Lal, B B

Verma, S P

English

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Indian J .  Fhya. 51 A, 324-328 (1077)Infrared studies of some analgesic group commercialtablet samplesB, B. L a l  a n i> S. P. V a b m aInfrared Section, National Physical Laboratory,Hillside Road, New Delhi 110012{Received II March 1976, revised 9 September 1976)Tli(i infriiicxl absorption spectra of some analgesic group commercial tablet samplas Kavc Ixum reccyrdc^ d in t,ho spcjctral region 650-6000 cm'^A ccimparatiFe study of tlu^  iulVarod spoctrti of these tablet samples has been carried out. A collection of these S]*ectra is given and manj'^  of the o])Hcrvod bands whicjh may Ijo useful in understajiding the structural behaviour have been assigned to specific functional group.I . Tn t r o d u o t io hA survey (d’ the earlier literat.ure on the structural studies of analgesic group tH)inmer(Mal tablet reveals tluit v(’*ry little effort, has been made in this direction. Prom t,ho quality cont rol point ol‘ view, a inedhod of analysis of pharmaceutical products (containing caffi(uie. accdylsalicylic acid and phcnacetin compounds has been des(*rihed by Parke ef aZ (1951). They have recorded five infrared spoclrn of those mixtures only in Mie legion 1430-2000 cm“  ^ in CHOl^  solution and by applying B(Kn -Bouguort's law, conceiit vation of each coustiiuenti was pn^dicted. The presoirt paper deals with t.he uKcasuremoiit of infrared spectra of five ana- lg(\sie commercial iabket samples, the comparison of their spectra, and t he assign­ment of some common functional groups.2. ExPliRlMENTALIn the present i!)V(cst-igation, five tablets of commercial trade name ; aspro, aiiacin, avedan, saridon, and analgin which show, especially, analgesic behaviour wore taken These tablets of standard make wore obtained from the general pharmacisi.s. Par their infrared studies, KBr pellet technique was employed, fn making tlu' tablet., fixed ratio of the tablet and anhydrous KBr was used for all the saui]>les. All tlie spectra were recorded cm a Hilger infrared spectre l>hotoinotor (model H-800) in f he region 650-5000 cm' .^ A number of spectra Avere taken for each tabket sample.3 R e s u l t s  a n d  D is c u s s io nTabic 1 lists the repoi’led constituents of these analgesic tablets, whereas figure 1 shows the chemical structure of these constituent compounds. From those structures, it may b(>> realised that due to heavy substitution of methyl,324acetyl, ethoxy, hydroxyl and oa-rbonyl groups, the spectral behaviour of the luixture compounds fresent in (‘ach tablel will be very complex. H()\vc»vei', there are some oorninon functional grou})s iu each ta])lot sainples, which may provide some definite clues regarding the nature ol the molecular vibrations. In the present case, the magnitudes ol Ireqmmcy and its iuteiisity r(>latod to a. specific functional grou]) in a compound may be a-lieet-cd eitlu'r bv its own inter-Infrared studies of some analgesic group samples 325a0 “ C -  CM, II0(ii) AccTyi' fiollcyiic acidoc0 -jj-C H ,-0(III) A ce ty l-p  - ominophenol (iv) Phcnocfttin(v ) Diethyl -  dIoRO-letrohydropyridlne (vl) Quinine sulphateH,C-Cr « 5  H CM,HgC----- C ---------M O O S O --C -« -C1 ” Ic — c ^ oIC»MjC -C M ,1N -C M -(vii) Phenyl-dimelhyl-leoprapyt-pyrazolone.Ivin) N -  m ethyl- melubrin Fi,. IFig. 1. Tho chomical stnicturo of (lonHtiOimit compouiuiK ui analgoHic 1 able'I nampInHand/or intra molecular interaction or by interactions of the molecule of other compounds present in tho tablet. Also, the presences of twn or more iluin two types of molecules in one tablet causes superposition of sev(ual types of vibration in the overlapping region. Due to this kind of superposition, the assignment of the observed frequencies becomes some what more difficult.326 B. B. Lai and S. P. VarmaTablo 2 littts the stroteliing frequencies alongwith t-elativo intensities corres­ponding to the (common furietionpl groups observed in figure 2. The spectral rang(i of thes(3 stretching frequencies arc very well laiown and can 1)0 identified easily (Bcillanij^  1954, Lai 1971, Lai el id 1972). Here only stretching mode have b(3on considiirod bf‘eaus(3 these modes are (expected to have greater transition prohabilitv tban their defonnation modes. It is evident from Table 2 that most of these frecpioiicies a])p(?ar with apj»reciable iiittmsity. Howevei*, the stretching fr(?qnencies bf^ Iongiug to 0-H and C-H (iu plu^njd ring) are not well defiiied. Due to inter moleeiilar hydrogen bonding (8)ioppard 1959), tlie 0-H stretching frequeiicy lias b(Hm identitied as indicated in Table 2. We also infer from the spectra the absenc(3 of hydroxyl gjoup in both saridon uiid analgin. .Fig. 2 shows that the stretehijig frequencies listc^ d in Table 2 I'xe^ p^t O-Il and C-11 bonds ar<3 not much aflocted eilLcu* by th(3 molecular inteiactions oi’ by the superposition.I , ) ! ? '  I■■ ;r, ; ij,ji '\',j /.I 1"- WAVt NUMBEFl (Cm )Fig. 2. Infrari'd sportrn of analgesic tablol/ samploR.The C—O stretching freqiumcy is no/mally observed in the region 1630- 1850 cin-^ In tlu‘ prevsent study, the C = O groups involved in the constituent compounds of the tablet samples ar(^  Jiiainl^ - attached to the acetyl and amide groups. In case of acetyl group, the C ^  O stretching frequency is observed near 1740 cm'  ^ (ovorond and Scherer I960) and in amides it appears in the I'egion1680-1680 cra~^  (Richards and Thompsoji 1047). As mddoni iVoni Tahiti I and Fig. 1, in analgin C ^ 0 grovip is atiaelual with tlui sii’ondary ainidr AvluTcas in aspro, aiiacin and aA^ edan it is associated with amides and acetyl gjoujis bolln AV'liilo aeetyl groups are domimait. As in llies(^  acetyl gruiqvs, an el(‘etroi ANilh- drawing j)ltonyl group is placed on the single famdod oxygon, the eaibonyl i'vr ({uency will be raised. Tluis the strojig bands at 1640 em^  ^ iii analgin and around 1740 eni"^  in aspro, anacin and aA culan lias been attributed to 0 0 stretchingmode. Tn case of saridon, in addition t o amid(\s and aeidyl grou]>s of (^ arliej' thnu^  tablets, a secondary ajuide group is also attached Avith th(^  caibojiyl. In aiuid(\s th('. dominent olfectp is tlu' inesomej ic (dTect nhicli residts a AA caher (/ = 0 btmd ajullowering of its stretching frecpieney. Consequently, witli combined effect of acetyl amides groups, tlu^  C ~ 0 stretching frecpieney in saridon has been ident.i- fled at 1680 cm~^ .Table 1 . Commer(‘ial tabletri and tlioir j cportod constituentsInfrared studies of some analgesic group samples 327TablotsAsijroAnaomAvo6ii.iiSiiridonAnalginGonstitutmi curnpauiicJH (Koportod)(Jaffoiiii', and ao(vfcylHalicyli<5 acid*.(latroiiio. acotyItalicylic* acad*, and qiiiiiiiuj suliiliatt'Caflbino, ai't tylHaLic*Adio acid*, and ac(dyl-p nnnnojdicintlOaffcvinc, Phcnacotiii, Pluuiyl-dimcthyl-is^qnnjivl pyrazcloiir., and Dio thy 1-til ox o - toira'hydropyi id in r * *.Novalgin (N-mothyl-moluT>rin***).*Ac( tylHalicylic a(‘id is also known as Aspirin.**Diotliyl-dioxo-totrahydropyridiuo may also lx callod as DinHioxydnhahvdropyiidinf ***M oliihriji is Sodium-imtipyrino-aiuino*moihanosulfona1 c.From theoretical calculathm (Hojzborg 1945), strotehiiig mode is pre­dicted at around 900 eiu“ .^ Wheji tlm e^ iiydj ogeji atoms are assoeiabul Avith one of the two carbon atoms i.e., due to inei i^ ase in mass, the C-CTJ;, strotehiiigmode is expected to bo lower than C-0 stret ching frequmiey. Bastnl on this prin­ciple, O-OH3 stretching fj oquoncy has been assigned at 7H5 em“  ^in ease of toluene (Pitzer Scott 1048) and at 758 cm “^ in ease of 0-lluorotolnene (Joslii tS: Singh 1967). Thus, our assignment of 0  stnd.ehiiig mode aiound 800 enr  ^as shown in table 2 seems reasonable.The different kinds of base matrices, if any, from one typo to other type of tablet can be deduced by comparing those spectra. Further work towards evolv­ing a jww method for quality control of such type of analgesic tablets and d(3ter- miuing the adulterant, if any, is in progress and will be presented elsciwhere.Table 2 . Stretching moden of (sommon functional groups in the tablet328 B. B. Lai and S. P. VarmaAwjiro:>290 m:U()8 ni :i040 vs284 :i s 2725 Hh 2075 K1740 vvH1007 vs1500 vs1500 s1204 vsU75 vs705 VH747 vs737 lUHFi'oquonfiioB (ern"^ ) &, thoir rolativo intensities Aiiaoin Avodan Saridon3224 m(br) 3252 w 3024 inw2798 2047 sh 2590 ms1743 vs1044 vs1580 sI5K) insJ2 0 J s1176 VH795 H747 H3100 vs 2972 Hh2787 inw  2039 rriw1738 h 1072 vs 1044 VK 1595 K 1204 Hh(bi) 1186 vs 825 in 788 iiivbr) 741 mw3112 Hh3024 K2890 s 2771 sh 20751080 vvsJ038 vvs1590 vvs1541 vvsnoo VH775 s 741 s 737 H-Analgin Assignment0-H stretching3050 m 't 2990 Hh J ^C-H stretching in phonnlgioup2847 ms  ^2766 Bh 2090 sh J1 C-H stretching in i^n CHg group1640 vvs C — O sti"otching1612 vvs C C stretching1570 s 0  ”  C stretching0  = C stretching1178 vvs C-N stretching- - C-OH stretching769 ms C - CH 3 Htret ching752 s N-CHs stretching745 s N-CH3 stretchingrn, inodium : very ;U1S, modiuui sl.roap ; mw, medium w^ak ; s, Htioiip ; vs, very strong : veryw, Weak intousitios : hIi, sht>uldn‘ ; hi', broad. 'A cknowledgmentsThe authors wish to thank Piof. A. R. Verma  ^ Director, and Dr. V. G. Ghide for thoic keen interest in the work. Thanks are also due to Mr. N. K. SnVastava IVir ln‘s hol|) din ing the operation of infrared spectrophotomete]*.R eferencesHollainy L. 3. 1954 Jnfram l Spectra of Complex Molecules, Methuon and Co. Ltd., London Hi^ 'zbt'rg (4. 1915 Infrared and Ttaman Spectra, of Polyatomh' MolecalcB, D. Van NostrandOomp. Inc., 195..loalii Ck Sl 8High N L. 1967 Spcctrochini Avia 23A, 1341.Lai Ik n. 1971 Spectral Studies tn Organic Molecules^ Ph.D. TT:iesiSj Banara.s HinduXTnivereity, India.Lai Ik Ik, Srivastava M. P. & Singh I. S. 1972 Ind. J .  Pure and A^yplied Phys. 10, 400. Ovorond 3. h  Schoror 3. K. 1900 Spectrochi Acta 16, 7V3.Parko r .  V., Kibloy M., JConnody E. F. *  Hilty W. W. 1951 Anal Cliemiatry 23, 953. Pitzt>r K. S. & Scott D. W. 1943 J ,  Am. Chem. Soc. 65. 803.Richards R. E. &; Thompson H. W. 1947 J .  Chem, Soc. 1248.Sheppard N. IW} Hydrogen Bonding, ocl. by D. Haddzi & H. W. Thompson, PergamonPress, $6.

Infrared Studies of some Analgesic Group Commercial Tablet Samples

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Infrared Studies of some Analgesic Group Commercial Tablet Samples

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