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Quinoline AlkaloidsQuinoline AlkaloidsCinchonaCinchona Alkaloids Alkaloids
Cinchona bark contain many alkaloids the majors are:Cinchona bark contain many alkaloids the majors are:
1- Quinine and Quinidine.1- Quinine and Quinidine.
2- Cinchonine and Cinchonidine.2- Cinchonine and Cinchonidine.
Cinchona alkaloids are presentCinchona alkaloids are presentas salts with Quinic andas salts with Quinic and
Cinchotannic acids.Cinchotannic acids.
They are diacidic bases form two types of salts:They are diacidic bases form two types of salts:
1- eutral salts !"onoacidic# !less water soluble.1- eutral salts !"onoacidic# !less water soluble.
2- Acidic salts !$iacidic# water soluble.2- Acidic salts !$iacidic# water soluble.
OHHO
OH
HO COOH
Quinic acid
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%oth Quinine and Quinidine& Cinchonine and Cinchonidine%oth Quinine and Quinidine& Cinchonine and Cinchonidineare $iastereoisomers. 'ach pair differs in theare $iastereoisomers. 'ach pair differs in the
stereochemistry at C-( and C-).stereochemistry at C-( and C-).
*+C,
*,
* *
*+C,
*,
* *
89
Quinine Quinidine
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Properties:Pro
perties: QuinineQuinine is ery slihtly soluble in *is ery slihtly soluble in *22,& soluble in,& soluble in
ethanol& chloroform& ether& ben/ene and other oranicethanol& chloroform& ether& ben/ene and other oranicsolents.solents.
QuinineQuinine is ais a diacidic basediacidic base. 0t forms 2 types of sulfates:. 0t forms 2 types of sulfates:
Quinine monosulfateQuinine monosulfate !!neutralneutral andand HH22O insolubleO insoluble#.#.
Quinine bisulfateQuinine bisulfate !!acidicacidic andand HH22O solubleO soluble#.#.
QuinineQuinine !!l l -isomer# ies-isomer# ies quinidinequinidine !!d d -isomer# amon-isomer# amon
other products when warmed with ,* in amylother products when warmed with ,* in amyl
alcohol.alcohol. Quinine is leorotatory& while uinidine is de3trorotatoryQuinine is leorotatory& while uinidine is de3trorotatory ..
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Separation of the 4 AlkaloidsSe
paration of the 4 Alkaloids
Powdered Bark
- Alk . CaO + NaOH + H2O
- Reflux with benzene &
- Filtration while hot
Benene filtrate (Alkaloidal bases)
dilute H2SO4
Acidic aqueous la!er (Alkaloidal bisulphates)
pH to 6.5 with Na2CO3
Precipitate
Quinine uinidine!
cinchonine " cinchonidineHot water ! Na2CO3
Quinine NaOH, ethe#
Aqueous la!er "ther la!er
CinchonineQuinidine " Cinchonidine
$HCl PH=! Na! % &a#t. salt
$ 'ilte#
Precipitate #iltrate
Cinchonidine ta#t#ate Quinidine ta#t#ate
Aqueous solution !onosulphates)!onosulphate)
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$ests for identification$ests for identification
%&%& #luorescence test:#luorescence test:
4olution of the alkaloid in o3yenated acids !e. *4olution of the alkaloid in o3yenated acids !e. *224,4,55& *,& *,++ ororphosphoric acid#phosphoric acid# blue fluorescence !6 e with uinine and uinidine#.blue fluorescence !6 e with uinine and uinidine#.
2& $halleoquine test:2& $halleoquine test: Aueous solution of the alkaloidal salt 6 %r Aueous solution of the alkaloidal salt 6 %r 22 7*7*22, !few drops till the, !few drops till the
appearance of yellow color# 6 *appearance of yellow color# 6 *
55,*,*
emerald reenemerald reen
colorcolor
!6 e with uinine and uinidine#.!6 e with uinine and uinidine#.
+-+- 'osequin test ("r!throquinine test):'osequin test ("r!throquinine test):
Aueous solution of the alkaloidal salt 6 dil *Cl 6 %r Aueous solution of the alkaloidal salt 6 dil *Cl 6 %r 22 7*7*22, !few drops till the, !few drops till the
appearance of yellow color# 6 C*Cl appearance of yellow color# 6 C*Cl++ 6 pot. 8errocyanide 6 *6 pot. 8errocyanide 6 *55,*,* redred color in the C*Clcolor in the C*Cl++ layer !6 e with uinine and uinidine#.layer !6 e with uinine and uinidine#.
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,soquinoline Alkaloids,soquinoline Alkaloids%&%& IpecacuanhaI pecacuanha AlkaloidsAlkaloids
Occurrence:Occurrence:
,pecac,pecac is the dried roots and rhi/omes ofis the dried roots and rhi/omes of Cephalis ipecacuanhaCephalis ipecacuanha !%ra/ilian!%ra/ilian
ipecacuanha# oripecacuanha# or Cephalis acuminataCephalis acuminata !Cartaena or ;anama ipecacuanha#!Cartaena or ;anama ipecacuanha#
8am. ?#& mainly e+etinee+etine !>9- @9 ? of total!>9- @9 ? of total
alkaloids#& withalkaloids#& with cephalinecephaline andand ps!chotrineps!chotrine ..
-
.eO
'O
-
O.eO.e
HH
* e ,etine
* H Cephaline
-
.eO
HO
-
O.eO.e
H
-schot#ine
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"+etine:"+etine: 0t is0t is non phenolicnon phenolic andand le/orotator!le/orotator!..
0t contains 2 basic nitroens.0t contains 2 basic nitroens.
Cephaline:Cephaline: 0t is0t is phenolicphenolic andand le/orotator!le/orotator!..
0t0t 0i/es e+etine0i/es e+etine onon +eth!lation with (CH+eth!lation with (CH11))22 SOSO44..
Ps!chotrine:Ps!chotrine:
,ccurs as yellow prisms.,ccurs as yellow prisms.
0t is0t is phenolicphenolic and iesand ies cephalinecephaline on reductionon reduction..
0t0t 0i/es e+etine0i/es e+etine onon reduction followed b! +eth!lationreduction followed b! +eth!lation..
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,solation of ,peca alkaloids:,solation of ,peca alkaloids:Powdered root and rhio+e- "xt. alcohol,#on$., lead acetate.
- Filtration
#iltrate 'esidue Non$alkaloidal sub.
- "%ap., dil. HCl & Filtration
Alkaloidal bases and salts
#iltrate (Alkaloidal HCl salts)
- Alk. with NaOH & "xt. with ethe#
"ther la!er
,etine
(-henolic alkaloids)
- H#l !Alkaloidal alt'
- Alk. (H)*H "xt. ethe#
Aqueous la!er "ther la!er
(-schot#ine) (Cephaline)
Aqalk solution
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$ests for identification of ,peca alkaloids:$ests for identification of ,peca alkaloids:
Alkaloidal solution in *Cl 6 Alkaloidal solution in *Cl 6 Ca h!pochloriteCa h!pochlorite
oran0eoran0e color.color.
"+etine"+etine andand cephalinecephaline 66 #roehd3s#roehd3s reaent:reaent: dirt! 0reendirt! 0reen color !thecolor !the
color with emetine fades by addition of *Cl#.color with emetine fades by addition of *Cl#.
Ps!chotrinePs!chotrine 66 #roehd3s#roehd3s reaent:reaent: pale 0reenpale 0reen color.color.
CephalineCephaline andand ps!chotrineps!chotrine 66 p p-nitrodia/oben/ene-nitrodia/oben/ene dye soluble indye soluble in
a,*a,* purplepurple color.color.
Ps!chotrinePs!chotrine 6 conc. *6 conc. *224,4,55 66 *,*,++ cherr! redcherr! red color color ..
EmetineEmetine + Liebermann's reagent+ Liebermann's reagent blackblack color.color.
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*ses:*ses:
"+etine"+etine andand cephaelinecephaeline haehae antitu+our antitu+our andand anti/iralanti/iral actiity& but are too to3ic for therapeutic use.actiity& but are too to3ic for therapeutic use.
"+etine and ps!chotrine"+etine and ps!chotrine are mainly used asare mainly used as e+etice+etic
dru0sdru0s
The crude dru is used asThe crude dru is used as epectorantepectorant !due to its saponin!due to its saponincontent# .content# .
"+etine"+etine *Cl and $ehydroemetine !$*'# hae an*Cl and $ehydroemetine !$*'# hae an
antia+oebic effect5antia+oebic effect5 and are used for the treatment ofand are used for the treatment of
amoebic dysentry andamoebic dysentry and Fasciola.Fasciola. 0peca alkaloids are0peca alkaloids are diaphoreticdiaphoretic& alone or in combination with& alone or in combination with
opium !e..opium !e.. 6o/er3s6o/er3s powder powder #.#.
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2& Curare Alkaloids2& Curare Alkaloids Occurrence:Occurrence: Curare or 4outh American arrow poison is the dried crude e3tract& obtainedCurare or 4outh American arrow poison is the dried crude e3tract& obtained
mainly frommainly from ChondrodendronChondrodendron tomentosumtomentosum !"enispermaceae# and certain!"enispermaceae# and certain44trychnostrychnos species& !oaniaceae#.species& !oaniaceae#.
Curare contains se/eral alkaloids (4&78)5 the +ost i+portant isCurare contains se/eral alkaloids (4&78)5 the +ost i+portant is d d &tubocurarine&tubocurarine
-
OH
.eO
-
H
H
.e
O.e
O
OH
O
.e
+.e
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Properties:Properties: d d &tubocurarine&tubocurarine !5ary alkaloid# is!5ary alkaloid# is freel! soluble in Hfreel! soluble in H22OO.. 0t is a0t is a phenolicphenolic
detrorotator!detrorotator! alkaloid. 0t is aalkaloid. 0t is a bisbis&ben!ltetrah!droisoquinoline&ben!ltetrah!droisoquinoline
alkaloidalkaloid
$ests:$ests: 4aturated aueous solution4aturated aueous solution ++ 8eCl+8eCl+ faint reen colorfaint reen color reen color.reen color.
4olution of the alkaloidal *C1 6 a2C, +4olution of the alkaloidal *C1 6 a2C, + yellow brown precipitate. yellow brown precipitate.
*ses:*ses: $ubocurarine chloride$ubocurarine chloride is mainly used by i.m. or i.. routes asis mainly used by i.m. or i.. routes as
skeletal +uscle relaantskeletal +uscle relaant.. 0t is used to0t is used to control and reduce con/ulsions of str!chninecontrol and reduce con/ulsions of str!chnine
poisonin and ofpoisonin and of tetanustetanus
0t is used as a dianostic aid in0t is used as a dianostic aid in +!asthenia 0ra/is+!asthenia 0ra/is..