The essential oil from the aerial parts ofA. millefoliumL. (yarrow) plants growing wild in Estonia was isolated by steam distillation extraction during 2 h of distilla- tion [38] and analyzed by GC–FID and GC–MS as described above. The results
Identification of Terpenes 491
Table 4 Identification Parameters (RI, m/z) and Relative Peak Areas (%) for Terpenoic Constituents of Essential Oil fromAchillea millefoliumL.
RI %
Major peaks of MS
No. Compound OV-101 PEG 20M OV-101 PEG 20M (m/z)
1 Tricyclene 917 1017 tr tr 93, 121, 41
2 α-Thyjene 921 1029 0.3
7.5 93, 77, 91
3 α-Pinene 930 1029 6.5 93, 92, 91, 77, 79, 121
4 Camphene 940 1074 0.8 0.7 93, 121, 79, 67, 107
5 Sabinene 965 1125
28.4 14.2 93, 77, 41, 79, 91
6 β-Pinene 967 1116 13.6 93, 41, 79, 69, 91
7 Myrcene 982 1161 0.2 0.2 93, 69, 41, 79, 53
8 α-Phellandrene 994 1167 tr 0.1 93, 77, 91, 136
9 α-Terpinene 1008 1180 0.7 0.7 121, 93, 136, 91, 77
10 p-Cumene 1011 1270 0.9 0.7 119, 134, 91
11 1,8-Cineole 1019 1211
12.3 10.6 43, 81, 71, 108, 84
12 Limonene 1022 1204 0.4 68, 93, 67, 79, 121
13 (Z)-β-Ocimene 1027 1232 0.1 0.1 93, 79, 91.77, 105, 121
14 (E)-β-Ocimene 1038 1250 0.2 0.2 93, 41, 79, 53
15 γ-Terpinene 1050 1246 1.6 1.5 93, 77, 121, 136, 91
16 Terpinolene 1077 1283 0.2 0.2 121, 93, 136, 39, 79, 91
17 (Z)-Sabinene hydrate 1084 1544 0.2 0.1 43, 93, 71, 41, 81
18 Linalol 1086 1547 0.1 0.2 71, 41, 43, 93, 56, 69
19 β-Terpineol 1110 1558 0.3 0.2 43, 71, 93, 136, 69, 58
20 Camphor 1121 1515 1.0 0.9 95, 81, 41, 55, 68, 108
21 (Z)-Sabinol 1124 1648 0.1 0.1 92, 91, 83, 109, 70
22 Myrtenal 1135 1623 0.2 0.4 79, 107, 39, 91, 41, 77
23 Borneol 1152 1693 1.4 1.9 95, 41, 110, 55
24 Terpinen-4-ol 1161 1593 1.3 1.2 71, 111, 93, 43
25 Myrtenol 1168 1783 0.1 0.1 79, 108, 93, 41
26 α-Terpineol 1175 1693 0.8 b 59, 93, 121, 136, 79
27 Piperitone 1225 1720 0.1 0.2 82, 110, 95, 137, 41
28 Bornyl acetate 1267 1574 0.5 0.4 95, 43, 136, 121, 93
29 Geranyl acetate 1365 1755
0.5 0.2 69, 43, 41, 93, 68, 121
30 α-Cubebene 1365 1477 0.2 161, 105, 119, 91, 41
31 α-Copaene 1369 1486 0.1 0.2 119, 105, 93, 41, 81
32 (E)-β-Caryophyllene 1412 1589 5.2 4.6 93, 69, 41, 133, 71, 91
33 Aromadendrene 1438 1631 0.1 0.1 41, 69, 91, 93, 55
34 Sesquiterpene 1440 1636 0.3 0.2 69, 41, 93, 55, 91
35 α-Humulene 1443 1660 0.7 0.7 93, 121, 80, 204, 41
36 (Z)-β-Caryophyllene 1449 1667 0.1 0.2 41, 93, 69, 133, 71 37 Allo-aromadendrene 1464 1685 0.5 0.6 93, 91, 41, 69, 105, 161
38 Germacrene D 1471 1700 1.9 161, 91, 105, 119, 133
39 γ-Muurolene 1471 1709 2.6 0.4 105, 91, 119, 41, 204
40 Sesquiterpene 1471 1712 0.5 93, 119, 69, 41, 91
41 α-Muurolene 1483 1722 0.1 105, 161, 81, 93, 119
492 Orav
Table 4 Continued
RI %
Major peaks of MS
No. Compound OV-101 PEG 20M OV-101 PEG 20M (m/z)
42 (Z,Z)-α-Farnesene 1483 1733 0.3 0.2 41, 63, 69
43 (Z,E)-α-Farnesene 1483 1740 0.1 41, 63, 69
44 (E,E)-α-Farnesene 1490 1742 0.3 0.3 41, 93, 69, 55, 107 45 β-Bisabolene 1494 1737
0.5 0.3 69, 41, 93, 161, 204
46 γ-Cadinene 1497 1747
0.8 161, 105, 91, 119
47 δ-Cadinene 1510 1749
0.8 161, 134, 204, 119
48 (R)-Cuparene 1512 1766 0.2 132, 145, 119, 105
49 α-Bisabolene 1533 1762
0.3 0.1 69, 41, 93
50 (Z)-Nerolidol 1533 2028 0.2 41, 69, 134, 91, 93,
79
51 (E)-Nerolidol 1549 2035 4.2 4.0 69, 41, 93, 43, 71, 55
52 Unknown 1562 2077 0.4 0.6 69, 41, 43, 81, 93,
55
53 Caryophyllene 1565 1968 2.3 2.4 41, 43, 79, 69, 93 oxide
54 Veridiflorol 1575 2069 0.4 0.6 43, 41, 69, 109, 161
55 Ledola 1588 2100 0.3 0.3 43, 69, 41, 122, 81
56 Unknown 2110 0.3 59, 143, 105, 41, 43
57 Guaiol 1608 2126 1.5 1.5 59, 161, 107, 41, 81
58 β-Bisabolol 1614 2142 0.3 0.3 81, 98, 41, 111, 119, 69
59 δ-Cadinol 1624 2156 0.7 0.5 161, 43, 119, 109, 204
60 T-Cadinol 1624 2161 0.5 161, 204, 105, 134
61 T-Muurolol 1630 2172 0.6 0.7 95, 43, 121, 161, 204
62 Unknown 1633 2192
0.1 0.5 119, 41, 69, 93, 43
63 α-Cadinol 1633 2218 0.4 95, 121, 204, 43, 164
64 Caryophyllenol II 1637 2237 2.2 1.7 43, 81, 189, 161, 55
65 Farnesola 1652 2255
0.5 0.3 69, 41, 93, 81
66 Farnesola 1652 2275 0.2 69, 43, 93, 81
67 Unknown 2293 0.9 136, 41, 69, 91
68 Unknown 1659 2360 1.2 1.2 41, 109, 91, 43, 55
70 (Z,E)-Farnesol 1665 2347
2.1 1.1 69, 41, 81, 93
71 α-Bisabolol 1665 2205 1.1 109, 119, 69, 204, 93
72 Chamazulene 1700 2373 2.3 2.0 184, 169, 183, 153
aCorrect isomer not identified.
bEluates with borneol.
tr⫽traces (⬍0.05%).
Identification of Terpenes 493
of the identification of terpenoic constituents of yarrow oil and percentage quanti- ties of peaks are presented in Table 4. The yarrow oil was a complex mixture of approximately 100 compounds, 65 of which were identified as representing up to 90% of the total oil. The main groups of components in this oil were monot- erpenes (55%), while oxygenated sesquiterpenes constituted 20%, sesquiterpenes 12%, and oxygenated monoterpenes 6% of the total. The peaks of the main com- ponents in oil, sabinene, andβ-pinene overlapped on OV-101 column, but were separated on PEG 20M. The peaks of limonene and 1,8-cineole also overlapped on OV-101, but from the PEG 20M data it can be concluded that 1,8-cineole constituted about 10% and limonene only 0.4% in this yarrow sample.
The main difficulties occurred in the identification of sesquiterpenes and oxygenated sesquiterpenes. There are many overlapping peaks (especially on OV-101 column) and insufficient literature on RI data in the polar phase for sesquiterpenes and oxygenated sesquiterpenes in these regions of the chromato- grams.
ACKNOWLEDGMENT
We thank Dr. M. Mu¨u¨risepp for performing GC–MS analyses.
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Appendix
AC acetylation
ACE angiotensin converting enzyme AED atomic emission detector AGC automatic gain control AMS accelerator mass spectrometry AP appearance potential
ASI associative surface ionization
ASTED automated sequential trace enrichment of dialysates AT-II angiotensin receptor II blocker
beta-BSCD tert-butyl dimethylsilylated-beta-cyclodextrin
beta-TBDM heptakis (6)-tert-butyl-dimethylsilyl-2,3-di-O-methyl)-beta-cyclodextrin BSA bis-trimethylsilylacetamide
BSTFA N,O,-bis-trimethylsilyl-trifluoroacetamide BTEX benzene, toluene, ethylbenzene and xylenes CAH congenital adrenal hyperplasia
CFS continuous-flow systems CI chemical ionization
CID collision-induced dissociation CSP chiral stationary phases DHS dynamic headspace
DMA dimethylamine
DPA diphenylamine
DSI dissociative surface ionization ECD electron-capture detector
ECNI electron-capture negative ionization EI electron ionization
ELCD electrolytic conductivity detector FI field ionization
FID flame-ionization detector FTIR Fourier-transform infrared FTR fractional turnover rate
GC gas chromatography
495
496 Appendix
GC-C-IRMS GC-combustion-IRMS GC-P-IRMS GC-pyrolysis-IRMS
HFB heptafluorobutyric ester, heptafluorobutyration HFBA heptaflurorbutyric anhydride
HFBI heptafluorobutyric imidazole HFIP hexafluoroisopropranol
HRGC high-resolution gas chromatography HRMS high-resolution mass spectrometry HSD hydroxysteroid dehydrogenase IASPE immunoaffinity SPE
IE ionization energy
IR infrared
IRMS isotope-ratio mass spectrometry IS internal standard
ITD ion-trap detector
IV intravenous
LAAM l-a-acetylmethadol LC liquid chromatography LLE liquid-liquid extraction LMCO low-mass cut-off LOD limit of detection
LRMS low-resolution mass spectrometry LVI large-volume injection
MBTFAN methyl-bis-(trifluoroacetamide) MFI multifrequency irradiation
MIDA mass isotopomer distribution analysis
MMA monomethylamine
MS mass spectrometry
MSD mass-selective detector MSI molecular surface ionization MS-MS tandem mass spectrometry
MSTFA N-methyl-N-trimethylsilyl-trifluoroacetamide MTBSTFA N-methyl-N-ter-butyl-dimethylsilyl-trifluoroacetamide NCI negative-ion chemical ionization
NMR nuclear magnetic resonance NPD nitrogen-phosphorous detector NSAID nonsteroidal anti-inflammatory drug PBM probability based matching PCB polychlorobiphenyl PCDD polychlorodibenzo-p-dioxin PCDF polychlorodibenzofuran PCI positive-ion cemical ionization PCSE partially concurrent solvent evaporation PCT polychlorinated terphenyls
PDB Pee Dee Belemnite PDMS polydimethylsiloxane
Appendix 497
PFB pentafluorobenzyl
PFB-Cl pentafluorobenzoyl-chloride PFP pentafluoro-1-propanol
PFPA pentafluoropropionic acid anhydride PLOT porous-layer open-tubular column
PT purge-and-trap
PTV programmed temperature vaporizer
RF radiofrequency
RI (Kovats) retention index RSI reaction surface ionization S/N signal-to-noise ratio
SCOT suface-coated open-tubular column SDE simultaneous steam distallation–extraction SFE supercritical fluid extraction
SFI single-frequency irradiation SFM secular frequency modulation SI surface ionization
SIM selection ion monitoring
SIOMS surface ionization organic mass spectrometry SPE solid-phase extraction
SPETD thermal-desorption SPE SPME solid-phase microextraction SRM selective reaction monitoring STA systematic toxicological analysis SVE solvent vapour exit
SVE solvent-vapour exit TBA tributylamine
TDM therapeutic drug monitoring TEA thermal-energy analyser TEF toxicity equivalent factor TFA trifluoroacetylation TFAA trifluoroacetic anhydride TIC total ion chromatogram TMCS trimethylchlorosilane
TMS trimethylsilyl, trimethylsilylation
TNA trimethylamine
TOF time-of-flight
TSQMS triple-stage quadrupole mass spectrometry WCOT wall-coated open tubular column
WSCOT wall-coated superior-capacity open-tubular column
499
Index
Acetic acid, 428 Acetone, 209, 424
Acetonitrile, N-morpholino-, 390 1α-Acetylmethadol, 378
Acridine, 44
Adenine, N-3-alkyl, 209 Aflatoxins, 219
Alachlor, 185
Aldehydes, 410–412, 427 Alfentanyl, 267, 273, 277 Alkaloids, 45
Alkylamines, 43–44
Alkylphenol ethoxylates, 473–474 Alphaprodine, 262
Ambient air analysis, 200–201, 202–207, 240–244
Amino acids, 45, 288, 291, 298–299 Aminoalcohols, 44
Ammonia, 209
Amphetamine, 252, 253, 358, 359, 364, 378–380
methylenedioxy, 364 Analgesics, 359
Androst-5-ene-3β,17β-16-keto, 314 Androst-5-ene-3β,17β-diol, 312,
314
5α-Androstane-3α,17α-diol, 315–
316
Androstanediol, 326, 329, 334, 464 4-Androstenedione, 326, 329, 333
Androstenedione, chloro, 461 Androstenetetrol, 314 Androstenetriol, 312 Androsterone, 312, 323–324
11-hydroxy, 312, 323, 325 11-oxo, 312
dehydro-epi- (DHEA), 312, 321, 325–326, 329, 334
15β,16α-dihydroxy, 314 16-α-hydroxy, 312, 314,
321
sulfate, 313, 329, 334–335 Anesthetics, 235–240, 267–281 Angiotensin converting enzyme in-
hibitors, 356
Angiotensin receptor II blockers, 356
Aniline, 35, 40, 163 dimethyl, 160, 171, 176 dinitro, 390–391 Anions
azide, 399–400 chlorate, 399–400 cyanide, 399–400 disulphide, 399–400 hydrosulphide, 399–400 nitrate, 399–400, 405 nitrite, 399–400 sulphide, 399–400 thiocyanate, 399–400
500 Index
Anisole
chloro, 412, 430 nitro, 391
trichloro, 412, 430 Antiarrhythmics, 360 Anticonvulsants, 359
Antidepressants, 359, 361–362 Antihistamines, 360
Anti-inflammatory drugs, 252 Antiparkinsonian drugs, 359 Arachidonic acid, 298
Aromatics, 69–71, 76, 79–80, 86–87 Articaine, 267, 269
Atomic emission detection, 27, 189–191, 279–280 Atrazine, 49–50, 158, 176, 179 Automated cleanup, 252–263 Barbiturates, 170, 257, 356, 358–
359, 362–363, 381–383 Benzaldehyde, 45, 181
2-hydroxy, 430 trinitro, 391
Benzene, 66, 74, 238, 240–244 alkyl, 70–71, 169
chloro, 169, 171, 174, 176, 178, 431
nitro, 391 dinitro, 390 ethyl, 240–244 hexachloro, 163 methoxy, 178
trinitro, 388–391, 394–395 vinyl, 430
Benzodiazepines, 170, 183, 257, 261, 359, 362, 381 Benzoic acid, trinitro, 391 Benzoylecgonine, 257, 261, 375–
377
Benzyl alcohol, 45, 430
Beta-agonists, 356, 362, 363, 469–
471
Beta-blockers, 359–360, 362 Betamethasone, 466, 469 Bile acid, 293, 296, 299–300 Biomarker analysis, 59–68 Biphenyl
4-amino, 201, 219
polychlorinated, 106–114, 129, 201, 473
Bisabolene, 487 Bisabolol, 445, 489 Boldenone, dehydro, 460
Bornadienes, polychlorinated (see Toxaphene)
Bornanes, polychlorinated (see Toxaphene)
Bornenes, polychlorinated (see Toxaphene)
Borneol, 438 Bromazepam, 381 Bromophos-ethyl, 171 BTEX Analysis, 240–245 Bupivacaine, 267, 274, 277 Butadiene, hexachloro, 163 Butanetriol trinitrate, 392 Butanoate, methyl, 429 Butanoic acid, 428
Butyric acid, 4-hydroxy, 343 Butyrolactone, 275
Butyrophenone, 360 Cadinene, 487 Cadinol, 489 Caffeine, 263 Camphene, 438
polychlorinated, 127, 136 Camphor, 438
Cannabidiol, 381 Cannabinoids, 380–381 Cannabinol, 380
delta-9-tetrahydro (THC), 380 Caproic acid, 2-oxo, 345 Carbamates, N-methyl, 163, 170
Index 501
Carbaryl, 185 Carbazole, 44 Carbofuran, 185 Carbohydrates, 297–298 Caryophyllene, 487
oxide, 489
Chenodeoxycholic acid, 299–
300 Chlordecone, 473 Chlorpyrifos, 158 Cholestane, 65–66
Cholesterol, 296, 299–300, 310–
311
Cholesteryl butyrate, 315 Cholic acid, 293, 299 Cimaterol, 470 1,8-Cineole, 489, 493
Clenbuterol, 455, 467, 470–471 Clinazolam, 275
Clostebol, 460 Cocaethylene, 376
Cocaine, 257, 261, 262, 359, 362, 375–377
Codeine, 259, 262 Copaene, 438
Corticosteroids, 311–325, 466–
469
Corticosterone, 311, 313, 322 11-deoxy, 322
hydroxy, 322 tetrahydro, 312
-11-dehydro-, 312
Cortisol, 311–313, 316–317, 322, 325, 466, 469
(20α-dihydro), 325 20α-hydroxy, 312 6β-hydroxy, 312, 325
6-hydroxy, tetrahydro-11-deoxy, 321
deoxy, 321
tetrahydro, 312, 317, 322–325 -11-deoxy-, 312, 316
Cortisone, 322
hydroxy-tetrahydro-, 314 tetrahydro, 312, 314, 322 α-Cortol, 6β-Hydroxycortisol, 312 β-Cortolone, 312, 314, 322 α-Cortolone, 312, 322
6a-hydroxy, 314
Coumarin anticoagulants, 356, 363 Coumestans, 475
Coumestrol, 475 Cyclohexene, 44 Cyclonite, 389 Daidzein, 475 DDT, 473 Decalactone, 428 Decene, 432
Derivatization, 22–23, 86–87, 210, 252, 271–273, 315, 328, 345–346, 358–359, 372–374, 459–461, 469, 471, 472, 474
Designer drugs, 253, 359, 364, 378–380
Dexamethasone, 466, 469 Diazepam, 381
Diazinon, 473
Dibenzofuran, polychlorinated, 97–106
Dibenzo-p-dioxin, polychlorinated, 97–106, 473
Dibenzothiophenes, 76, 84–85 Dibucaine, 277
Diesel fuel emission, 79, 202–205 Diethylglycol-dinitrate, 401 Diethylstilbestrol, 455
Difluoromethoxy-2,2-difluoroacetic acid, 270, 273
Dihydropyridine calcium channel blockers, 356, 363 Dimethamphetamine, 380 Dimethoate, 171
502 Index
Dimethyl disulphide, 428 Dimethylamine, 46–47
Dimethylenediphenyl diisocyanate, 201
Dioxins, 97–106, 143 Diphenol laxatives, 359 Diphenylamine, 36, 390 Dipicrylamine, 394 Diuretics, 356, 363
DNA adducts, 209, 215–222 Docosahexanoic acid, 298 Dodecalactone, 428 Dodecane, 43 Dodecene, 432
Drugs of abuse, 170, 247–263, 355–365, 369–384 Dynamic headspace, 411 Ecgonine, 261, 375–377 Edulans I and II, 417 Eltoprazine, 158
Enantiomeric analysis, 349–351, 416–417
Enflurane, 269, 273 EPA 8270 method, 75–76 Estradiol, 445–446, 456, 460, 472 Ethanol, 424
Ethion, 171
Ethyl acetate, 424, 428 Ethyl hexanoate, 429 Ethyl propionate, 424
Ethylene glycol dinitrate, 388, 392–396, 401
Ethylene oxide, 473 Etiocholanalone, 312
11-hydroxy, 312 Eucalyptol, 438 Explosives, zie
False negative results, 444–445, 447–448
False positive results, 445–446, 448–451
Farnesene, 487 Farnesol, 490
Fatty acids, 288, 298, 424, 428–
429, 432 3-hydroxy, 201 Fenchone, 432
Fenfluramine, 383–384
Fentanyl, 267, 270–272, 276–280 Flavones, 475
Flavours, 409–410, 421–438 Fourier-transform infrared spectros-
copy, 27, 280 Fragrances, 409–420 Fructose, 297
Furans, 97–106, 410–411, 428 Fusarium toxins, 201
GC, injection techniques, 3, 20–
22, 155–194 GC, on-line LLE, 162–163 GC, on-line SPE, 163–179 Genistein, 475
Geranyl acetate, 489 Germacrene D, 487 Glucose, 288, 297–298
Glutaric acid, L-2-hydroxy, 346, 349–351
Glycerol, 296–297 dinitrate, 392 trinitrate, 388 Glycine, 299, 302 Guaiacol, 430 Guanidine, nitro, 394 Guanine, N-7-alkyl, 209 Haemoglobin adducts, 215–222 Halothane, 235–240, 270 Heptan-2-one, 428 Heroin, 259, 377–378
Index 503
Hexamethylenetriperoxidediamine, 398–399
Hexane, 207, 427 Hexogen, 389
Human breath analysis, 200–201, 207–209
Humulene, 487 Hydrazines, 32, 44 Hydrocortisone, 466 γ-Hydroxybutyrate, 267
Hypoglycemic sulfonylureas, 356, 363
Imipramine, 49
Immunoaffinity chromatography, 457
Indolalkylamines, 460 Indole, 44
Internal standard, stable isotope, 276, 286, 327
Ionization
charge-exchange, 81–84 chemical, 11–13, 84
electron-capture NCI, 128–136, 142
field, 13, 84 surface, 31–54 Ion-trap
application of, 95–114, 148, 185–187, 199–224, 348 instruments, 16–17, 96, 289,
416
Isoborneol, 2-methyl, 430 Isobutanoic acid, 428 Isobutyl acetate, 429 Isocamphone, 432 Isoflavones, 475 Isoflurane, 235–240 Isoprene, 57, 209 Isoprenoids, 60–62 Isosorbide dinitrate, 392
Isotope-ratio MS, 67–68, 285–
302, 410, 417–420 Isovaleric acid, 428
3-hydroxy, 346
Ketamine, 267, 270, 273–274, 277–278
Lactate, 297 Lactones, 159, 428 Lactose, 288, 297, 301 Lactulose, 288 Lamotrigine, 364
Large volume injection, 20–22, 155–194
LC-GC
heart-cut, 158–162 techniques, 157–163 Leucine, 298–299
Lidocaine, 47–49, 262, 267, 270, 277
Limonene, 417, 420, 438, 493 -1,2-epoxide, 417
Linalol, 417, 489 Lindane, 176
Linoleic acid, 288–298, 412 Linolenic acids, 298, 412
Liquid–liquid extraction, 251, 343, 357, 372, 411
Lorazepam, 381 Lysergide, 381–383 Mabuterol, 470 Malathion, 473 Malonic acid, 345–346 Maltose, 288
Mebeverine, 159 Medazepam, 275 Mepivacaine, 277 Mercapturic acids, 209 Metallocenes, 45
504 Index
Metalochlor, 185 Methadone, 262, 378
Methamphetamine, 252, 261, 262, 378–380
methylenedioxy, 364 Methanol, 209
Methaqualone, 364 Methoxychlor, 473 Methylamine, 44, 46–47 Methylene dianiline, 201
Methyl-N-methylanthranilate, 428 Methylpyrrole, 412
Methyl-t-butyl ether, 71 4-Methyltetrahydropyran, 2-(2-
methyl-1-propenyl), 417 Methylthiouracil, 471
Metriol trinitrate, 392, 401 Mevinphos, 170
Midazolam, 267, 272, 275 Mirtazapine, 361
Monoterpenes, 411, 416, 432, 438, 486–487
oxygenated, 489
Morphine, 259–260, 359, 362 MS
analyte ionization, 10–13, 34–
37, 80–84
high-resolution, 15, 26–27, 84–
85, 136–142, 273–274 instrumentation, 10–18, 39–40,
289, 442–443
MS–MS, application of, 63–66, 97–104, 143–148, 374, 461
Multidimensional detection, 27–
28, 268–269 Muramic acid, 201 Muurolene, 487 Naphthalene, 66
1-nitro, 180 alkyl, 71
[Naphthalene]
methyl, 427 nitro, 390
polychlorinated, 119 Narcotics, 247–263, 355–366,
369–384 Nerolidol, 489–490 Neuroleptics, 360
Nitramines, 388–389, 392–394, 396–398
Nitrate esters, 387–388, 392–398, 401
Nitro musks, 392 Nitrobenzonitril, 390 Nitrocellulose, 387–388 Nitrocresol, 390 Nitrofluoranthenes, 207
Nitroglycerin, 388, 392–398, 401 Nitroglycol, 388
N-Nitrosamines, 219 N-Nitrosomorpholine, 390 Nitrous oxide, 235 Nonane, 432
Non-steroidal anti-inflammatory drugs, 252, 259, 356–357, 363
Nonylphenol ethoxylates, 473–474 Noralfentanil, 277
Nordiazepam, 381 Norisoprenoids, 411
Norketamine, 270–271, 277–278 5,6-dehydro, 270–271, 277–278 Nortestosterone, 168, 445, 464 Oct-1-en-3-ol, 430–431 Oct-1-en-3-one, 430 Octanoic acid, 298 Octene, 432 Octogen, 389
Olefins, 57, 68–69, 87–91 Oleic acids, 412
Opiates, 256, 257, 359, 377–378
Index 505
Opioids, 359
Organic acids, 160, 163, 171, 342–352
Organometallic compounds, 44–45 Oxazepam, 381
Oxoacids, 342, 345, 347 PAH, nitro, 201–202 Palmitic acid, 288, 293, 298 Paraffins, 69–71, 80, 88 Parathion, 473
Pentacaine, 274
Pentaerythritol, tetranitrate, 388, 392, 394–395, 398, 401 Pentan-2-one, 428
Pentane, 209
Perchloroethylene, 473
Pesticides, 49–50, 159, 163, 171, 179, 185–187, 191, 473 organochlorine, 119, 473 organophosphorous, 28, 163,
187, 191, 473 Phallandrene, 432, 486, 489 Phenanthrene, 76–78 Phencyclidine, 381–383 Phendimetrazine, 383–384 Phenol, 3-chloro-4-nitro, 180
chloro, 169, 430 dimethyl, 176 trinitro, 388
Phenols, 163, 170, 178, 183 Phenothiazine, 359
Phenylalanine, 299 Phospholipids, 299 Phthalate, 159, 171, 473
di(2-ethylhexyl), 201 Phytane, 62
Phytanic acid, 346 Phytoestrogens, 473–475 Picramide, N-methyl, 393–395,
398
Picric acid, 388, 394–395
Pinene, 417, 432, 438, 486, 493 PIONA, 69
Pipecolic acid, 287 Piperidine, 43
Polycyclic aromatic hydrocarbons, 44, 76–79, 201, 219 Porphyrins, 60–61
Pregn-5-ene,3β,17α,20α-triol, 312
Pregn-5-ene-3β,15β,17α-triol-20- one, 314
Pregn-5-ene-3β,16α,diol-20-one, 314
Pregn-5-ene-3β,20α,21-triol, 314 Pregn-5-ene-3β,21-diol-20-one,
314
Pregnanediol, 312, 316
Pregnanetriol, 312, 316–317, 321 11-oxo, 312, 321
Pregnanolone, 17-hydroxy or 15- hydroxy, 311–312, 321, 326
Pregnenediol, 312 Pregnenetetrol, 314
Pregnenetriol, 17-hydroxy, 321 Pregnenolone, 311
17α-hydroxy, 327, 329, 334 Prilocaine, 277
Pristane, 62
Process GC-MS, 72–74 Profiling
plasma steroid, 326–332 urinary steroid, 313–326 Progesterone, 311, 313, 456, 473
17-hydroxy, 321, 326, 329, 332–333
Propanal, 3-methylthio, 428 Propionic acid, 428
Propofol, 267, 270, 273–275, 279 Propylene glycol dinitrate, 392 Purge-and-trap, 411
Purine bases, 45
506 Index
Pyrazines, 411–415, 428 methoxy, 411
Pyrene
amino, 206, 213–215 hydroxy-amino, 209–215 hydroxy-N-acetylamino, 209–
215
N-acetyl-1-amino, 214 nitro, 79, 202–209 nitro-4,5-dihydrodiol, 222 Pyrethroids, 170
Pyridine, 35, 40, 42–43, 44 Pyrolysis GC-MS, 66 Pyrrole, 44
Quadrupole instruments, 15–16, 289
Quaternary ammonium salts, 44 Quinol, 273, 275, 279
1,4-Quinol, 2,6-di-isopropyl, 270, 273
Quinoline, 44 Quinone, 79
Remifentanil, 267, 277 Residue analysis, 441–454 Resorcyl acid lactones, 461 Ropivacaine, 278
Rose oxide, 417 Sabinene, 417, 493
hydrate, 489
Sector instruments, 13–15, 289 Semtex, 392–393
Sesquiterpenes, 416, 431, 487–
488
oxygenated, 489–490 Sevoflurane, 235–240 Simazine, 171, 179 Simetryne, 49–50 Sinensal, 428
Sitostanol, 300
Solid-phase extraction, 202, 251, 343, 357, 372
Solid-phase micro-extraction, 229–
245, 251, 358, 372, 411 Somatotropins, 469
Soxhlet extraction, 202 Stanozolol, 457, 460 Steam distillation, 411
and extraction, 411, 490 Stearic acid, 298
Sterane, 60–66
Steroids, 60–66, 296–300, 309–
337, 445–448, 456–469 anabolic, 445, 456–466 sulphate, 3β-hydroxy-5-ene,
313 Sterol, 61
Stigmasterol, 315–316 Stilbene, 461
Styrene, 473 Sufentanil, 267, 273
Supercritical fluid extraction, 88–
89, 202, 411 Surface ionization, 31–54 Systematic toxicological analysis,
359–363 Tapazole, 471 Temazepam, 275, 381 Terpanes, 61–62, 66 Terpenes
mono-, 411, 416, 432, 438, 483–493
sesqui-, 416, 431, 483–493 Terpenoids, 45
Terphenyl, polychlorinated, 117–
119, 125–127, 137–138, 143–145
Terpinen-4-ol, 417 Terpinene, 420