel) ;
that which is obtained from the seeds by distillation with milk of lime
has a sp. gr. of 0*945 at 8. (Hirzel.) Boiling point of the crude oil,
170 220 (Volkel); 175 180 (Hirzel); of the rectified oil, 175.
(Hirzel.) The oil treated with alcoholic potash and then distilled with
water, boils at 175 (Volkel); that which is obtained from the seed by


distillation with milk of lime, begins to boil at 160, boils chiefly between
175 and 177 ; after rectification, between 174 and 175. (Hirzel.)
It smells like the seeds (Hirzel) ; more like camphor than the seeds
(Trommsdorff) ; wormseed oil from Baltimore smells more like cheno-
podium. (Buchner, Repert, 12,438.) Its taste is sharp and somewhat
bitter (Trommsdorff) ; burning and aromatic. (Wackenroder.) It
reddens litmus (Zeller) ; is neutral. (Hirzel.)








24 C

...114 ....


... 78-44 ...

. 77-89 ....

79-83 ...

. 78-92 ...

. 78-49

20 H

... 20 ....


10-65 .

. 10-58 ....

11-31 ...

. 11-43 ...

. 11-40


... 16 ....


... 10-91 ...

. 11-53 ....

8-86 ...

. 9-65 ...

. 10-11

C 24 H 20() 2 ....180 .... 100-00 100-00 .... 100-00 .... 100-00 .... 100-00 .... 100-00

a the first; b the last distillate corresponding to the formula C 18 H 15 O 2 ("Volkel);
the first distillate corresponds to the formula C 10 H'O, according to which 3 At.
oil = C 30 H 21 O 3 , by giving up 3 At. H and taking up 3 At. O, forms santonin
C^'H^O 6 (Heldt, Ann. Pharm. 63, 55); c, the oil rectified over hydrate of potash,
corresponds to the formula C 24 H 20 O 2 ; d. oil obtained from the seeds by distillation
with water ; e. with milk of lime ; the former corresponds to the formula C 22 H 19 O 2 , the
latter to the formula C 20 H 18 O 2 . (Hirzel.)

Wormseed oil is mixed with another oil which changes even by distillation (Voikel) ;
it is a mixture of cinsebene, cineebene- camphor, a small quantity of propionic acid, and
oxide of propyl, the differences in its properties being due to the varying proportions of
their constituents. (Hirzel.)

Decompositions. 1. When set on fire, it burns with a clear luminous
flame. (Volkel, Hirzel.) 2. It dissolves iodine quickly, without evo-
lution of vapour or rise of temperature, forming a yellowish red-brown,
viscid mass (Zeller) ; it dissolves to of iodine, with rise of temperature,
and is converted into a dark brown-red, viscid, opaque, stinking liquid,
which, on cooling, deposits black crystalline laminae, apparently consist-
ing of iodine and cinsebene. (Hirzel.) Water shaken up with" the solu-
tion of iodine in wormseed-oil extracts from it acetic, propionic, and
hydriodic acids, together with a substance smelling like opium, probably
iodide of propyl. The solution of iodine in wormseed-oil gives off when
distilled, aqueous propionic acid, hydriodic acid, iodoform, and especially
a mobile, dark brown, peculiar-smelling oil, consisting chiefly of cinsebene-
camphor, cinsebene and cymene, together with hydriodic acid both dis-
solved and chemically combined, also hydriodate of cinsebene, and small
quantities of angelic acid and cinacrol, whilst there remains a solid, blue-
black, easily inflammable body which burns, though very slowly, with a
clear, luminous flame, and consists of cinsephene, cinsephone, and cinae-
phane. 3. With nitric acid, it acquires a reddish yellow colour (Zeller),
and when heated therewith gives off gas with violence, and is converted
into a yellow resinous mass insoluble in water (Zeller, Volkel) ; with
dilute nitric acid, it forms oxalic acid (Volkel) ; heated in small quan-
tities with nitric acid, it forms toluylic acid, a small quantity of oxalic
acid being formed only when strong nitric acid is used. (Hirzel.)
4. With oil of vitriol, it acquires a red-brown colour (Zeller), becomes
hot and viscid, and after some time gives off sulphurous acid. (Volkel.)
j. It absorbs hydrochloric acid gas, and when saturated therewith
forms a dark red oil, which on cooling deposits crystals of wormseed-oil
camphor. (Volkel, Hirzel.) 6. Heated with anhydrous phosphoric acid,
it forms a black mass, which on boiling yields as, liquid products, aqueous
propionic acid, cinaebene, cinoephene and cinncrol (Hirzel) ; it becomes


partially resinised, viscid, and is converted into cynene. (Volkel.)
7- Distilled with hydrate of potash, it yields a mobile, limpid oil having
an agreeable odour (like oil of peppermint, according to Volkel), and a
warm burning taste ; easily inflammable, burning with a clear flame,
having a sp. gr. of 0*93, consisting of an equal number of atoms of cinse-
bene, cinaebene-camphor and a compound containing C 10 H 8 0, with \ At.
propione, and boiling at 175 176'5. Hydrochloric acid gas colours
this oil red, and forms with it, shining very deliquescent needles. Oil of
vitriol renders it viscid and dark brown, and when heated with it, gives
off sulphurous acid ; nitric acid converts it into liquid volatile products
and fixed resinous products ; distilled with anhydrous phosphoric acid, it
giv r es off propionic acid, an oil consisting of 4 At. cymene, 2 At. cinsebene,
and 1 At. cinsebene-camphor., together with smaller quantities of cinse-
phene and cinacrol. (Hirzel.)

Combinations. With Hydrochloric Acid. Wormseed-oil camphor.
Obtained by passing dry hydrochloric acid gas into wormseed-oil, cooling
the saturated red oil, and pressing the separating crystalline mass between
filtering paper. Colourless slender needles. Odour aromatic, like that
of camphor ; taste mild and warming. When exposed to the air, it
deliquesces and takes up water (Volkel) ; without taking up water
(Hirzel). When heated, it melts into a nearly colourless oil, which
gives off hydrochloric acid by distillation. Deliquesces quickly when
covered with water. (Volkel, Hirzel.)

Wormseed-oil dissolves in 1000 pts. of water, readily in alcohol and
ether (Trommsdorff), in every proportion of absolute alcohol, and in an
equal quantity of alcohol of sp. gr. 0'85. (Zeller.)

Cinaephane. C 20 H 8 .

HIRZEL. (1855.) Zeitschr. J. Pharm. 1855, 163, 182.

Formation. By distilling wormseed-oil with iodine (p. 317).

Preparation. The thick brown liquid produced by dissolving iodine
in wormseed-oil is distilled, and the resulting brown oil is heated to
above 360, whereby a distillate is obtained, consisting chiefly of
cinsebene-camphor, cinsebene, cinacrol, and cymol. while a mixture of
cinsephane, cinsephene, and cinsephone remains behind. The residue
well boiled with alcohol, gives up cinsephene to that solvent, and after
the adhering alcohol has been evaporated, is itself soluble in chloroform.
On mixing this solution with 20 pts. of alcohol of sp. gr. 0'84, it
deposits a "resin, which, after washing with hot alcohol and water, is a
mixture of cinsephane and cinsephone. The latter is dissolved out by
ether, and the residual cinsephane is purified by solution in chloroform,
preparation with alcohol, and washing with ether. The cinsephone is preci-
pitated from the ethereal solution by alochol.

Properties. Very soft, loose, nearly velvet-black powder, without
taste or smell.


20 C ....
8 H ....

.... 120 ..

8 ..

.. 93-75
.. 6-25

. 93-29

C-H 8 128 .... 100-00 99-69


Decompositions and Combinations. Cinaephene, when heated, burns
away with a glimmering light, without melting or leaving any residue.
It dissolves in chloroform, but not in ether. (Hirzel.)


HIRZEL. (1855.) Zeitschr. J.Pharm. 1855, 163, 182.

Formation. By distilling wormseed-oil with iodine (p. 317).

Properties. Soft, loose, light, kerrnes-brown powder, which adheres
strongly to glass, to paper, and to the fingers ; tasteless and inodorous.
It has not been obtained quite free from iodine.

Decompositions and Combinations. When heated, it melts to a black
mass, gives off empyreumatic vapours, and leaves a light charcoal which
burns away easily and completely. When set on fire, it burns with a
yellow non-fuliginous flame, leaving a large quantity of pure charcoal.
It dissolves readily in chloroform, ether, and wormseed-oil, but is insoluble
in water, alcohol, and aqueous alkalis. (Hirzel.)

Cinajbene. C 20 H 16 .

HIRZEL. (1854.) Zeitschr. f. Pharm. 1854, 7, 67. 1855, 52; 68, 82;
147; 182.

Source. In wormseed-oil, together with cinsebene- camphor, and small
quantities of propionic acid and oxide of propyl.

Formation. By distilling wormseed-oil with anhydrous phosphoric
acid, whereby the cinsebene-camphor is dehydrated.

Preparation. By distilling wormseed-oil with anhydrous phosphoric
acid in a retort, so long as, together with aqueous products, a light oil
passes over with brisk but ultimately quiet ebullition, and till only a
small quantity of oil remains mixed with the phosphoric acid ; shaking
up the oily distillate with water and carbonate of baryta; and rectifying
it over anhydrous phosphoric acid after dehydration with chloride of

Properties. Transparent, colourless, slightly iridescent, refracting,
mobile. Sp. gr. 0*878 at 16. Boiling point 172. Odour slightly
aromatic, more like that of oil of amber when heated. Cincebene from
wormseed-oil, prepared by distilling wormseed with milk of lime, smells
like oil of lemon. Taste slightly warming, afterwards burning.


20 C ....
16 H ...

.... 120 ..
.... 16 ..

.. 88-23 ....
.. 11-77 ....

.... 88-27
... 11-71

C 20 H 16 136 .... 100-00 99-98

Isomeric with terebene. Probably identical with Volkel's cynene. (Schwanert.)


Decompositions } . Cinsabene, when set on fire, burns with a clear
flame 2. Heated with an equal volume of nitric acid of sp. gr. 1*16,
it gives off, with violent intumescence and evolution of nitrous acid,
first, water containing propionic or acetic acid, and floating thereon, a
thin colourless oil which has a fruity odour, leaves when evaporated,
flocks smelling like camphor, is very volatile, is easily set on fire, and
burns with a clear flame, and, ultimately, hydrocyanic acid with a small
quantity of bitter almond-oil, while a viscid resin remains. This resin
has a peculiar odour like anise and fennel, and yields, by renewed boiling
with nitric acid of sp gr. 1-16, a solution which, on cooling, deposits
toluylic and nitrotoluylic acids, also an undissolved viscid oil which
appears to be anisylous acid. No oxalic acid is formed. A small
quantity of cinsebene added to strong nitric acid colours it dark red ; the
mixture froths up strongly when heated, arid contains a small quantity
of oxalic acid. Cinsebene, heated with oil of vitriol, acquires a red-brown
colour. 3. Dry hydrochloric add gas colours it wine-red without
separating crystals ; on dissolving the ciuaebene thus coloured in alcoholic
potash, and adding water, a colourless oil separates, having a strong and
agreeable odour of camphor, and decomposing when heated.

Combinations. 1. With Water. Cincebene-camphor, Hydrated Cince-
bene, C 20 H 18 0*. Occurs in worm-seed-oil, together with propionic acid
and oxide of propyl, but cannot be separated in the pure state.

2. With Hydriodic Acid. Hydriodate of Cincebene, 2C 20 H 16 ,HL -
Obtained by rectifying the oil which passes over when wormseed-oil is
distilled with iodine ; collecting apart the last portion of the distillate,
extracting the cinacrol from it by repeated agitation with aqueous potash;
washing the residual oil with water, then distilling it with water, and
collecting separately the last portion of the oily distillate, which must
then be washed with water and dehydrated with chloride of calcium.

Limpid to pale yellow, tolerably viscid ; has an agreeable camphorous
peristent odour. Neutral.

40 C


60-00 ..


... 59-60

33 H


.... 33 ,
... 127 .

... 8-22
... 31-78

... 31-59

2C 20 H 16 ,HI 400 .... 100-00 99'83

It becomes reddish by exposure to the air, and is decomposed by dis-
tillation, even with water. (Hirzel.)

Cinsebene is insoluble in water, but dissolves readily in alcohol and
ether. (Hirzel.)

Cynene. C*H

VOLKEL. Ann. Pharm. 89, 358.

Formation and Preparation. Wormseed-oil is repeatedly distilled
with anhydrous phosphoric acid ; the oil, which resinises and becomes


viscid, is mixed with oil of vitriol ; and the layer of liquid which floats
oil the acid is removed, distilled with water after washing, and again per
se, after dehydration with chloride of calcium.

Properties. Limpid and mobile. Sp. gr. 0'825 at 16. Boils at
373 175. Odour peculiar, like that of wormseed ; taste faint, after-
wards burning.

>4 C


. . 88-89

.... 8874

18 H


. . ll'll


C-'H 13 162 .... 100-00 99-98

Formed from wormseed -oil, C 24 H 20 O 2 , by separation of 2 At. water. (Volkel.)
Probably identical with Hirzel's cinsebene. (Schwanert.)

Decompositions and Combinations. 1. Burns with a bright fuliginous
flame when set on fire. 2. With cold strong nitric acid, it becomes
yellowish-brown; boiled with strong nitric acid, it forms, with violent
action, a solution which deposits a heavy yellow oil when mixed with
water ; by warm dilute nitric acid it is not altered. It dissolves in
fuming oil of vitriol, forming a conjugated acid. It is insoluble in water,
easily soluble in alcohol and ether. (Volkel.)

Cin&phene. C 20 H 16 or C 10 H 32 -

HmzEf, Zeitsch. f. Pharm. 1854, 1 7, 1 82. 1855, 162, 182.

Formation. By distilling wormseed- oil with anhydrous phosphoric
acid or with iodine.

Preparation. 1. The oil which passes over on heating wormseed-oii
with anhydrous phosphoric acid, is freed from admixed aqueous products,
and the portion which goes over between 35 and 325, when it is rectified
perse, is collected and dried over chloride of calcium. 2. The brown
oil obtained by distilling wormseed-oil with iodine is rectified; the light
brown viscid residue is extracted with strong aqueous potash, washed
with water, and heated to 360 as long as oil continues to distil over ;
and this oil is freed from admixed cinacrol by agitation with warm dilute
aqueous potash, then with water, afterwards dried with chloride of
calcium, and rectified.

Properties. Transparent and colourless by transmitted light, but
exhibits an indigo-blue iridescence by reflected light ; viscid ; lighter
than water. Boils at 315 325. Nearly destitute of taste and smell.


20 C
16 H

120 ....
16 ....

88-24 ...
11-76 ...


C : H 16 136 .... 100-00 99-66

Probably isomeric with colophene. (Hirzel.)

Decompositions and Combinations. 1. When heated, it becomes
mobile and gives off vapours smelling like amber; burns with a very
smoky flame when set on fire. 2. When heated with strong sulphuric



acid, it is converted into a yellow resin, which has a peculiar musk-like
odour, and when distilled with aqueous potash, yields, with frothing, a
distillate smelling of ammonia.

Cinsephene is insoluble in water, sparingly soluble in cold alcohol,
easily in hot alcohol, ether, and volatile oils.

Cinacrol. C 26 H 18 0*.

HIRZEL. Zeitschr.f. PJiarm. 1855, 84; 98, 130.

formation. From wormseed-oil : a. by heating with iodine ; b. by
distillation with anhydrous phosphoric acid ; c. by heating with hydrate
of potash.

Preparation. Wormseed-oil is distilled with ^ \ iodine ; the mobile,
dark brown iodated oil which passes over is separated from the aqueous
distillate, and rectified per se; the nearly black heavy oil which passes
over towards the end of the distillation is collected and shaken up with
strong aqueous potash ; the potash-ley, which thereby acquires a dark
brown-yellow colour, is heated till it becomes inodorous, then distilled
with a slight excess cf dilute sulphuric acid ; and the oil which passes
over is rectified over chalk, and dehydrated by agitation with chloride of

Properties. Colourless to pale yellow; viscid. Sp.gr. 1-05 1*1 5.

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