Mass spectrometry of the cannabinoids and their metabolites
1987; Wiley; Volume: 6; Issue: 1 Linguagem: Inglês
10.1002/mas.1280060104
ISSN1098-2787
Autores Tópico(s)Psychedelics and Drug Studies
ResumoMass Spectrometry ReviewsVolume 6, Issue 1 p. 135-229 Article Mass spectrometry of the cannabinoids and their metabolites D. J. Harvey, D. J. Harvey University Department of Pharmacology, South Parks Road, Oxford, OX1 3QT, United KingdomSearch for more papers by this author D. J. Harvey, D. J. Harvey University Department of Pharmacology, South Parks Road, Oxford, OX1 3QT, United KingdomSearch for more papers by this author First published: Spring 1987 https://doi.org/10.1002/mas.1280060104Citations: 41AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL References 1 Turner, C. E.; ElSohly, M. A.; Boeren, E. G., J. Nat. Prods. 1980, 43, 169– 234. 2 Mechoulam, R., “ Marijuana: Chemistry, Pharmacology, Metabolism and Clinical Effects”; Academic Press: New York, 1973. 3 Nahas, G. G., “ Marihuana in Science and Medicine”; Raven Press: New York, 1984. 4 Fishbein, L., “ Chromatography of Environmental Hazards,” Vol. 4, Drugs of Abuse; Elsevier: Amsterdam, 1982; pp. 395– 423. 5 Paris, M.; Nahas, G. G., In “ Marihuana in Science and Medicine,” G. G. Nahas, Ed.; Raven Press: New York, 1984; pp. 3– 36. 6 Clarke, R. C., “ Marijuana Botany”; And/Or Press: Berkeley, CA, 1981. 7 Gaoni, Y.; Mechoulam, R., J. Am. Chem. Soc. 1964, 86, 1646– 1647. 8 Kreuz, D. S.; Axelrod, J., Science 1973, 179, 391– 393. 9 R. E. Willette, (Ed.) “ Cannabinoid Assays in Humans,” NIDA Res. Monogr. Ser., No. 7, NIDA: Rockville, MD, 1976. 10 J. A. Vinson, (Ed.) “ Cannabinoid Analysis in Physiological Fluids,” ACS Symp. Ser., No. 98, American Chemical Society, 1979. 11 R. L. Hawks, (Ed.) “ The Analysis of Cannabinoids in Biological Fluids,” NIDA Res. Monogr. Ser., No. 42, NIDA: Rockville, MD, 1982. 12 Harvey, D. J., Rev. Biochem. Toxicol 1984, 6, 221– 264. 13 Garrett, E. R.; Hunt, C. A., J. Pharm. Sci. 1977, 66, 395– 407. 14 Leuschner, J. T. A.; Harvey, D. J.; Bullingham, R. E. S.; Paton, W. D. M., Drug Metab. Dispos. 1986, 14, 230– 238. 15 Litterst, C. L.; Flora, K. P.; Cradock, J. C., Res. Commun. Subst. Abuse. 1982, 3, 453– 465. 16 Agurell, S.; Gillespie, H.; Halldin, M.; Hollister, L. E.; Johansson, E.; Lindgren, J. E.; Ohlsson, A.; Szirmai, M.; Widman, M., In “ Marihuana '84; Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985; pp. 49– 62. 17 Williams, P. L.; Moffat, A. C., J. Pharm. Pharmacol. 1980, 32, 445– 448. 18 Vree, T. B., J. Pharm. Sci. 1977, 66, 1444– 1450. 19 Gudzinowicz, B. J.; Gudzinowicz, M. J., “ Analysis of Drugs and Metabolites by Gas Chromatography-Mass Spectrometry,” Marcel Dekker: New York, 1980. 20 Gudzinowicz, B. J.; Gudzinowicz, M. J.; Hologgitas, J.; Driscoll, J. L. Adv. Chromatogr. 1980, 18, 197– 265. 21 Foltz, R. L., Adv. Anal. Toxicol. 1984, 1, 125– 157. 22 Harvey, D. J., In “ Marihuana in Science and Medicine,” G. G. Nahas, Ed.; Raven Press: New York, 1984, pp. 37– 107. 23 Harvey, D. J., In “ Analytical Methods in Human Toxicology,” Part 1, A. S. Curry, Ed.; McMillan Press: London, 1984, pp. 257– 310. 24 Harvey, D. J., In “ Marihuana '84: Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985, pp. 121– 136. 25 Claussen, U.; Fehlhaber, H.-W.; Korte, F., Tetrahedron 1966, 22, 3535– 3543. 26 Harvey, D. J., J. Chromatogr. 1978, 147, 291– 298. 27 Harvey, D. J., Biomed. Mass Spectrom. 1981, 8, 575– 578. 28 Terlouw, J. K.; Heerma, W.; Burgers, P. C.; Dijkstra, G.; Boon, A.; Kramer, H. F.; Salemink, C. A., Tetrahedron 1974, 30, 4243– 4248. 29 Budzikiewicz, H.; Aplin, R. T.; Lightner, D. A.; Djerassi, C.; Mechoulam, R.; Gaoni, Y., Tetrahedron 1965, 21, 1881– 1888. 30 Vree, T. B.; Nibbering, N. M. M., Tetrahedron 1973, 29, 3849– 3852. 31 Boeren, E. G.; Heerrna, W.; Terlouw, J. K., Org. Mass Spectrom. 1976, 11, 659– 663. 32 Harvey, D. J., Biomed. Mass Spectrom. 1977, 4, 265– 274. 33 Nilsson, J. L. G.; Nilsson, I. M.; Agurell, S.; Akermark, B.; Lagerlund, I., Acta Chem. Scand. 1971, 25, 768– 769. 34 Smith, R. M.; Kempfert, K. D., Phytochemistry 1977, 16, 1088– 1089. 35 Uliss, D. B.; Dalzell, H. C.; Handrick, G. R.; Howes, J. F.; Razdan, R. K., J. Med. Chem. 1975, 18, 213– 215. 36 Uliss, D. B.; Razdan, R. K.; Dalzell, H. C.; Handrick, G. R., Tetrahedron 1977, 33, 2055– 2059. 37 Bercht, C. A. L.; Lousberg, R. J. J. Ch.; Kuppers, F. J. E. M.; Salemink, C. A.; Vree, T. B.; Van Rossum, J. M., J. Chromatogr. 1973, 81, 163– 166. 38 Claussen, U.; Korte, F., Tetrahedron 1966, Suppl. 7, 89– 96. 39 Shoyama, Y.; Kuboe, K.; Nishioka, I.; Yamauchi, T., Chem. Pharm. Bull. (Tokyo) 1972, 20, 2072. 40 Turner, C. E.; Hadley, K., J. Pharm. Sci. 1973, 62, 251– 255. 41 Turner, C. E.; Hadley, K., J. Pharm. Sci., 1973, 62, 1083– 1086. 42 Lousberg, R. J. J. Ch,.; Bercht, C. A. L.; Van Coyen, R.; Spronck, H. J. W., Phytochemistry 1977, 16, 595– 597. 43 Van Ginneken, C. A. M.; Vree, T. B.; Breimer, D. D.; Van Rossum, J. M., In “ Proc. International Symposium on GC/MS,” Elba, Tamburini Publisher: Milan, 1972; pp. 18– 20. 44 Claussen, U.; Von Spulak, F.; Korte, F., Tetrahedron 1966, 22, 1477– 1479. 45 Claussen, U.; Von Spulak, F.; Korte, F., Tetrahedron 1968, 24, 1021– 1023. 46 Turner, C. E.; Hadley, K.; Henry, J.; Mole, M. L., J. Pharm. Sci. 1974, 63, 1872– 1876. 47 Yamauchi, T.; Shoyama, Y.; Matsuo, Y.; Nishioka, I., Chem. Pharm. Bull. (Tokyo) 1968, 16, 1164– 1165. 48 Friedrich-Fiechtl, J.; Spiteller, G., Tetrahedron 1975, 31, 479– 487. 49 Grote, H.; Spiteller, G., Tetrahedron 1978, 34, 3207– 3213. 50 Chan, W. R.; Magnus, K. E.; Watson, H. A., Experientia 1976, 32, 283– 284. 51 ElSohly, M. A.; El-Feraly, F. S.; Turner, C. E., Lloydia 1977, 40, 275– 280. 52 Turner, C. E.; ElSohly, M. A., J. Heterocyclic Chem. 1979, 16, 1667– 1668. 53 Harvey, D. J., In “ Marihuana '84: Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985; pp. 23– 30. 54 ElSohly, M. A.; Boeren, E. G.; Turner, C. E., Exterientia 1978, 34, 1127– 1128. 55 Boeren, E. G.; ElSohly, M. A.; Turner, C. E., Experientia 1979, 35, 1278– 1279. 56 ElSohly, H. N.; Boeren, E. G.; Turner, C. E.; ElSohly, M. A., In “ The Cannabinoids: Chemical, Pharmacologic and Therapeutic Aspects,” S. Agurell; W. L. Dewey; R. E. Willette, Eds.; Academic Press: Orlando, 1984; pp. 89– 96. 57 von Spulak, F.; Claussen, U.; Fehlhaber, H.-W.; Korte, F., Tetrahedron 1968, 24, 5379– 5383. 58 Krejci, Z.; Santavy, F., Acta Univ. Palackianea Olomuc 1955, 6, 59. 59 Mechoulam, R.; Gaoni, Y.;, Tetrahedron 1965, 21, 1223– 1229. 60 Mechoulam, R.; Ben-Zvi, Z.; Yagnitinsky, B.; Shani, A., Tetrahedron Lett. 1969, 2339– 2341. 61 Billets, S.; El-Feraly, F.; Fetterman, P. S.; Turner, C. E., Org. Mass Spectrom. 1976, 11, 741– 751. 62 Harvey, D. J., Biomed. Mass Spectrom. 1977, 4, 88– 93. 63 Paris, M.; Ghirlanda, C.; Chaigneau, M.; Giry, L., Compt. Rendus. C 1973, 276, 205– 207. 64 Bjorkman, S., J. Chromatogr. 1982, 237, 389– 397. 65 Shoyama, Y.,; Oku, R.; Yamauchi, T.; Nishioka, I., Chem. Pharm. Bull. (Tokyo) 1972 20, 1927– 1930. 66 Shani, A.; Mechoulam, R., Chem. Commun. 1970, 273– 274. 67 Shani, A.; Mechoulam, R., Tetrahedron 1974, 30, 2437– 2446. 68 Grote, H.; Spiteller, G., J. Chromatogr. 1978, 154, 13– 23. 69 Shoyama, Y.; Hirano, H.; Nishioka, I., Phytochemistry 1984, 23, 1909– 1912. 70 Shoyama, Y.; Hirano, H.; Makino, N.; Umekita, N.; Nishioka, I., Chem. Pharm. Bull. (Tokyo) 1977, 25, 2306– 2311. 71 Vollner, L.; Bieniek, D.; Korte, F., Tetrahedron Lett. 1969, 145– 147. 72 Stromberg, L., J. Chromatogr. 1974, 96, 179– 187. 73 Hendricks, H.; Batterman, S.; Bos, R.; Huizing, H. J.; Malingre, Th. M., J. Chromatogr. 1981, 205, 444– 450. 74 Gill, E. W., J. Chem. Soc. C, 1971, 579– 582. 75 Mercus, F. W. H. M., Nature (London) 1971, 232, 579– 580. 76 Fetterman, P. S.; Turner, C. E., J. Pharm. Sci. 1972, 61, 1476– 1477. 77 Vree, T. B.; Breimer, D. D.; Van Ginneken, C. A. M.; Van Rossum, J. M.; DeZeeuw, R. A.; Witte, A. H., Clin. Chem. Acta 1971, 34, 365– 372. 78 Vree, T. B.; Breimer, D. D.; Van Ginneken, C. A. M.; Van Rossum, J. M., J. Chromatogr. 1972, 74, 124– 127. 79 DeZeeuw, R. A.; Vree, T. B.; Breimer, D. D.; Van Ginneken, C. A. M., Experientia 1973, 29, 260– 261. 80 Shoyama, Y.; Hirano, H.; Oda, M.; Somehara, T.; Nishioka, I., Chem. Pharm. Bull. (Tokyo) 1975, 23, 1894– 1895. 81 Vree, T. B.; Breimer, D. D.; Van Ginneken, C. A. M.; Van Rossum, J. M., J. Pharm. Pharmacol. 1972, 24, 7– 12. 82 Turner, C. E.; Bouwsma, O. J.; Billets, S.; ElSohly, M. A., Biomed. Mass Spectrom. 1980, 7, 247– 256. 83 Harvey, D. J., J. Pharmacol. 1976, 28, 280– 285. 84 Mole, M. L., Jr.; Turner, C. E., J. Pharm. Sci. 1974, 63, 154– 156. 85 Petrzilka, T.; Haefliger, W.; Sikemeier, C., Helv. Chim. Acta 1969, 52, 1102– 1134. 86 Burstein, S. H.; Menezes, F.; Williamson, E.; Mechoulam, R., Nature (London) 1970, 225, 87– 88. 87 Ben-Zvi, Z.; Mechoulam, R.; Burstein, S., J. Am. Chem. Soc. 1970, 92, 3468– 3469. 88 Foltz, R. L.; Fentiman, A. F., Jr.; Leighty, E. G.; Walter, J. L.; Drewes, H. R.; Schwartz, W. E.; Page, T. F., Jr.; Truitt, E. B., Jr., Science 1970, 168, 844– 845. 89 Wall, M. E.; Brine, D. R.; Brine, G. A.; Pitt, C. G.; Freudenthal, R. I.; Christensen, H. D., J. Am. Chem. Soc. 1970, 92, 3466– 3468. 90 Nilsson, I. M.; Agurell, S.; Nilsson, J. L. G.; Ohlsson, A.; Sandberg, F.; Wahlqvist, M., Science 1970, 168, 1228– 1229. 91 Wall, M. E., Ann. N. Y. Acad. Sci. 1971, 191, 23– 39. 92 Ben-Zvi, Z.; Mechoulam, R.; Edery, H.; Porath, G., Science 1971, 174, 951– 952. 93 Mikes, F.; Hofmann, A.; Waser, P. G., Biochem. Pharmacol. 1971, 20, 2469– 2476. 94 Wall, M.; Brine, D. R.; Pitt, C. G.; Perez-Reyes, M., J. Am. Chem. Soc. 1972, 94, 8579– 8581. 95 Ben-Zvi, Z.; Burstein, S.; Zikopoulos, J., J. Am. Chem. Soc., 1974, 63, 1173. 96 Maynard, D. E.; Gurney, O.; Pitcher, R. G.; Kierstead, R. W., Experientia. 1971, 27, 1154– 1155. 97 Fahrenholtz, K. F., J. Org. Chem. 1972, 27, 2204– 2207. 98 Burstein, S.; Martinez, J.; Rosenfeld, J.; Wittstruck, T., In “ Cannabis and its Derivatives,” W. D. M. Paton; J. Crown, Eds.; Oxford University Press: Oxford, 1972; pp. 39– 49. 99 Burstein, S.; Rosenfeld, J.; Wittstruck, T., Science 1972, 176, 422– 423. 100 Mechoulam, R.; Ben-Zvi, Z.; Agurell, S.; Nilsson, I. M.; Nilsson, J. L. G.; Edery, H.; Grunfeld, Y., Experientia 1973, 29, 1193– 1195. 101 Watanabe, K.; Yamamoto, I.; Oguri, K.; Yoshimura, H., Chem. Pharm. Bull. (Tokyo) 1980, 28, 2154– 2157. 102 Watanabe, K.; Yamamoto, I.; Oguri, K.; Yoshimura, H., J. Pharmacobio-Dyn. 1980 3, 686. 103 Ben-Zvi, Z.; Burstein, S., Res. Commun. Chem. Pathol. Pharmacol. 1974, 8, 223– 229. 104 Ben-Zvi, Z.; Bergen, J. R.; Burstein, S., Res. Commun. Chem. Pathol. Pharmacol. 1974 9, 201– 204. 105 Ben-Zvi, Z.; Bergen, J. R.; Burstein, S.; Sehgal, P. K.; Varanelli, C., In “ The Pharmacology of Marihuana,” M. C. Braude; S. Szara, Eds.; Raven Press: New York, 1976, pp. 63– 75. 106 Widman, M.; Nordqvist, M.; Agurell, S.; Lindgren, J.-E.; Sandberg, F., Biochem. Pharmacol. 1974, 23, 1163– 1172. 107 Jones, G.; Widman, M.; Agurell, S.; Lindgren, J.-E., Acta Pharm. Suecica 1974, 11, 283– 294. 108 Nilsson, I. M.; Agurell, S.; Nilsson, J. L. G.; Ohlsson, A.; Lindgren, J.-E.; Mechoulam, R., Acta Pharm. Suecica 1973, 10, 97– 106. 109 Nordqvist, M.; Agurell, S.; Binder, M.; Nilsson, I. M., J. Pharm. Pharmacol. 1974, 26, 471– 473. 110 Nordqvist, M.; Lindgren, J.-E.; Agurell, S., J. Pharm. Pharmacol 1979, 31, 231– 237. 111 Nordqvist, M.; Agurell, S.; Rydberg, M.; Falk, L.; Ryman, T., J. Pharm. Pharmacol. 1979, 31, 238– 243. 112 Agurell, S.; Edward, C.; Halldin, M.; Leander, K.; Levy, S.; Lindgren, J.-E.; Mechoulam, R.; Nordqvist, M.; Ohlsson, A., Drug Metab. Dispos. 1979, 7, 155– 161. 113 Halldin, M. M.; Carlsson, S.; Kanter, S. L.; Widman, M.; Agurell, S., Arzneim Forsch. 1982, 32, 764– 768. 114 Halldin, M. M.; Andersson, L. K. R.; Widman, M.; Hollister, L. E., Arzneim-Forsch. 1982, 32, 1135– 1138. 115 Halldin, M. M.; Widman, M.; Agurell, S.; Hollister, L. E.; Kanter, S. L., In “ The Cannabinoids; Chemical, Pharmacologic and Therapeutic Aspects” S. Agurell; W. L. Dewey; R. E. Willette, Eds.; Academic Press: Orlando, 1984; pp. 211– 218. 116 Halldin, M. M.; Widman, M., Arzneim-Forsch. 1983, 33, 177. 117 Halldin, M. M.; Widman, M.; VonBahr, C.; Lindgren, J.-E.; Martin, B. R., Drug Metab. Dispos. 1982, 10, 297– 301. 118 Widman, M.; Nordqvist, M.; Dollery, C. T.; Briant, R. H., J. Pharm. Pharmacol. 1975, 27, 842– 848. 119 Halldin, M. M.,; Isaac, H.; Widman, M.; Nilsson, E.; Ryrfeldt, A., Xenobiotica 1984, 14, 277– 282, 120 Halldin, M.; Widman, M.; Martin, B., Acta Pharm. Suecica. 1979, 16, 34– 40. 121 Harvey, D. J.; Paton, W. D. M., In “ Marihuana: Chemistry, Biochemistry and Cellular Effects,” G. G. Nahas, Ed.; Springer: New York, 1976; pp. 93– 109. 122 Harvey, D. J.; Paton, W. D. M., Res. Commun. Chem. Pathol. Pharmacol. 1976, 13 585– 599. 123 Harvey, D. J.; Martin, B. R.; Paton, W. D. M., In “ Mass Spectrometry in Drug Metabolism” A. Frigerio; E. L. Ghisalberti, Eds.; Plenum: New York, 1977; pp. 403– 428. 124 Harvey, D. J.; Martin, B. R.; Paton, W. D. M., J. Pharm. Pharmacol. 1977, 29, 482– 486. 125 Harvey, D. J.; Paton, W. D. M., Res. Commun. Chem. Pathol. Pharmacol. 1978, 21, 435– 446. 126 Harvey, D. J.; Paton, W. D. M., Adv. Mass Spectrom. 1980, 8, 1194– 1203. 127 Powers, P.,; Wallington, M. J.; Hopkinson, J. A. V.; Kearns, G. L., Paper presented at the 23rd Annual Conference on Mass Spectrometry and Allied Topics, Houston, Texas, May, 25-30, 1975. ASMS, Abstracts; pp. 499– 502. 128 Harvey, D. J.; Paton, W. D. M., Proc. 7th Intl. Conf. Pharmacol., Pergamon Press: Oxford, 1978, Abstracts p. 455. 129 Kingston, D. G. I.; Holbrock, B. W.; Bursey, M. M.; Bursey, J. T., Chem. Rev. 1975, 75, 693– 730. 130 Quilliam, M. A.; Westmore, J. B., Steroids 1977, 29, 579– 611. 131 Diekman, J.; Thomson, J. B.; Djerassi, C., J. Org. Chem. 1967, 32, 3904– 3919. 132 Harvey, D. J., Biomed. Mass Spectrom. 1980, 7, 28– 34. 133 Harvey, D. J.; Paton, W. D. M., In “ Recent Developments in Mass Spectrometry in Biochemistry and Medicine,” Vol. 2, A. Frigerio, Ed.; Plenum Press: New York, 1979; pp. 127– 147. 134 Harvey, D. J.; Martin, B. R.; Paton, W. D. M., J. Pharm. Pharmacol. 1977, 29, 495– 497. 135 Martin, B. R.; Harvey, D. J.; Paton, W. D. M., J. Pharm. Pharmacol. 1976, 28, 773– 774. 136 Harvey, D. J.; Martin, B. R.; Paton, W. D. M., J. Pharm. Pharmacol. 1980, 32, 267– 271. 137 Yamamoto, I.; Narimatsu, S.; Shimonishi, T.; Watanabe, K.; Yoshimura, H., In “ Marihuana '84: Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985; pp. 107– 114. 138 Burstein, S.; Shoupe, T. S., Drug Metab. Dispos. 1981, 9, 94– 96. 139 Harvey, D. J.; Leuschner, J. T. A., Paton, W. D. M., Res. Commun. Subst. Abuse. 1980, 1, 159– 167. 140 Harvey, D. J.; Paton, W. D. M., J. Pharm. Pharmacol. 1977, 29, 498– 500. 141 Harvey, D. J.; Paton, W. D. M., Res. Commun. Subst. Abuse 1981, 2, 193– 201. 142 Inayama, S.; Sawa, A.; Hosoya, E., Chem. Pharm. Bull. (Tokyo). 1976, 24, 2209– 2218. 143 ApSimon, J. W.; Collier, T. L.; Guiver, M. D., Can. J. Chem. 1982, 60, 2804. 144 Handrick, G. R.; Uliss, D. B.; Dalzell, H. C.; Razdan, R. K., Tetrahedron Lett. 1979, 681– 684. 145 Harvey, D. J., Biomed. Mass Spectrom. 1981, 8, 579– 588. 146 Binder, M.; Agurell, S.; Lindgren, J.-E., Helv. Chim. Acta. 1974, 57, 1626– 1641. 147 Wall, M. E.; Brine, D. R., In “ Marihuana: Chemistry, Biochemistry and Cellular Effects,” G. G. Nahas, Ed.; Springer: New York, 1976; pp. 51– 62. 148 Binder, M., In “ Marihuana: Chemistry, Biochemistry and Cellular Effects,” G. G. Nahas, Ed.; Springer: New York, 1976; pp. 159– 168. 149 Uliss, D. B.; Razdan, R. K.; Dalzell, H. C., J. Am. Chem. Soc. 1974, 96, 7372– 7374. 150 Duffley, R. P.; Lambert, G.; Dalzell, H. C.; Razdan, R. K., Experientia, 1981, 37, 931– 932. 151 Harvey, D. J.; Leuschner, J. T. A., Drug Metab. Dispos., 1985, 13, 215– 219. 152 Rickards, R. W.; Watson, W. P., J. Org. Chem., 1980, 45, 751– 752. 153 Harvey, D. J.; Paton, W. D. M., Drug Metab. Dispos., 1980, 8, 178– 186. 154 Frank, I.; Binder, M., Helv. Chim. Acta., 1980, 63, 2508– 2514. 155 Harvey, D. J.; Gill, E. W.; Slater, M. Paton, W. D. M., Drug Metab. Dispos. 1980 8, 439– 445. 156 Binder, M.; Barlage, U., Helv. Chim. Acta. 1980, 63, 255– 267. 157 Petrzilka, T.; Demuth, M., Helv. Chim. Acta. 1974, 57, 121– 150. 158 Harvey, D. J., Xenobiotica 1985, 15, 187– 197. 159 Gurney, O.; Maynard, D. E.; Pitcher, R. G.; Kierstead, R. W., J. Am. Chem. Soc. 1972, 94, 7928– 7929. 160 Mechoulam, R.; Varconi, H.; Ben-Zvi, Z.; Edery, H.; Grunfeld, Y., J. Am. Chem. Soc. 1972, 94, 7930– 7931. 161 Ben-Zvi, Z.; Burstein, S., Biochem. Pharmacol. 1975, 24, 1130– 1131. 162 Burstein, S. In “ Cannabinoid Analysis in Physiological Fluids,” ACS Symposium Series, No. 98, J. A. Vinson, Ed.; Am. Chem. Soc., 1979; pp. 1– 12. 163 Narimatsu, S.; Yamamoto, I.; Watanabe, K.; Yoshimura, H., J. Pharmacobio-Dyn. 1983, 6, 558– 564. 164 Ohlsson, A.; Emanuelson, I., Acta Pharm. Suecica. 1979, 16, 396– 407. 165 Ben-Zvi, Z., Xenobiotica 1980, 10, 805– 809. 166 Narimatsu, S.; Watanabe, K.; Yamamoto, I.; Yoshimura, H., J. Pharmacobio-Dyn. 1982, 5, S– 58. 167 Narimatsu, S.; Watanabe, K.; Yamamoto, I.; Yoshimura, H., Xenobiotica 1982, 12, 561– 565. 168 Yamamoto, I.; Narimatsu, S.; Watanabe, K.; Yoshimura, H., Biochem. Biophys. Res. Commun. 1982, 109, 922– 926. 169 Yamamoto, I.; Narimatsu, S.; Watanabe, K.; Yoshimonishi, T.; Yoshimura, H.; Nagano, T., Chem. Pharm. Bull. 1983, 31, 1784– 1787. 170 Yagen, B.; Levy, S.; Mechoulam, R.; Ben-Zvi, Z., J. Am. Chem. Soc., 1977, 99, 6444– 6446. 171 Levy, S.; Yagen, B.; Mechoulam, R., Science 1978, 200, 1391– 1392. 172 Lyle, M. A.; Pallante, S.; Head, K.; Fenselau, C., Biomed. Mass Spectrom. 1977, 4, 190– 196. 173 Pallante, S.; Lyle, M. A.; Fenselau, C., Drug Metab. Dispos. 1978, 6, 389– 395. 174 Harvey, D. J., Biomed. Mass Spectrom. 1977, 4, 364– 370. 175 Leighty, E. G.; Fentiman, A. F., Jr; Foltz, R. L., Res. Commun. Chem. Pathol. Pharmacol. 1976, 14, 13– 28. 176 Binder, M., Helv. Chim. Acta. 1976, 59, 1674– 1684. 177 Robertson, L. W.; Lyle, M. A.; Billets, S., Biomed. Mass Spectrom. 1975, 2, 266– 271. 178 Christie, R. M.; Rickards, R. W.; Watson, W. P., Aust. J. Chem. 1978, 21, 1799– 1807. 179 Robertson, L. W.; Koh, S.-W.; Huff, R. K.; Malhotra, R. K.; Ghosh, A., Experientia 1978, 34, 1020– 1022. 180 Robertson, L. W.; Huff, S. R.; Ghosh, A.; Malhotra, R., Lloydia 1978, 41, 659. 181 Abbott, B. J.; Fukuda, D. S.; Archer, R. A., Experientia 1977, 33, 718– 720. 182 Vidic, H.-J.; Hoyer, G.-A.; Kieslich, K.; Rosenberg, D., Chem. Ber. 1976, 109, 3606– 3614. 183 Nilsson, I.; Agurell, S.; Nilsson, J. L. G.; Widman, M.; Leander, K., J. Pharm. Pharmacol. 1973, 25, 486– 487. 184 Martin, B.; Nordqvist, M.; Agurell, S.; Lindgren, J.-E.; Leander, K.; Binder, M., J. Pharm. Pharmacol. 1976, 28, 275– 379. 185 Martin, B.; Agurell, S.; Nordqvist, M.; Lindgren, J.-E., J. Pharm. Pharmacol. 1976, 28, 603– 608. 186 Martin, B. R.; Harvey, D. J.; Paton, W. D. M., Drug Metab. Dispos. 1977, 5, 259– 267. 187 Harvey, D. J.; Martin, B. R., Paton, W. D. M., In “ Recent Developments in Mass Spectrometry in Biochemistry and Medicine,” Vol. 1, A. Frigerio, Ed.; Plenum Press: New York, 1978; pp. 161– 184. 188 Harvey, D. J.; Martin, B. R.; Paton, W. D. M., Biochem. Pharmacol. 1976, 25, 2217– 2219. 189 Harvey, D. J.; Martin, B. R.; Paton, W. D. M., Res. Commun. Chem. Pathol. Pharmacol. 1977, 16, 265– 279. 190 Widman, M.; Nilsson, I. M.; Nilsson, J. L. G.; Agurell, S.; Leander, K., Life Sci. 1971, 10 (2), 157– 162. 191 Yisak, W.-A.; Widman, M.; Lindgren, J.-E.; Agurell, S., J. Pharm. Pharmacol. 1977, 29, 487– 490. 192 Widman, M.; Dahmen, J.; Leander, K., Petersson, K., Acta Pharm. Suec. 1975, 12, 385– 392. 193 Fonseka, K.; Widman, M., J. Pharm. Pharmacol. 1977, 29, 12– 14. 194 Yisak, W.-A.; Widman, M.; Agurell, S., J. Pharm. Pharmacol. 1978, 30, 554– 557. 195 Yisak, W.; Agurell, S.; Lindgren, J.-E.; Widman, M., J. Pharm. Pharmacol. 1978, 30, 462– 463. 196 Harvey, D. J., Biomed. Mass Spectrom. 1981, 8, 366– 372. 197 Petrzilka, T.; Prasad, K. K.; Schmid, G., Helv. Chim. Acta. 1976, 59, 1963-1968. 198 Razdan, R. K.; Uliss, D. B.; Dalzell, H. C., J. Am. Chem. Soc. 1973, 95, 2361– 2362. 199 Harvey, D. J.; Paton, W. D. M., J. Chromatogr. 1975, 109, 73– 80. 200 Harvey, D. J., Org. Mass Spectrom. 1977, 12, 473– 474. 201 Knaus, E. E.; Coutts, R. T.; Kazakoff, C. W., J. Chromatogr. Sci. 1976, 14, 525– 530. 202 Harvey, D. J., Biomed. Mass Spectrom. 1980, 7, 211– 216. 203 Harvey, D. J., In “ Recent Developments in Mass Spectrometry in Biochemistry, Medicine and Environmental Research, 7”, A. Frigerio, Ed.; Elsevier: Amsterdam, 1981; pp. 315– 325. 204 Harvey, D. J., Biomed. Mass Spectrom., 1980, 7, 278– 283. 205 Foltz, R. L.; McGinnis, K. M.; Chin, D. M., Biomed. Mass Spectrom. 1983, 10, 316– 323. 206 Garrett, E. R.; Hunt, C. A., J. Pharm. Sci. 1974, 63, 1056– 1064. 207 Garrett, E. R.; Gouyette, A. J.; Hunt, C. A., In “ Cannabinoid Analysis in Physiological Fluids,” J. A. Vinson;, Ed.; ACS Symp. Ser., No. 98, 1979; pp. 13– 37. 208 Garrett, E. R.; Tsau, J., J. Pharm. Sci. 1974, 63, 1563– 1574. 209 Garrett, E. R.; Gouyette, A. J.; Roseboom, H., J. Pharm. Sci. 1978, 67, 27– 32. 210 Garrett, E. R., In “ Marihuana: Biological Effects” G. G. Nahas; W. D. M. Paton, Eds.; Pergamon Press: Oxford, 1979, pp. 105– 121. 211 Agurell, S.; Gustafsson, B.; Holmstedt, B.; Leander, K.; Lindgren, J.-E.; Nilsson, I.; Sandberg, F.; Asberg, M., J. Pharm. Pharmacol. 1973, 25, 554– 558. 212 Agurell, S.; Levander, S.; Binder, M.; Bader-Bartfai, A. Gustafsson, B. Leander, K.; Lindgren, J.-E.; Ohlsson, A.; Tobisson, B., In “ Pharmacology of Marijuana” M. C. Braude; S. Szara, Eds.; Raven Press: New York, 1974; pp. 49– 61. 213 Ohlsson, A.; Lindgren, J.-E.; Leander, K.; Agurell, S., In “ Cannabinoid Assays in Humans,” Res. Monogr. Ser., No. 7., R. E. Willette, Ed.; NIDA: Rockville, 1976; pp. 48– 63. 214 Ohlsson, A.; Lindgren, J.-E.; Leander, K.; Agurell, S.;, In “ Mass Spectrometry in Drug Metabolism” A. Frigerio; E. L. Ghisalberti Eds.; Plenum Press: New York, 1976; pp. 429– 440. 215 Agurell, S.; Lindgren, J.-E.; Ohlsson, A., In “ Marihuana: Biological Effects” G. G. Nahas; W. D. M. Paton, Eds.; Pergamon Press: Oxford, 1979; pp. 3– 13. 216 Ohlsson, A.; Agurell, S.; Lindgren, J.-E.; Leander, K., In “ Cannabinoid Analysis in Physiological Fluids,” J. A. Vinson, Ed.; ACS Symp. Ser., No. 98, 1979; pp. 73– 79. 217 Harvey, D. J.; Martin, B. R.; Paton, W. D. M., In “ Marihuana: Biological Effects” G. G. Nahas; W. D. M. Paton, Eds.; Pergamon Press: Oxford, 1979; pp. 45– 62. 218 Ohlsson, A.; Lindgren, J.-E.; Wahlen, A.; Agurell, S.; Hollister, L. E.; Gillespie, H. K., Biomed. Mass Spectrom. 1982, 9, 6– 10. 219 Agurell, S.; Carlsson, S.; Lindgren, J.-E.; Ohlsson, A.; Gillespie, H.; Hollister, L., Experientia 1981, 37, 1090– 1092. 220 Ohlsson, A.; Lindgren, J.-E.,; Gillespie, H.; Hollister, L. E., In “ The Cannabinoids; Chemical, Pharmacologic and Therapeutic Aspects” S. Agurell; W. L. Dewey; R. E. Willette, Eds.; Academic Press: Orlando, 1984; pp. 219– 225. 221 Ohlsson, A.; Johansson, E.; Lindgren, J.-E.; Agurell, S.; Gillespie, H.; Hollister, L. E., In “ Marihuana '84: Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985; pp. 63– 68. 222 Wall, M. E.; Harvey, T. M.; Bursey, J. T.; Brine, D. R.; Rosenthal, D., In “ Cannabinoid Assays in Humans,” Res. Monogr. Ser., No. 7., R. E. Willette, Ed.; NIDA: Rockville, 1976; pp. 107– 117. 223 Rosenthal, D.; Harvey, T. M.; Bursey, J. T.; Brine, D. R.; Wall, M. E., Biomed. Mass Spectrom. 1978, 5, 312– 316. 224 Wall, M. E.; Brine, D. R.; Bursey, J. T.; Rosenthal, D., In “ Cannabinoid Analysis in Physiological Fluids,” J. A. Vinson, Ed.; ACS Symp. Ser., No. 98, 1979; pp. 39– 57. 225 Ohlsson, A.; Lindgren, J.-E.; Wahlen, A.; Agurell, S.; Hollister, L. E.; Gillespie, H. K., Clin. Pharmacol. Ther. 1980, 28, 409– 416. 226 Lindgren, J.-E.; Ohlsson, A.; Agurell, S.; Hollister, L.; Gillespie, H., Psychopharmacol. 1981, 74, 208– 212. 227 Wall, M. E.; Brine, D. R., In “ Marihuana: Biological Effects” G. G. Nahas; W. D. M. Paton, Eds.; Pergamon: Oxford, 1979; pp. 15– 43. 228 Wall, M. E.; Perez-Reyes, M., J. Clin, Pharmacol. 1981, 21, 178s– 189s. 229 Bergman, R. A.; Lukaszewski, T.; Wang, Y. S. S., J. Anal. Toxicol. 1981, 5, 85– 89. 230 Rosenfeld, J. J.; Bowins, B.; Roberts, J.; Perkins, J.; MacPherson, A. S., Anal. Chem. 1974, 46, 2232– 2234. 231 Rosenfeld, J. M.; Taguchi, V. Y., Anal. Chem. 1976, 48, 726– 729. 232 Rosenfeld, J., Anal. Lett. 1977, 10, 917– 930. 233 Rosenfeld, J., In “ Cannabinoid Analysis in Physiological Fluids,” J. A. Vinson, Ed.; ACS Symp. Ser., No. 98, 1979; pp. 81– 91. 234 Detrick, R.; Foltz, R., In “ Cannabinoid Assays in Humans,” Res. Monogr. Ser., No. 7., R. E. Willette, Ed.; NIDA: Rockville, 1976; pp. 88– 95. 235 Foltz, F. L.; Clarke, P. A.; Hidy, B. J.; Lin, D. C. K.,; Graffeo, A. P.; Petersen, B. A., In “ Cannabinoid Analysis in Physiological Fluids,” J. A. Vinson, Ed.; ACS Symp. Ser., No. 98, 1979; pp. 59– 71. 236 Foltz, R. L.; Hidy, B. J., In “ The Analysis of Cannabinoids in Biological Fluids,” Res. Monogr. Ser., No. 42, R. L. Hawks, Ed., NIDA: Rockville, 1982; pp. 99– 118. 237 Karlsson, L.; Jonsson, J.; Aberg, K.; Roos, C., J. Anal. Toxicol. 1983, 7, 198– 202. 238 Hunt, D. F.; Crow, F. W., Anal. Chem. 1978, 50, 1781– 1784. 239 Harvey, D. J.; Leuschner, J. T. A.; Paton, W. D. M., J. Chromatogr. 1980, 202, 83– 92. 240 Harvey, D. J.; Leuschner, J. T. A.; Paton, W. D. M., Br. J. Pharmacol. 1981, 74, 771p. 241 Harvey, D. J.; Leuschner, J. T. A.; Paton, W. D. M., J. Chromatogr. 1982, 239, 243– 250. 242 Harvey, D. J.; Leuschner, J. T. A.; Wing, D. R.; Paton, W. D. M., In “ The Cannabinoids; Chemical, Pharmacologic and Therapeutic Aspects” S. Agurell; W. L. Dewey; R. E. Willette, Eds.; Academic Press: Orlando, 1984; pp. 291– 308. 243 Harvey, D. J.; Leuschner, J. T. A., Paton, W. D. M., In “ Marihuana '84: Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985; pp. 77– 84. 244 Leuschner, J. T. A.; Harvey, D. J.; Paton, W. D. M., In “ Marihuana '84: Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985; pp. 93– 100. 245 Leuschner, J. T. A.; Wing, D. R.; Harvey, D. J.; Brent, G. A.; Dempsey, C. E.; Watts, A.; Paton, W. D. M., Experientia 1984, 40, 866– 868. 246 Harvey, D. J.; Leuschner, J. T. A.; Paton, W. D. M., Spectroscopy Int. J. 1985, 3, 195– 209. 247 Valentine, J. L.; Bryant, P. J.; Gutshall, P. L.; Gan, O. H. M.; Lovegreen, P. D.; Thompson, E. D.; Niu, H. C., J. Pharm. Sci. 1977, 66, 1263– 1266. 248 Valentine, J. L.; Bryant, P. J.; Gutshall, P. L.; Gan, O. H. M., Niu, H. C., Anal. Lett. 1979, 12, 867– 880. 249 Manolis, A.; McBurney, L. J.; Bobbie, B. A., Clin. Biochem. 1983, 16, 229– 233. 250 Baker, P. B.; Phillips, G. F., Analyst 1983, 108, 777– 807. 251 Liu, J. H.; Fitzgerald, M. P.; Smith, G. V., Anal. Chem. 1979, 51, 1875– 1877. 252 Vree, T. B.; Breimer, D. D.; Van Ginneken, C. A. M.; Van Rossum, J. M., J. Chromatogr. 1972, 74, 209– 224. 253 Karasek, F. W., Anal. Chem. 1974, 46, 710A– 720A. 254 Karasek, F. W.; Karasek, D. E.; Kim, S. H., J. Chromatogr. 1975, 105, 345– 352. 255 Pirl, J. N.; Papa, V. M.; Spikes, J. J., J. Anal. Toxicol. 1979, 3, 129– 132. 256 Hattori, H.; Suzuki, O.; Asano, M., Koenshu-Iyo Masu Kenkyukai 1980, 5, 191– 194. ( Chem. Abs. 1981, 94, 131811D). 257 Semkin, E. M.; Shaposhnikov, A. V.; Galyashin, V. N.; Kuz'min, N. M., Farmatsiya (Moscow) 1980, 29, 41– 44. ( Chem. Abs. 1980, 93, 1974 03h). 258 Green, D. E., In “ Cannabinoid Assays in Humans,” Res. Monogr. Ser., No. 7., R. E. Willette, Ed.; NIDA: Rockville, 1976; pp. 70– 87. 259 Green, D. E.; Chao, F.-C.; Loeffler, K. O.; Kanter, S. L., In “ Cannabinoid Analysis in Physiological Fluids,” J. A. Vinson, Ed.; ACS Symp. Ser., No. 98, 1979; pp. 93– 113. 260 Nordqvist, M.; Lindgren, J.-E.; Agurell, S., In “ Cannabinoid Assays in Humans,” Res. Monogr. Ser., No. 7., R. E. Willette, Ed.; NIDA: Rockville, 1976; pp. 64– 69. 261 Nordqvist, M.; Lindgren, J.-E.; Agurell, S., In “ Mass Spectrometry in Drug Metabolism” A. Frigerio; E. L. Ghisalberti, Eds.; Plenum Press: New York, 1976; pp. 441– 448. 262 Kaistha, K. K.; Tadrus, R., J. Chromatogr. 1982, 237, 528– 533. 263 Nakamura, G. R.; Stall, W. J.; Folen, V. A.; Masters, R. G., J. Chromatogr. 1983, 264, 336– 338. 264 ElSohly, M. A.; ElSohly, H. N.; Stanford, D. F.; Evans, M. G.; Jones, A. B., In “ Marihuana '84: Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985; pp. 137– 146. 265 Jones, A. B.; ElSohly, H. N.; Arafat, E. S.; ElSohly, M. A., J. Anal. Toxicol. 1984 8. 266 Yeager, E. P.; Goebelsmann, U.; Soares, J. R.; Grant, J. D.; Gross, S. J., J. Anal. Toxicol. 1981, 5, 81– 84. 267 Williams, P. L.; Moffat, A. C.; King, L. J., J. Chromatogr. 1978, 155, 273– 283. 268 Moffat, A. C.; Williams, P. L.; King, L. J., In “ The Analysis of Cannabinoids in Biological Fluids,” Res. Monogr. Ser., No. 42, R. L. Hawks, Ed.; NIDA: Rockville, 1982; pp. 56– 68. 269 Williams, P. L.; Moffat, A. C.; King, L. J., J. Chromatogr. 1979, 186, 595– 603. 270 Law, B.; Pocock, K.; Moffat, A. C., J. Forensic, Sci. Soc. 1982, 22, 275– 281. 271 Peat, M. A.; Finkle, B. S.; Deyman, M. E., In “ The Analysis of Cannabinoids in Biological Fluids,” R. L. Hawks, Ed.; NIDA Res. Monogr., No. 42, NIDA: Rockville, 1982; pp. 85– 98. 272 Hanson, V. W.; Buonarati, M. H.; Baselt, R. C.; Wade, N. A.; Yep, C.; Biasotti, A. A.; Reeve, V. C.; Wong, A. S.; Orbanowsky, M. W., J. Anal. Toxicol. 1983, 7, 96– 102. 273 Law, B.; Moffat, A. C., In “ Marihuana, 84: Proceedings of the Oxford Symposium on Cannabis,” D. J. Harvey, Ed.; IRL Press: Oxford, 1985; pp. 197– 204. Citing Literature Volume6, Issue1Spring 1987Pages 135-229 ReferencesRelatedInformation
Referência(s)