43
Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
Basima A. A. Saleem
Abstract
A spectrophotometric method is proposed for the determination of some drugs containing
amino group such as mesalazine, metoclopramide and dopamine in pharmaceutical
formulations. It was simple, precise, accurate, rapid, and based on the oxidation of each drug
with chromate as an oxidizing agent in the presence of 1N hydrochloric acid. Then indigo
carmine is reacted with residual chromate in the presence of a catalysis factor (sodium
oxalate). Increasing in absorbance's value of the color system is proportional to the amount of
the three drugs which is measured at the selected wavelength of 610 nm.
The proposed method is obeying Beer's law in the ranges of (1-40, 2-44 and 2-52) ppm for
the concentration of mesalazine, metoclopramide and dopamine respectively. Molar
absorptivity was 0.191×10
4
, 0.449×10
4
and 0.191×10
4
L.mol
-1
.cm
-1
mesalazine,
metoclopramide and dopamine respectively. While, Sandell's sensitivity index of 0.0806,
0.0667 and 0.0806 μg.cm
-2
mesalazine, metoclopramide and dopamine respectively.
The proposed spectrophotometric method has a good recovery when it is applied for the
determination of the three drugs in pure form and pharmaceutical doses.
Keywords: Spectrophotometric oxidation-reduction reaction, Mesalazine, Metoclopramide,
Dopamine
1. Introduction
Mesalazine and metoclopramide are used for treating of digestive system diseases, drugs
containing amino group as well as dopamine Scheme 1. Metoclopramide is one of the
medications groups which is known as dopamine-receptor antagonists, therefore these drugs
have been chosen in this study.
Mesalazine (MEZ), also named as 5-amino-2-hydroxybenzoic acid, is white color for
powder and crystals [1]. it is relatively insoluble in some organic solvents like ether and
chloroform, while it is solubility increased in a diluted solution of bases and acids [2]. Some
biological terms like enzymes are inhibited to be produced by MEZ, such as synthetase and
cyclo-oxygenase [3]. also, MEZ played an important role as an activating factor of the
Ibn Al Haitham Journal for Pure and Applied Science
Journal homepage: http://jih.uobaghdad.edu.iq/index.php/j/index
Doi:10.30526/32.3.2281
Spectrophotometric Determination of some Drugs using Oxidation
Reduction Reactions
Department of Chemistry, College of Science, University of Mosul
basmasaleem@yahoo.com
Article history: Received 24 February 2019, Accepted 11 June 2019, Publish September,
2019.
basmasaleem@yahoo.com
44
Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
platelet. MEZ as an anti-inflammatory drug is used for treating the common disease of
inflammatory bowel and Crohn’s disease [4, 5].
Metoclopramide (MET) is a medication chemically known as 4-amino-5-chloro-N-(2-
diethylaminoethyl)-2-methoxybenzamide [1]. and used for stomach and esophageal problems.
Also MET is used to treat hyperemesis gravidarum by pregnancy's women as a second choice.
There is a relation between MET and DOP, MET belongs to medications group which is
known as dopamine-receptor antagonists. People with Parkinson's disease must be noticed
closely when they are used the medication DOP as an antagonist to treat the emesis. Patients
are not recommended to take MET if they have been taken antipsychotics drugs [6,7].
Dopamine (DOP) chemically named as 4-(2-Aminoethyl) benzene-1,2-diol[1]. DOP is
synthesized in the brain, plants and most animals. It is a chemical send signal to nerve cells
when it is released by other nerve cells, dopamine's pathways in the brain are controlling the
release of various hormones. Any dysfunctions of the dopamine system are associated with
important diseases in the nervous system such as Parkinson's disease; it is causing motor
impairment and tremor. The important function of dopamine is a neurotransmitter in the
brain. Other functions increase the excretion of sodium and output urine from kidneys. It
reduces insulin production as well as reduces gastrointestinal motility, protects intestinal
mucosa, reduces the activity of lymphocytes in the pancreas and in both digestive system and
immune system respectively [8-11].
HO
NH2
OHO
Mesalazine
153.14 g/mol
NH2HO
HO
Dopamine
C8H11NO2
153.18 g/mol
NH
NCl
NH2
O
O
Metoclopramide
C14H22ClN3O2
299.80 g/mol
Scheme 1. Chemical structure of MEZ, MET and DOP.
Several techniques, including spectral methods, were used to estimate three drugs as
documented in the literature. MEZ was evaluated in its pure form and in its pharmaceutical
preparations using various organic reagents such as 1, 2-Naphthoquinone-p-sulphonate, 4-
dimethylaminocinnamaldehyde [12]. o-chloranil [13]. 1, 5-diphenylcarbazide [14]. N-(1-
naphthyl) ethylenediamine and 8-hydroxyquinoline [15]. Also, inorganic reagents are used to
determine MEZ like sodium nitroprusside with hydroxylamine HCl [16]. and ferric nitrate [2].
Another method depends on ultra violet region to determine MEZ [17,18].
Spectrophotometric methods are also used for the determination of MET with its
degradation products [19]. as well; others applied for the determination of MET in bulk and
pharmaceutical preparations [20-22]. MET has been determined in pharmaceuticals and
spiked human urine using diazotization reaction [23-26]. Sequential injection is used for
spectrophotometric determination of MET [27]. Development and validation of UV-
spectroscopic method are used for assaying of MET in bulk and injectable dosage form [28].
Batch and cloud point extraction spectrophotometric is used for the determination of DOP
[29]. A spectrophotometric method is used for determination of DOP in various samples such
as bulk and injectable forms [30, 31]. Other used charge transfer reaction with bromanil to
determine DOP [32]. Or, we used a spectrophotometric evaluation of DOP and progesterone
https://en.wikipedia.org/wiki/Hyperemesis_gravidarum
45
Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
in breast cancer serum [33]. Standard addition methods are used for determination of DOP
and levodopa in tablets and ampoules [34].
DOP can be determined spectrophotometrically in biological and pharmaceutical samples
[35]. Flow injection analysis has been used for the determination of methyldopa and DOP in
pharmaceutical preparations [36]. also, DOP was determined in various samples such as
pharmaceutical, banana, urine and serum samples by potassium ferricyanide-Fe (III)[37].
Another method is used for the determination of DOP in the microliter scale using the
microfluidic system based on polymeric technology [38].
The organic reagent which used in this work is named indigo carmine Scheme 2. indigo
carmine (INC) also named as 5,5′-indigodisulfonic acid disodium salt. It is an oxidation-
reduction indicator, prepared by sulphonation process of indigo. INC is rapidly dissolved in
water, and it is safe to use as a colorant of food as well as a dye in the industry of capsules
[39].
N
N
O
O H
H
S
O
O
O-
S
O
O
-O
Na+
Na+
Indigo Carmine
M.wt = 466.36 g/mol
C16H8N2Na2O8S2
Scheme 2. The chemical structure of INC.
2. Experimental
2.1 Equipment
Double beam JascoV-630-Uv-visible spectrophotometer with a pair of a plastic 1-cm
matched cells were used for measuring absorbance while a of HANNA instrument pH 211
microprocessor pH meter was used for pH measurements.
2.2 Drug Stock Solution, (1000 µg/ml)
0.1 g of MEZ was weighed and dissolved in 10 ml of ethanol absolute and diluted with
distilled water using a 100 ml volumetric flask. While (MET & DOP) was prepared by
dissolving the same weight (0.1g) of pure dopamine hydrochloride (Fluka) or metoclopramide
(SDI) in distilled water then diluted it to the mark with the same solvent in 100 ml volumetric
flask. Standard solutions were prepared by suitable dilution of the stock standard solution.
2.3 Chromate Ion Solution, (8.6×10
-4
M) Solution
0.0167 g of potassium chromate (Fluka) was dissolved in distilled water. Then the final
volume brings to 100 ml in an amber color volumetric flask, which is being stable more than
1 month [24].
2.4 INC solution, (1×10
-3
M)
0.1165 g of indigo carmine dye (BDH) was weighed, dissolved then completed by distilled
water to a 250 ml in a dark volumetric flask in order to be stable for 3 days.
https://en.wikipedia.org/wiki/Sulfonation
https://en.wikipedia.org/wiki/Indigo_dye
https://en.wikipedia.org/wiki/Food_coloring
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Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
2.5 Catalyst solution of sodium oxalate, (0. 1 M)
1.34 g of sodium oxalate (Fluka) was dissolved in distilled water to prepare 0.1 M of this
solution which is diluted by distilled water using a 100 ml dark volumetric flask.
2.6 Hydrochloric Acid Solution, (1N).
A suitable appropriate dilution of (21.85 ml) of concentrated hydrochloric acid
(density=1.16) with distilled water in 250 ml volumetric flask to prepare 1 N of HCl.
2.7 Pharmaceutical Formulations (tablet)
Ten tablets of pharmaceutical formulations for MEZ, MET and DOP were crushed and
mixed well then, an equivalent weighed to 0.01 g of drugs were dissolved, filtered then
diluted to 100 ml with a clean and dry volumetric flask.
2.8 Pharmaceutical Preparation (Ampoule)
Plemazol, 10mg/2ml (SDI Co. Iraq) 2 ml ampoules each containing 0.01 g of MCP were
transferred to 100 ml volumetric flasks and completed the volume with distilled water.
Dopamine hydrochloride ampoule (200mg/5ml): one ampoule of dopamine hydrochloride
was diluted to 100 ml in a volumetric flask with distilled water. Then 5ml from the above
solution was diluted to 100 ml in a volumetric flask with distilled water to obtain (100 ppm).
3. Results and Discussion
Different analytical parameters which were affected on the optimum conditions of the
color development for 100 μg of each drug in 25 ml as a final volume, then the absorbance
intensity was measured at 610 nm and optimum pH from 3.2 to 3.4 for the proposed method.
3.1 Effect of Type and Quantity of Acid
Various quantities (0.1-2.0 ml) of an acids such as (HCl, H2SO4, HNO3, and CH3COOH),
were used to determine the optimum pH for the oxidation-reduction reaction between chromium
ion and drugs, HCl is considered to be optimum in this study because of the best absorbance
values so that, (0.1-2.0 ml) of 1M hydrochloric acid was studied. Figure 1. shows that use 1 ml
of hydrochloric acid (1 M) was optimum due to a high value of absorbance and the more stable
colored dye. This scale was adopted in subsequent experiments.
Figure 1. Study the effect of hydrochloric acid.
0
0.2
0.4
0.6
0 0.25 0.5 0.75 1 1.25 1.5 1.75 2 2.25 2.5 2.75 3
A
b
so
rb
a
n
ce
Hydrochloric acid amount added, ml
Mesalazine Metoclopramide Dopamine
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Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
3.2 Study the Effect of Catalyst
Sodium oxalate was used as a promoting the activation of Cr (VI) oxidation's system
[40]. Thus, different quantities of (0.1 M) C2O4
2-
solution (1.0-3.0) ml were tested with (100)
µg of drugs in final volume of 25ml. It is observed from Figure 2. that using (2.0) ml of
C2O4
2-
solution was optimum amount because it gives the best stability and
absorbance, therefore, it used in subsequent experiments.
Figure 2. Effect of catalyst.
3.3 Study the Amount of Chromate Ion
To choose the suitable amount of chromate (VI) which oxidized the drugs, various
amounts (0.5-3.0) mL of (8.6×10
-4
M) chromate and (100-1000) µg of drugs solution in final
volume 25 ml were studied. Resulted from this study that 1.5 ml of Cr (VI) was considered to
be optimum because the higher value of determination coefficient (0.9909, 0.9947 and
0.9966) for MEZ, MET and DOP respectively, for this reason it selected for the subsequent
experiments
3.4 Study the Effect of Reagent's Amount
The addition of indigo carmine as a reagent on the reaction mixture to produce the bluish
color. This was investigated by different amount of (0.5-2.0) ml 1.0×10
-3
M of the dye, the
experimental results indicated that (1.0) ml of indigo carmine reagent was optimum volume
(determination coefficient (R
2
) 0.9935, 0.9954 and 0.9964), for MEZ, MET and DOP
respectively, and fixed for the subsequent experiments
3.5 Study the Effect of Addition's Order
Different orders were studied to check the best orders of addition. Table 1. indicates that
the first order for each drug is considered to be optimum and selected for the subsequent
experiments for MEZ, MET and DOP because it gave the highest absorbance value, that
means the addition of oxidant agent to the drugs must followed by catalyst in presence of acid
medium to complete the oxidation process, then, the reagent must be added at last.
0
0.2
0.4
0.6
0 0.5 1 1.5 2 2.5 3 3.5
A
b
so
rb
a
n
ce
Amount of oxalate ion, mL
Mesalazine Metoclopramide Dopamine
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Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
Table 1. Order effect of addition.
Reaction components Order number Absorbance
MEZ
D + O + C+ H + INC I 0.334
D + H + O + C + INC III 0.281
D + INC + O + H + C IV 0.089
D + C + O + H + INC II 0.262
MET
D + O + C+ H + INC I 0.361
D + H + O + C + INC III 0.296
D + INC + O + H + C IV 0.110
D + C + O + H + INC II 0.271
DOP
D + O + C+ H + INC I 0.390
D + H + O + C + INC III 0.287
D + INC + O + H + C IV 0.121
D + C + O + H + INC II 0.298
D= MEZ or MET or DOP, O=Oxidant, H=Hydrochloric acid, INC=Indigo carmine, C=Catalyst.
3.6 Study the Stability Time
The intensity of the absorbance for various quantities of MEZ, MET and DOP at 610 nm in
the reaction mixture was measured at various time intervals. Figure 3. shows the absorbance
when it is measured immediately as well as after two hours is seemly to be constant.
Figure 3. Study the stability of the resulting dye.
3.7 The Final Absorption Spectrum and the Calibration Graph of the Three Drugs
Drugs (MEZ, MET and DOP) were treated according to the optimum conditions, the final
spectrum and calibration are shown in Figure 4,5. While Table 2. Indicates some analytical
variables of the present method. A linear calibration graph was measured at 610 nm are obtained
over the concentrations (1-40, 2-44 and 2-52) ppm for MEZ, MET, and DOP respectively. Molar
absorptivity of 0.191×10
4
; 0.449×10
4
and 0.191×10
4
L. mol
-1
.cm
-1
for MEZ, MET, and DOP
respectively, and Sandell's index sensitivity 0.0806; 0.0667 and 0.0806 µg.cm
-2
for MEZ, MET,
and DOP respectively.
0.25
0.35
0.45
0 20 40 60 80 100 120 140
A
b
so
rb
a
n
ce
Measuring time (min.)
100 µg of MEZ
100 µg of MET
100 µg of DOP
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Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
Figure 4. Final absorption spectra of 100 μg of (a) MEZ, (b) MET and (c) DOP/25 ml measured against a
reagent blank (d) blank against distilled water.
Figure 5. Calibration's graph of drugs (MEZ, MET and DOP).
Table 2. Analytical parameters of a proposed method.
Values Analytical variables
0.191×10
4
MEZ; 0.449×10
4
MET; 0.191×10
4
DOP Molar absorptivity
(L.mol
-1
.cm
-1
)
120.0 Color's stability (minutes)
0.0806 MEZ; 0.00667MET; 0.0806DOP Sandell's sensitivity
y = 0.0005x + 0.2754 MEZ;
y = 0.0006x + 0.306 MET;
y = 0.0005x + 0.334 DOP
Regretion equation
0.9974 MEZ; 0.9992 MET; 0.9998 DOP Coefficint of determination
1 : 1 Nature of the resulted dye
3.8 Method's Accuracy and its Precision
Average of five determinations of MEZ, Met and DOP were determined at various
quantities (100, 300 and 500) μg/25ml for each one to check and test the accuracy as well as
the precision for the calibration curve. The results are tabulated in Table 3. Are reliable.
y = 0.0005x + 0.2754
R² = 0.9974
y = 0.0006x + 0.306
R² = 0.9992
y = 0.0005x + 0.3343
R² = 0.9998
0.1
0.3
0.5
0.7
0.9
1.1
0 200 400 600 800 1000 1200 1400
A
b
so
rb
a
n
ce
Drugs, µg/25 ml
MEZ MET DOP
b
c
d
a
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Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
Table 3. Accuracy and precision.
Quantity of MEZ measured, μg/25ml Recovery %* RSD, %*
100.0 99.74 ±0.4082
300.0 99.59 ±0.3247
500.0 99.32 ±0.2698
Quantity of MET measured, μg/25ml Recovery %* RSD, %*
100.0 100.54 ±0.5290
300.0 100.21 ±0.2901
500.0 100.36 ±0.2895
Quantity of DOP measured, μg/25ml R, %* RSD, %*
100.0 99.70 ±0.4748
300.0 100.23 ±0.3729
500.0 99.81 ±0.2895
* Average for 5 measurements.
3.9 Mole Ratio
Continuous variations (Job's method) have been used for the determination the reaction ratio
of the three drugs with chromate. The experimental results indicated that 1:1 belong to ratios of
MEZ, MET and DOP to chromate respectively. Depending on this ratio, the reaction's
mechanism is suggested as below Scheme 3. [44,45].
+ CrO4-2 Cr
+3 + 2H2O+
2H+
OH
NO2
OH O
OH
H2N
OH O
NH2HO
HO
Dopamine
Metoclopramide
NH
NCl
NH2
O
O + CrO4
-2 +
+ CrO4
-2
NH
NCl
O2N
O
O
NO2HO
HO
Cr+3 + 2H2O
Cr+3 + 2H2O+
2H+
2H+
Scheme 3. Oxidation of MEZ, MET and DOP with Cr (VI).
The probable reaction mechanism Scheme 4. Has been suggested between the oxidizing
agent (chromate VI) and the reagent (indigo carmine dye) in the presence of catalyst agent
(sodium oxalate) in an aqueous solution of hydrochloric acid [41]. as follows:
N
H
H
N
O
O
NaO3S
SO3Na
N
H
H
N
OH
OH
NaO3S
SO3Na
N
H
H
N
OH
OH
NaO3S
SO3NaN
H
H
N
O
O
NaO3S
SO3Na
2H+
+2Cr+3+H2O
2Cr+6
+ 2e-
+ Na2C2O4
Scheme 4. Mechanism between chromate VI and indigo carmine dye.
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Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
3.10 Study the Effect of Interferences
To study the selectivity and efficiency of the present method, the effect of some foreign
materials that are usually present in dosage forms (gum acacia, lactose, menthol, starch and
glucose) were added in different amounts (100, 500, 1000) to (100) μg of drugs/25 ml. There
is no effect of foreign substances in the proposed method as it was obtained from Table 4.
Table 4. Effect of interferences.
Recovery (%)
Drugs, μg MEZ, 100 μg MET, 100 μg DOP, 100 μg
Interferences, μg 100 500 1000 100 500 1000 100 500 1000
Acacia 99.70 99.40 99.10 99.72 99.73 100.27 98.97 98.73 98.50
Glucose 100.29 100.59 99.70 100.28 100.54 100.82 99.74 99.48 99.23
Lactose 100.59 99.70 100.29 99.44 99.73 99.72 100.77 100.25 100.26
Menthol 100.30 100.90 99.40 99.17 99.45 98.89 100.25 100.51 100.26
Starch 100.60 100.59 99.69 100.28 100.27 100.55 100.52 100.51 100.77
3.11 Application of the Proposed Method
The experimental results in Table 5. indicate that a good value of recovery, relative error
as well as the measured quantity of each drug when the present method applied on the
pharmaceutical preparations for MEZ, MET and DOP.
Table 5. Application of the method.
R.E
*
, % R
*
, % µg MEZ
measured/25ml
µg MEZ
present/25ml
MEZ
-0.2600 99.74 199.48 200 Pentasa tablet, 500 mg (Ferring,
Germany) -0.4150 99.58 398.34 400
-0.5183 99.48 596.89 600
-1.0450 98.95 197.91 200 Awasalazine tablet, 400 mg,
(Awamedica, Iraq) -0.8325 99.16 396.67 400
-0.6916 99.31 595.85 600
R.E
*
, % R
*
, % µg MET
measured/25ml
µg MET
present/25ml
MET
-0.4950 99.50 199.01 200 Plemazol, 10mg/2ml (SDI Co.
Iraq) -0.1975 99.80 399.21 400
-0.3283 99.67 598.03 600
-1.235 98.76 197.53 200 Meclodin, 10mg (CID Co. Egypt)
-1.3775 98.62 394.49 400
-1.4783 98.52 591.13 600
R.E
*
, % R
*
, % µg DOP
measured/25ml
µg DOP
present/25ml
DOP
-1.3500 99.32 198.64 200 Dopamine hydrochloride (200
mg/5 mL) miser. Co Egypt -1.6400 99.63 398.54 400
-1.5466 99.53 597.20 600
-0.6800 98.65 197.30 200 Dopamine hydrochloride
injections (Biologici Italy Lab.,
Novate, Milano - Italy): 200 mg/5
mL)
-0.3650 98.36 393.44 400
-0.4666 98.45 590.72 600
* Average of five determinations.
Table 6. Shows the calculated value of t-test at the 95% confidence level for five degrees
of freedom [42]. Did not exceed the theoretical values (t-tabulated is 4.95) when the present
method is compared with literature methods [43, 21, 30].
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Ibn Al-Haitham Jour. for Pure & Appl. Sci. 32 (3) 2019
Table 6. T-test values of MEZ, MET and DOP.
Pharmaceutical preperations Values of t-test
Pentasa tablet, 500 mg (Ferring, Germany) ± 1.8185
Plemazol, 10mg/2ml (SDI Co. Iraq) ± 1.1821
Dopamine hydrochloride injections (Biologici Italy Lab., Novate,
Milano - Italy): 200 mg/5 mL)
± 0.6469
3.12 The Comparison of the Proposed Method with Literature
Several analytical variables those have been explained in Table 7. shows the comparison
between the proposed and some methods in the literature.
Table 7. Proposed and literature method's comparison.
methods in Literature Present method Analytical variables
DOP [30] MET [21] MEZ [40]
Complex formation azo coupling
reaction
Oxidative
coupling
Oxidation -
reduction
Reaction
470 459 530 610 λmax (nm)
DCQ Orcinol Pyrocatechol Indigo Carmin Reagent
4-45 0.6-12 0.4-10 1-40 MEZ;
2-44 MET;
2-52 DOP
Beer’s law range (µg.
mL
-1
)
1938.76 19044 3685 1900 MEZ;
4490 MET;
1900 DOP
Molar absorptivity
(L.mol
-1
.cm
-1
)
--------- NaOH H2SO4 HCl Medium
------------ 24 hrs. 65.0 120.0 Color's stability
(minutes)
1: 4 ------------ 1: 1 1: 1 Nature of the resulted
dye
Bulk and Injectable
Forms
Pharmaceutical
preparation
Pharmaceutical
preparation
Pharmaceutical
formulation
Method's application
DCQ: 2,6-dichloroquinone 4-chloroimide.
The results in Table 7. Showed that the present method is somewhat sensitive to apply
for the pharmaceutical preparations of each drug (MEZ, MET and DOP).
4. Conclusion
In this work, a spectrophotometric method was proposed which is described as an accurate,
simple and fast. It was used to estimate three drugs containing the active amino group (MEZ,
MET and DOP) using oxidation-reduction reaction. This method is obeying Beer's law in the
ranges of 1-40, 2-44 and 2-52 ppm for the concentration of MEZ, MET and DOP
respectively. Molar absorptivity was 0.2×10
4
, 0.5×10
4
and 0.2×10
4
L.mol
-1
.cm
-1
MEZ, MET
and DOP respectively. The proposed method was applied successfully to the determination of
those three drugs in pure and their pharmaceutical preparations.
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