EXPERIMEANT 1

ANALYSIS OF ASPIRIN IN COMMERCIAL APC TABLET USING FTIR

SPECTROSCOPY

OBJECTIVES
To determine the aspirin (acetylsalicylic acid), phenacetin and caffeine
content in APC tablet
To understand the spectrum obtained from FTIR
INTRODUCTION
Aspirin is among the most fascinating and a versatile drug known to
medicine and it is among the oldest. The first known use of an aspirin-like
preparation can be traced to ancient Greece and Rome. Salicigen, an extract
of willow and poplar bark, has been used as a pain reliever (analgesic) for
centuries. In the middle of the last century it was found that
salicigen is a glycoside formed from a molecule of salicylic acid and a sugar
molecule. Salicylic acid is easily synthesized on a large scale by heating
sodium phenoxide with carbon dioxide at 150C under slight pressure (the
Kolbe synthesis):

Unfortunately, however, salicylic acid attacks the mucous membranes
of the mouth and esophagus and causes gastric pain that may be worse
than the discomfort it was meant to cure. Felix Hoffmann, a chemist for
Friedrich Bayer, a German dye company, reasoned that the corrosive
nature of salicylic acid could be altered by addition of an acetyl group; and
in 1893 the Bayer Company obtained a patent on acetylsalicylic acid,
despite the fact that it had been synthesized some 40 years previously by
Charles Gerhardt. Bayer coined the name Aspirin for their new product to
reflect its acetyl nature and its natural occurrence in the Spiraea plant. Over
the years the company has allowed the term aspirin to fall into the public
domain so that it is no longer capitalized. In 1904, the head of Bayer, Carl
Duisberg, decided to emulate John D. Rockefeller's Standard Oil Company
and formed an interessen gemeinschaft (IG, a cartel) of the dye
industry (Farbenindustrie). This cartel completely dominated the world dye
industry before World War I, and it continued to prosper between the wars,
even though some of their assets were seized and sold after World War I.
After World War I, an American company, Sterling Drug, bought the rights to
aspirin. The company's Glenbrook Laboratories division still is the major
manufacturer of aspirin in the United States (Bayer Aspirin). Because of
their involvement at Auschwitz, the top management of IG Farbenindustrie
was tried and convicted at the Nuremberg trials after World War II, and the
cartel broken into three large branches, Bayer, Hoechst, and BASF
(Badische Anilin and Sodafabrik), each of which now does more
business than DuPont, the largest American chemical company. By law, all
drugs sold in the United States must meet purity standards set by the Food
and Drug Administration, so all aspirin is essentially the same. Each 5
grain tablet contains 0.325 g of acetylsalicylic acid held together with a
binder. The remarkable difference in price for aspirin is primarily a reflection
of the advertising budget of the company that sells it. Aspirin is an
analgesic (painkiller), an antipyretic (fever reducer), and an anti-
inflammatory agent. It is the premier drug for reducing fever, a role for
which it is uniquely suited. As an anti-inflammatory, it has become the
most widely effective treatment for arthritis. Patients suffering from arthritis
must take so much aspirin (up to four grams per day) that gastric problems
may result. For this reason, aspirin is often combined with a buffering agent.
Buffering is an example of such a preparation. The ability of aspirin to
diminish inflammation is apparently due to its inhibition of the synthesis of
prostaglandins, a group of C-20 molecules that enhance inflammation.
Aspirin alters the oxygenise activity of prostaglandin synthesise by moving
the acetyl group to a terminal amine group of the enzyme. If aspirin were a
new invention, the U.S. Food and Drug Administration (FDA) would place
many hurdles in the path of its approval. It has been implicated, for example,
in Reyes syndrome, a brain disorder that strikes children and young people
under 18. It has an effect on platelets, which play a vital role in blood
clotting. In newborn babies and their mothers, aspirin can lead to
uncontrolled bleeding and problems of circulation for the baby-even
brain haemorrhage in extreme cases. This same effect can be turned into
an advantage, however. Heart specialists urge potential stroke victims to
take aspirin regularly to inhibit clotting in their arteries, and it has recently
been shown that one-half tablet per day will help prevent heart attacks in
healthy men. Aspirin is found in more than 100 common medications,
including AlkaSeltzer, Anacin ("contains the pain reliever doctors recommend
most"), APC, Coricidin, Excedrin, Midol, and Vanquish. Despite its side
effects, aspirin remains the safest, cheapest, and most effective non-
prescription drug.

INSTRUMENTATION
1. Instrument model : Perkin Elmer-Spectrum One (FTIR)
2. Serial no : 55705
3. Location : 306

SOLID SAMPLE PREPARATION
1. Mixture of sample and KBr
a) The agate mortar and pestle was removed from the desiccators.
b) 0.001 g of sample was grinded in agate mortar into powder.
c) 0.080 g of KBr was added into the sample powder and was
mixed using the pestle.
d) The mixture in the center of the mortar was scrapped and
heaped and was grind again for one minute. The remaining KBr
was returned into the desiccators after use.

2. KBr pellets
a) One fourth of the KBr mixture was transferred into the collar of
the handpress. The anvil was placed along with the longer die
pin, allowing it comes into contact with the samples.
b) The die set was carefully lifted by holding the lower anvil. The
collar was ensured to stay in place.
c) The handle of the handpress was opened slowly and the die set
was inserted into the handpress. The handle was closed.
d) The dial pressure was rotated until the upper ram of the
handpress slightly touches the upper anvil on the die assembly.
e) The unit was tilted back in order to hold the die set from falling
off. The handle was opened.
f) The pressure dial was rotated clockwise in one half turn.
g) The mixture was slowly compressed while closing the handle in
two minutes. The unit was tilted back, the handle was opened
and the die set was removed from the unit carefully. The pallet
was weighed and inspected.




RESULT AND DISCUSSION
1) Table for spectrum :
Frequency Range (cm
-1
) Intensity Type of Bonds Compound Types
1500-1400 Variable C=C stretching Aromatic rings
3300-2500 Medium O-H stretching Carboxylic acids
1300-1050 Strong C-O stretching Carboxylic acids, Esters
1760-1690 Strong C=O stretching Carboxylic acids, ester

The new method has been designed for the quantitative determination of
Aspirin, Phenacetin, Caffeine and their mixtures in the commercial
preparations. The quantitative determination methods for the mentioned
compounds depend on time consuming extractions. In this research FTIR
spectrometer has been used by taking the integrals of a characteristic signal
of each compound and comparing them with the integral intensity of a
standard compound.
From the analysis of aspirin by using FTIR spectroscopy, the contents of
aspirin in commercial APC tablet were determined to be 87.65 %. This is due
to the fact that sample pellet is fully transparent and nicely round shaped,
yet a little bit thick which affect the reading of FTIR spectroscopy. To reduce
the error, the amount of sample use during making the pellet must be
ensured not in excess amount and we must compress the pallet twice. First
with pressure up to 7000 psi then was left to rest for two minutes before it
was compressed again to 8000 psi and let to rest for a minute before
released from the die pin and extracted. Based on the spectrum from our
group analysis, the functional group that were presents in the aspirin are
C=C stretching (aromatic rings) in range of 1500-1400 cm
-1
,O-H stretching
(carboxylic acids) in range of 3300-2500 cm
-1
with its characteristic which is
medium and broader band, C-O stretching (carboxylic acids, esters) in range
1300-1050 cm
-1
, which carry the characteristic of strong radiation and C=O
stretching (carboxylic acids, esters) in range 1760-1690 cm
-1
. Based on the
other group spectrum, the contents of aspirin in APC tablet were determined
are slightly low to us. It is because the sample pellets for the other group is
thicker and encounter slight cracks due to improper compressing method,
thus affecting the reading for aspirin using FTIR spectroscopy. In the other
group spectrum, their spectrum was nearly similar to us, but there are
several additional peaks on their spectrum at 803.84cm
-1
, 1419.63 cm
-1
,
3589.72 cm
-1
, and 3619.59 cm
-1
. Those peaks were shown in spectrum
because during preparation of sample pellet, there are some contaminants
mixing with the samples, thus as the sample was analyze on FTIR
spectroscopy, the functional group of contaminants also shown in spectrum.
In order to prevent the contaminants from mix with sample, all the
apparatus must be cleaned first before experimental procedure. The results
obtained with this method show superiority to those obtained with
conventional methods.

CONCLUSIONS
The functional groups that present in aspirin are were C=C stretching
(aromatic rings) in range of 1500-1400 cm
-1
, O-H stretching (carboxylic
acids), C-O stretching (carboxylic acids, esters) and C=O stretching
(carboxylic acids, esters). It is clear that FT-IR spectrometry is capable of
direct determination of Acetylsalicylic acid. With the commercial software,
the method proposed is simple, precise and not time-consuming compared to
the chromatographic methods that exist in literature. Quantification could
be done in about 5-10 minutes, including sample preparation and spectral
acquisition.

REFERENCES
1. Andrei A. B, en el. FT-IR Spectrophotometric analysis of acetylsalicylic
acid and its pharmaceutical formulations. July 5,2006. University of
Bucharest, 92-96, Sos. Panduri, Bucharest 5, 050663, Romania.
2. Aspirin. Retrieved May 11, 2014 from
http://en.wikipedia.org/wiki/Junior_aspirin.
3. Fourier transform infrared spectroscopy. Retrieved May 11, 2014 from
http://en.wikipedia.org/wiki/Fourier_transform_infrared_spectroscop
y.
4. Holler, Skoog& Crouch (2007). Principles of Instrumental Analysis
(6
th
ed.). Thomson Brooks/Cole.