Chemistry, metabolism, and toxicology of cannabis: Clinical implications

Iranian Journal of Psychiatry

Volumn 7, Issue 4, 2012, Pages 149-156

  Sharma, Priyamvada ^a   Murthy, Pratima ^a   Bharath, M M Srinivas ^a  

^a NATIONAL INSTITUTE OF MENTAL HEALTH AND NEUROSCIENCES   (India)

Author keywords

Cannabinoids; Cannabis; Mental disorders; Tetrahydrocannabinol

Indexed keywords

EID: 84877018249     PISSN: 17354587     EISSN: 20082215     Source Type: Journal    
DOI: None     Document Type: Article

References (88)

1. Brecher EM. The Consumers Union Report - Licit and Illicit Drugs. Little, Brown & Co 1972.
2. Balabanova S, Parsche F, Pirsig W. First identification of drugs in Egyptian mummies. Naturwissenschaften 1992; 79: 358.
3. Grotenhermen F. The toxicology of cannabis and cannabis prohibition. Chem Bio divers 2007; 4: 1744-1769.
4. Raharjo TJ, Verpoorte R. Methods for the analysis of cannabinoids in biological materials: a review. Phytochem Anal 2004; 15: 79-94.
5. Hazekamp A, Grotenhermen F. Review on Clinical Studies with Cannabis and Cannabinoids 2005-2009. Cannabinoids 2010; 5:1-21.
6. Miller PM, Plant M. Drinking, smoking, and illicit drug use among 15 and 16 year olds in the United Kingdom. BMJ 1996; 313: 394-397.
7. Hall WD. Cannabis use and the mental health of young people. Aust N Z J Psychiatry 2006; 40: 105-113.
8. Malhotra A, Parthasarathy B. Cannabis Use and Performance in Adolescents. J Indian Assoc Child AdolescMent Health 2006; 2:59-67.
9. Mechoulam R. Plant cannabinoids: a neglected pharmacological treasure trove. Br J Pharmacol 2005; 146: 913-915.
10. Appendino G, Chianese G and Taglialatela-Scafati O. Cannabinoids: occurrence and medicinal chemistry. Curr Med Chem 2011; 18: 1085-1099.
11. Perez-Reyes M, White WR, McDonald SA, Hicks RE, Jeffcoat AR and Cook CE. The pharmacologic effects of daily marijuana smoking in humans. Pharmacol Biochem Behav 1991; 40: 691-694.
12. Musshoff F, Madea B. Review of biologic matrices (urine, blood, hair) as indicators of recent or ongoing cannabis use. Ther Drug Monit 2006; 28: 155-163.
13. Skopp G, Potsch L. An investigation of the stability of free and glucuronidated 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid in authentic urine samples. J Anal Toxicol 2004; 28: 35-40.
14. Fenimore DC, Davis CM, Whitford JH, Harrington CA. Vapor phase silylation of laboratory glassware. Analytical Chemistry 1976;48: 2289-90.
15. Onaivi ES, Ishiguro H, Gong JP, Patel S, Perchuk A, Meozzi PA, et al. Discovery of the presence and functional expression of cannabinoid CB2 receptors in brain. Ann N Y Acad Sci 2006; 1074: 514-536.
16. Onaivi ES. Neuropsychobiological evidence for the functional presence and expression of cannabinoid CB2 receptors in the brain. Neuropsychobiology 2006; 54: 231-246.
17. Chaperon F, Thiebot MH. Behavioral effects of cannabinoid agents in animals. Crit Rev Neurobiol 1999; 13: 243-281.
18. Pertwee RG. Pharmacological actions of cannabinoids.Handb Exp Pharmacol 2005: 1-51.
19. Burstein S, Hunter SA, Sedor C, Shulman S. Prostaglandins and cannabis--IX. Stimulation of prostaglandin E2 synthesis in human lung fibroblasts by delta 1-tetrahydrocannabinol.BiochemPharmacol 1982; 31: 2361-2365.
20. Grotenhermen F. Pharmacokinetics and pharmacodynamics of cannabinoids. Clin Pharmacokinet 2003; 42: 327-360.
21. 21-Bloom AS. Effect of delta9-tetrahydrocannabinol on the synthesis of dopamine and norepinephrine in mouse brain synaptosomes.J Pharmacol ExpTher 1982; 221: 97-103.
22. Chakravarty I, Sheth AR and Ghosh JJ.Effect of acute delta9-tetrahydrocannabinol treatment on serum luteinizing hormone and prolactin levels in adult female rats.FertilSteril 1975; 26: 947-948.
23. Mendelson JH, Mello NK. Effects of marijuana on neuroendocrine hormones in human males and females.NIDA Res Monogr 1984; 44: 97-114.
24. Munro S, Thomas KL, Abu-Shaar M. Molecular characterization of a peripheral receptor for cannabinoids. Nature 1993; 365: 61-65.
25. Grotenhermen F. Cannabinoids. Curr Drug Targets CNS NeurolDisord 2005; 4: 507-530.
26. Adams IB and Martin BR. Cannabis: pharmacology and toxicology in animals and humans. Addiction 1996; 91: 1585-1614.
27. Herkenham M, Lynn AB, Little MD, Johnson MR, Melvin LS, de Costa BR, et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A 1990; 87: 1932-1936.
28. Gardner E, Lowinson JH. Marijuana's interaction with brain reward systems: update 1991. Pharmacol Biochem Behav 1991; 40: 571-580.
29. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 1992; 258: 1946-1949.
30. Gardner EL, Vorel SR. Cannabinoid transmission and reward-related events. Neurobiol Dis 1998; 5: 502-533.
31. Matsuda LA, Lolait SJ, Brownstein MJ, Young AC and Bonner TI. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 1990; 346: 561-564.
32. Howlett AC, Bidaut-Russell M, Devane WA, Melvin LS, Johnson MR, Herkenham M. The cannabinoid receptor: biochemical, anatomical and behavioral characterization. Trends Neurosci 1990; 13: 420-423.
33. Musty RE, Reggio P, Consroe P. A review of recent advances in cannabinoid research and the 1994 International Symposium on Cannabis and the Cannabinoids. Life Sci 1995; 56: 1933-1940.
34. Wickelgren I. Marijuana: harder than thought? Science 1997; 276: 1967-1968.
35. Ashton CH. Pharmacolgy and effect of cannabis:A brief review. Br J Psychiatry 2003;45:182-188.
36. Budney AJ, Hughes JR. The cannabis withdrawal syndrome. CurrOpin Psychiatry 2006; 19: 233-238.
37. Maykut MO. Health consequences of acute and chronic marihuana use. ProgNeuropsychopharmacol Biol Psychiatry 1985; 9: 209-238.
38. Jones RT. Cannabis tolerance and dependence. In. Fehr KO, Kalant H eds.Cannabis and Health Hazards. Toronto: Toronto Addiction Research Foundation; 1983.
39. Miller NS, Gold MS. The diagnosis of marijuana (cannabis) dependence. J Subst Abuse Treat 1989; 6: 183-192.
40. Jain R, Balhara YP. Neurobiology of cannabis addiction. Indian J Physiol Pharmacol 2008; 52: 217-232.
41. Haney M. The marijuana withdrawal syndrome: diagnosis and treatment. Curr Psychiatry Rep 2005; 7: 360-366.
42. Vandrey R, Budney AJ, Kamon JL, Stanger C. Cannabis withdrawal in adolescent treatment8. Malhotra A, Parthasarathy B. Cannabis Use and Performance in Adolescents. J Indian Assoc Child AdolescMent Health 2006; 2:59-67.
43. Hall W, Degenhardt L, Teesson M. Cannabis use and psychotic disorders: an update. Drug Alcohol Rev 2004; 23: 433-443.
44. Hall W, Degenhardt L, Teesson M. Cannabis use and psychotic disorders: an update. Drug Alcohol Rev 2004; 23: 433-443.
45. Kulhalli V, Isaac M and Murthy P. Cannabis-related psychosis: Presentation and effect of abstinence. Indian J Psychiatry 2007; 49: 256-261.
46. Leweke FM, Koethe D. Cannabbis and Psychiatric disoreder: it is not only addiction. Addiction Biol 2008;13:264-275.
47. Sewell RA, Skosnik PD, Garcia-Sosa I, Ranganathan M, D'Souza DC. [Behavioral, cognitive and psychophysiological effects of cannabinoids: relevance to psychosis and schizophrenia]. Rev Bras Psiquiatr 2010; 32 Suppl 1: S15-30.
48. Castle D, Murray R. Marijuana and madness, First edition. United Kingdom: Cambridge university press;2004.
49. McBurney LJ, Bobbie BA, Sepp LA. GC/MS and EMIT analyses for delta 9-tetrahydrocannabinol metabolites in plasma and urine of human subjects. J Anal Toxicol 1986; 10: 56-64.
50. Chiarotti M, Costamagna L. Analysis of 11-nor-9-carboxy-delta(9)-tetrahydrocannabinol in biological samples by gas chromatography tandem mass spectrometry (GC/MS-MS). Forensic SciInt 2000; 114: 1-6.
51. Vandevenne M, Vandenbussche H, Verstraete A. Detection time of drugs of abuse in urine. ActaClinBelg 2000; 55: 323-333.
52. Law B, Mason PA, Moffat AC, Gleadle RI, King LJ. Forensic aspects of the metabolism and excretion of cannabinoids following oral ingestion of cannabis resin. J Pharm Pharmacol 1984; 36: 289-294.
53. Owens SM, McBay AJ, Reisner HM, Perez-Reyes M. 125I radioimmunoassay of delta-9-tetrahydrocannabinol in blood and plasma with a solid-phase second-antibody separation method. Clin Chem 1981; 27: 619-624.
54. Wahlqvist M, Nilsson IM, Sandberg F, Agurell S. Binding of delta-1-tetrahydrocannabinol to human plasma proteins. Bio chem Pharmacol 1970; 19: 2579-2584.
55. Widman M, Agurell S, Ehrnebo M, Jones G. Binding of (+)- and (minus)-delta-1-tetrahydrocannabinols and (minus)-7-hydroxy-delta-1-tetrahydrocannabinol to blood cells and plasma proteins in man. J Pharm Pharmacol 1974; 26: 914-916.
56. Hollister LE, Gillespie HK, Ohlsson A, Lindgren JE, Wahlen A, Agurell S. Do plasma concentrations of delta 9-tetrahydrocannabinol reflect the degree of intoxication? J Clin Pharmacol 1981; 21: 171S-177S.
57. Huestis MA, Henningfield JE, Cone EJ. Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana. J Anal Toxicol 1992; 16:276-82.
58. Lemberger L, Axelrod J, Kopin IJ. Metabolism and disposition of delta-9-tetrahydrocannabinol in man. Pharmacol Rev 1971; 23: 371-380.
59. Karschner EL, Schwilke EW, Lowe RH, Darwin WD, Herning RI, Cadet JL, et al. Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers. J Anal Toxicol 2009; 33: 469-477.
60. Kogan NM, Mechoulam R. Cannabinoids in health and disease. Dialogues Clin Neurosci 2007; 9: 413-430.
61. Haggerty GC, Deskin R, Kurtz PJ, Fentiman AF, Leighty EG. The pharmacological activity of the fatty acid conjugate 11-palmitoyloxy-delta 9-tetrahydrocannabinol. Toxicol Appl Pharmacol 1986; 84: 599-606.
62. Musshoff F, Madea B. Review of biologic matrices (urine, blood, hair) as indicators of recent or ongoing cannabis use. Ther Drug Monit 2006; 28: 155-163.
63. Huestis MA. Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol. Handb Exp Pharmacol 2005: 657-690.
64. Smith-Kielland A, Skuterud B, Morland J. Urinary excretion of 11-nor-9-carboxy-delta9-tetrahydrocannabinol and cannabinoids in frequent and infrequent drug users. J Anal Toxicol 1999; 23: 323-332.
65. Reiter A, Hake J, Meissner C, Rohwer J, Friedrich HJ, Oehmichen M. Time of drug elimination in chronic drug abusers. Case study of 52 patients in a "low-step" detoxification ward. Forensic SciInt 2001; 119: 248-253.
66. Lowe RH, Abraham TT, Darwin WD, Herning R, Cadet JL, Huestis MA. Extended urinary Delta9-tetrahydrocannabinol excretion in chronic cannabis users precludes use as a biomarker of new drug exposure. Drug Alcohol Depend 2009; 105: 24-32.
67. Goulle JP, Saussereau E, Lacroix C. [Delta-9-tetrahydrocannabinol pharmacokinetics]. Ann Pharm Fr 2008; 66: 232-244.
68. Halldin MM, Andersson LK, Widman M, Hollister LE. Further urinary metabolites of delta 1-tetrahydrocannabinol in man.Arzneimittelforschung 1982; 32: 1135-1138.
69. Huestis MA, Cone EJ. Urinary excretion half-life of 11-nor-9-carboxy-delta9-tetrahydrocannabinol in humans.Ther Drug Monit 1998; 20: 570-576.
70. Kelly P, Jones RT. Metabolism of tetrahydrocannabinol in frequent and infrequent marijuana users. J Anal Toxicol 1992; 16: 228-235.
71. Johansson EK, Hollister LE, Halldin MM. Urinary elimination half-life of delta-1-tetrahydrocannabinol-7-oic acid in heavy marijuana users after smoking.NIDA Res Monogr 1989; 95: 457-458.
72. Manno JE, Manno BR, Kemp PM, Alford DD, Abukhalaf IK, McWilliams ME, et al. Temporal indication of marijuana use can be estimatedfrom plasma and urine concentrations of delta9-tetrahydrocannabinol, 11-hydroxy-delta9-tetrahydrocannabinol, and 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid. J Anal Toxicol 2001; 25: 538-549.
73. Altunkaya D, Clatworthy AJ, Smith RN, Start IJ. Urinary cannabinoid analysis: comparison of four immunoassays with gas chromatography-mass spectrometry. Forensic Sci Int 1991; 50: 15-22.
74. Fraser AD, Worth D. Monitoring urinary excretion of cannabinoids by fluorescence-polarization immunoassay: a cannabinoid-to-creatinine ratio study. Ther Drug Monit 2002; 24: 746-750.
75. Kerrigan S, Phillips Jr WH, Jr. Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine. Clin Chem 2001; 47: 540-547.
76. Fraser AD, Worth D. Urinary excretion profiles of 11-nor-9-carboxy-delta9-tetrahydrocannabinol and 11-hydroxy-delta9-THC: cannabinoid metabolites to creatinine ratio study IV. Forensic SciInt 2004; 143: 147-152.
77. Sharma P, Bharath MM and Murthy P. Qualitative high performance thin layer chromatography (HPTLC) analysis of cannabinoids in urine samples of Cannabis abusers. Indian J Med Res 2010; 132: 201-208.
78. Huestis MA, Mitchell JM and Cone EJ. Detection times of marijuana metabolites in urine by immunoassay and GC-MS. J Anal Toxicol 1995; 19: 443-449.
79. Hidvegi E, Somogyi GP. Detection of cannabigerol and its presumptive metabolite in human urine after Cannabis consumption.Pharmazie 2010; 65: 408-411.
80. Hollister LE. Interactions of cannabis with other drugs in man.NIDA Res Monogr 1986; 68: 110-116.
81. Ramsay M, Percy A.Drug misuse declared: results of the 1994 British Crime Survey. London:Home office; 1996.
82. Huestis MA.Human cannabinoid pharmacokinetics. ChemBiodivers 2007; 4: 1770-1804.
83. Kalant OJ. Report of the Indian Hemp Drugs Commission, 1893-94: a critical review. Int J Addict 1972; 7: 77-96.
84. Niedbala RS, Kardos KW, Fritch DF, Kunsman KP, Blum KA, Newland GA, et al. Passive cannabis smoke exposure and oral fluid testing. II. Two studies of extreme cannabis smoke exposure in a motor vehicle. J Anal Toxicol 2005; 29: 607-615.
85. Garry A, Rigourd V, Amirouche A, Fauroux V, Aubry S, Serreau R. Cannabis and breastfeeding. J Toxicol 2009; 2009: 1-5.
86. Perez-Reyes M, Wall ME. Presence of delta9-tetrahydrocannabinol in human milk. N Engl J Med 1982; 307: 819-820.
87. Fernandez-Ruiz J, Gomez M, Hernandez M, de Miguel R, Ramos JA. Cannabinoids and gene expression during brain development. Neurotox Res 2004; 6: 389-401.
88. Liston J. Breastfeeding and the use of recreational drugs--alcohol, caffeine, nicotine and marijuana. Breastfeed Rev 1998; 6: 27-30.