Pharmaceuticals and Related Drugs D. W. Cornish, D. M. Grossman, A. L. Jacobs, A. F. Michaelis,’ and B. Salsitz Pharmacy and Analytical Research Department, Sandoz- Wander, Inc., East Hanover, N.J.
The review covers the period between June 1970 and June 1972. It encompasses the literature pertaining to t h e analytical chemistry of pharmaceuticals and related substances. The information has been arranged in the usual tabular format. The bibliography includes a cross-reference to Chemical Abstracts (C.A.) or Analytical Abstracts (A.A.) in order to facilitate the gleaning of information from the less widely circulated journals. The survey reflects a n increased number of publications in this scientific area. Chromatographic procedures continue to become more popular as methods were devised for assaying specific molecules. The numerous gas and thin layer chromatographic methods have been joined by 1 To whom reprint
requests should be directed.
the relatively new high pressure liquid chromatographic procedures for separating mixtures of compounds. Automation is another area of increased growth, spurred by content uniformity testing requirements for dosage forms. Interest in polarography has been revitalized as a result of improved instrumentation for this technique. More references have been made to nuclear magnetic resonance as a tool for qualitative and quantitative determinations. The use of the sensitive fluorimetric methods has been reported in increased number. The legal and social problems of drug abuse have stimulated activity in the field of identification of drugs. Chromatographic and spectrophotometric techniques have been extensively applied to narcotics, sedatives, and stimulant drugs.
-Table I. Alkaloids Compound or class
Alkaloidal amines Ephedra alkaloids Ephedrine
Methylephedrine
Method or subject
Reference
Ultrasonic extraction Automatic analysis Chromatographic,gas Chromatographic,ion exchange Chromatographic, thin layer Colorimetric Identification Review Spectrophotometric, ultraviolet Volumetric, iodometric Volumetric, nonaqueous Colorimetric Spectrophotometric, ultraviolet
(7986) (437) (2560) (2737) (7 738) (594, 7304) (910) (735) (357) (7459) (7 749) (7007) (7068)
Chromatographic, column Chromatographic,gas Chromatographic,miscellaneous Chromatographic, thin layer
Colorimetric Complexometric Electrophoresis Identification Microcrystallographic Polarimetric Polarographic Review Spectrophotometric, ultraviolet Volumetric, acid-base, nonaqueous Volumetric, potentiometric
(240, 702, 803) (337, 7040, 7606, 2344) (377, 733, 705Ei) (677, 792, 864, 937, 7029, 7049, 7057, 7897, ;?009,2729, 2752, 2759, 2760, ;?327, 2322, 2389, 2390, 2484) (7902) (979, 1785, 7747, 2798) (2723, 2527) (909, 7358) (77oj (7972) (7030, 7268) (373, 375, 204.[, 2479) (7078) (335, 7247, 7530, 7937, 2639) (7075)
Chromatographic, gas Fluorescence Colorimetric Chromatographic,thin layer Chromatographic,paper Microcrystallographic Automatic analysis
(726) (2320) (7 756) (323) (7380, 2346) (768) (414)
Alkaloids,general methods
AI kaloids, miscellaneous
Acronine Brevicoline Cytisine Fagara alkaloids ’ Glauclne Lupine alkaloids Nicotine alkaloids
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Table I. (Continued) Compound or class Pachycarpine Pilocarpine
Radix valerianae Securinine Zingi b e r a c e a e Indole alkaloids Ajmaiine
Arichine Brucine Bufotenine Ergot alkaloids
lndanol derivatives Lysergic acid diethylamide
Physostigmine
Psilocybin Rauwolfia alkaloids
Reserpine
Strychnine
Vinca minor alkaloids Yohimbine lsoquinoline alkaloids Apomorphine Benzomorphan derivatives Berberine
Boldine Codeine
D i a m o r p h i n e (heroin)
Diethylmorphine Dihydrocodeinone
222 R
Method or subject
Reference
Photomet 'ic Chromatographic, thin layer Colorimet 'ic Kinetic Review Coloriniet ,ic Polarimet 'ic Spectropt citometric, ultraviolet Chromatographic, thin layer
(2278) (607, 7436) (785, 876, 7085) (7908) (301 (2508) (7254) (2097) (7986)
Colorimet 'ic Identificalion Volumetri :, nonaqueous SpectropFotometric, ultraviolet Colorimet 'ic Fluorimeti ic Colorimet 'ic Chromato araphic, paper Chromato araphic, thin layer
(2052, 2749) (2605) (2749)
Chromatoaraphic, gas Identificaiion Microcrys taliographic Spectropl-citometric, ultraviolet Chromato araphic, gas Chromato j r a p h i c , thin layer Colorimet .ic Colorimet 'ic Chromatoaraphic, paper , Chromato graphic, thin layer Fluorimetric Volumetri 2 , acid-base, nonaqueous Automatic analysis Chromatoaraphic, thin layer Colorimet .ic Fluorimet 'ic ldentificai ion Spectropt otometric, ultraviolet Chromatographic, thin layer Co1orimet:ic Coulomet 'ic ldentifical ion Spectropt otometric, ultraviolet Fluorimet 'ic
Colorimet ,ic Volumetri 2 , acid-base, nonaqueous Chromatographic, thin layer Volumetri 2 , acid-base, nonaqueous Bioassay Colorimetric Fluorimet 'ic Spectroptiotometric, ultraviolet chromatographic, gas Colorimetric Automatic: analysis Chromatcgraphic, c o l u m n Chromatcgraphic, thin layer Colorimel tic Complexc,inetric Radioactivge Spectropliotometric, ultraviolet Chromatc graphic, column Chromatc graphic, gas C h r ~ m a t c ~ g r a p h i cthin , layer ldentifica tion Chromatcqraphic, thin layer C o l o r i m e ric
ANALYTICAL CHEMISTRY, VOL. 45, NO. 5, P I W I L
1973
(75) (584, 2575-2577)
(7587 ) ( 7 75 7, 2438) (7200) (252, 775, 786, 7758, 7989, 7990, 2487, 2555) (200) (7473, 7489, 7627, 7622) (76Q) (7589) (2374) (2747) ( 7 722) (687) (236 7 1 (426, 7752) (7059) (780) (7684) (7495, 2050) (787, 2788, 2789, 2422) (739, 714, 2423) ( 798 7) (572, 7208) ( 7 768) (584, 7093, 2575-2577) (7074) (7894) (403, 545) (773)
(7893) (2628) (995, 7080) (7408) (7994, 7995)
(445) (378, 2542) (2364) (7843) (2040) (390) (2702) (258, 259, 637) . (7302, 7739, 2027)
(465) (2678) (7036) (7574) (457,470)
(457) (1878)
(7765) (236, 2095)
Table 1. (Continued) Compound or class Dihydromorphine Hydrastine
Lemoran Lycorenine Morphine
Morphine derivatives
Nalorphine N a r c o t i n e (noscapine)
Opium Opium derivatives
Papaverine
Salsoline
Method or subject
Refetence
Identification Identification Chromatographic, thin layer Fluorimetric Gravimetric Spectrophotometric, ultraviolet Colorimetric Chromatographic, gas Chromatographic, column Chromatographic, gas Chromatographic, thin layer Colorimetric Extraction Fluorimetric Gravimetric Identification Polarographic Spectrophotometric, ultraviolet Volumetric, acid-base, nonaqueous Chromatographic, thin layer Colorimetric Fluorimetric Colorimetric Chromatographic, column Chromatographic, ion exchange Volumetric, acid-base, nonaqueous Chromatographic, column Chroma!ographic, thin layer Chromatographic, gas Chromatographic, gel Chromatographic, thin layer Fluorimetric Spectrophotometric Volumetric, acid-base, nonaqueous Colorimetric Complexometric Spectrophotometric, ultraviolet Volumetric, iodometric Colorimetric
(2635) (2635) (468) (2580) (2568) (2797, 2668) (7347) (2275) (2073, 2738) (678. 996) (380, 477, 600. 7807) (7672, 2039, 2150) (906) (7559) (7055, 2074) (7667, 2634) (7627, 7876) (7064, 7303, 7305, 251 1 , 2579) (7668) (930, 937, 79281) (7274, 7962, 2 i 4 8 ) (2547) (7257) (624) (7202) (7087) (2740) (257) (7608, 7693) (793) (277, 378, 7042, 7437, 1932, 2270, 2275) (360) (778, 7065, 2249) (7669-7677) (2072, 2279) (7658) (79, 7098, 2250) (7579) (2757)
Polarographic Volumetric, acid-base, nonaqueous Chromatographic, paper Chromatographic, thin layer FI uorimetric Spectrophotometric, ultraviolet
(500) (7) (7825) (907) (900, 7438) (837, 2062, 2739)
Colorimetric Volumetric, acid-base Chromatographic, gas Chromatographic, gas
(7088) (374) (326, 7306) (2546)
Isoquinoline, bis-benzyl alkaloids Emetine Ipecacuanha alkaloids
Pyridine alkaloids Lobelia alkaloids Nicotine Tobacco alkaloids Pyrrolizidine alkaloids General Platyphylline Quinoline alkaloids Cinchona alkaloids
Echinopsine Quinidine Quinine
Electrophoresis Colorimetric Chromatographic, paper Chromatographic, thin layer Review Volumetric, acid-base, nonaqueous Fluorimetric Spectrophotometric, visible Chromatographic, thin layer Colorimetric Dielectric constant Fluorimetric Spectrophotometric, ultraviolet Volumetric, ox.-red.
(2499) (62, 2235) (24 78) (7359) (508) (2369) (232) (7777) (7612) (7928) (907, 963, 237 2) (7656)
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Table I . (Continued) Compound or class Steroidal alkaloids Jervine derivatives
Solanidine Solasodine
Tropane alkaloids Atropine
Belladonna alkaloids
Cocaine
Homatropine Hyoscyamine Methylatropine Methyl homatropine Scopolamine Solanaceous alkaloids Tropane alkaloids Tropinone Xanthine alkaloids Caffeine
Theobromine Theophylline
Xanthines, general
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Melhod or subject Chromatclgraphic, paper Chromatcqraphic, thin layer Complexoinetric Colorime ric Complexoinetric Volumetr c , acid-base, nonaqueous
Reference
(24 7) (247) (2362) (67,7699) (238 7 ) (273)
Automatic: analysis Chromatcgraphic, gas Chromatcgraphic, paper Chrornatcgraphic, thin layer Color imei ric Complexc rnetric Electrophgresis Fluorimetric S p e c t r o s w p i c , reflectance Spectroptii)tometric, visible Spectroptiiitometric, ultraviolet Volumetric, acid-base, nonaqueous C h ro m a to graphic , t h i n I ayer Colorimetric Complexc rnetric Spectrophotometric Volumetric, acid-base Chromatographic, column Colorimetric Spectrophotometric, infrared Colorimetric Chromatographic, gas Chromatoeraphic, thin layer Chromatographic, paper Complexc rnetric Volumetric, potentiometric Chromatopraphic, gas Spectropliotometric, infrared Chromatographic, thin layer I d e n t i f i c a ion Chromatographic, gas Colorimetric Chromatographic, thin layer
(47, 48, 2352) (835. 7607, 7609, 2763) (7833, 7834) (534, 667, 1779) (7830, 2368, 2569, 2570) (466, 7720, 7721) ( 7 746) ( 7 922) (7837) (657) (7063, 7376) (2778, 2572-2574) (945, 7571, 7824) (203, 7326, 7367, 7832) ( 7 755) (2444) (7333) (7575) (7659) (764 7 ) (668) (393, 7497. 2653) ( 7 729, 2593) ( 7.860) (26, 2267) (834) (393, 7497, 2653) (1492) (36, 2783) (64 7 , 2606) (8, 7794) (206, 2371) ( 7 795)
Chromatocraphic, gas Chromatographic, thin layer Colorimetric G rav i m e t I i c Volumetri s, ox.-red. Complexc metric Extractior Chromatographic, thin layer Extractior, ldentificai il3n Spectropkotometric, ultraviolet Volumetris, a m p e r o m e t r i c Chromatographic, thin layer Colorimetric Identificai iim Spectropt otometric, ultraviolet Volumetri z , acid-base, nonaqueous Volumetri 3 , argentimetric Volumetri:. ox.-red.
(256, 2055) ( 7 168) (7233) (7000) (2676) (7463) (2089) (2027) (2088) (2607) (1677) (2532) (588, 7237, 7439, 2274) (237, 7728) (653, 7983) (955) (2577) (7737) (1845-7847, 2248)
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Table I I . Antibiotics Compound or class Antibiotics, general methods
Aureofungin Bacitracin
Capreomycin Carbomycin Cephalosporin
Chloramphenicol
Chlorotetracycline
Cycloserine Doxycycline Erythromycin
Furacilin Gentamycin Griseofulvin
H yg r o m yc in Kanamycin Lincomycin
Neomycin
Oleandomycin Olivomycin Oxytetracycline
Paramomycin Penicillin
Method or subject
Automatic analysis Chromatographic, gas Chromatographic, ion exchange Chromatographic, paper Chromatographic, thin layer Electrophoresis General method Identification Polarographic Spectrophotometric, ultraviolet Chromatographic, thin layer Chromatographic, miscellaneous Chromatographic, paper Colorimetric Electrophoresis General methods Colorimetric General method Colorimetric Chromatographic, thin layer Colorimetric Vo Iu met ri c, acid- base Volumetric, ox.-red. Biological Chromatographic, gas Chromatographic, thin layer Colorimetric Polarographic Volumetric. acid-base Chromatographic, thin layer Identification Fluorimetric Volumetric, amperometric Colorimetric Chromatographic, thin layer Biological Chromatographic, gas Chromatographic, thin layer Identification Spectrophotometric, infrared Colorimetric General method Colorimetric Polarographic Volumetric, iodometric Chromatographic, ion exchange Biological General method Biological Chromatographic, gas Chromatographic, thin layer Spectrophotometric, infrared Thermal Biological Chromatographic, gas Chromatographic, ion exchange Chromatographic, liquid Chromatographic, gas Spectrophotometric, ultraviolet Chromatographic, column Chromatographic, paper Chromatographic, thin layer Fluorimetric Spectrophotometric, ultraviolet Biological Automatic analysis Biological Chromatographic, gas Chromatographic, thin-layer
Reference
(777,942, 7384) (299) (587) (227,592, 2772) (250.7792,7642, 7643,20;'7, 2507, 2667) (7386) (2072) (98,578, 7968,2049, 2375,2578,2522) (556) (7867) (297) (334) (2239) (2239) (2239) (7338) (2486) (82) (7272) ( 7 78,204, 205) ( 7 782) (395) (7848) (7667,2477) (7475) (896,7027) (7092,7 789,2074,2762) (423,699) (7533) (536) (2636,2642) (536) (57) ( 7 783) (2756) (70, 7206) (2376) (7398-7400,7957) (85) (85,7782) (68) (83) (2477) (2478) (2475,2476) (7879) (74,2376) (2375) (87) (2724) (2724) (7600) (7600) ( 2469) (2374,2440) (2469) (570,7392) (1975) (7927) (727) (2722) (2755) (2722) (727) (75) (642,856, 7050, 7490,7646,2279,2547) (856,7050) (729,960) (770,210,695,893, 7793-7,'96,7482, 7577,2125)
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Table 11. (Continued) Compound or class
Polymixins
Rifamycin Streptomycin Syn thomycin Tetracycline
Thiamphenicol Trichomycin Tyrothricin Viomycin Antibiotics, general
Metliod or subject Colorimetric Identification Polarimetric Spectrophoto metric, infrared Spectrophoto rietric, ultraviolet Spectroscopic:. nuclear magnetic resonance Volumetric, a :id-base, nonaqueous Volumetric, c i m p l e x o m e t r i c Volumetric, c i u l o m e t r i c Volumetric, o
