Natural cannabinoids of cannabis and methods of analysis

Cannabis sativa L. - Botany and Biotechnology

Volumn , Issue , 2017, Pages 161-182

  Radwan, Mohamed M ^a   Wanas, Amira S ^a   Chandra, Suman ^a   ElSohly, Mahmoud A ^a,b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85033607025     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-319-54564-6_7     Document Type: Chapter

References (51)

1. Ahmed SA, Ross SA, Slade D, Radwan MM, Zulfiqar F, ElSohly MA (2008) Cannabinoid ester constituents from high-potency Cannabis sativa. J Nat Prod 71(4):536-542
2. Ahmed SA, Ross SA, Slade D, Radwan MM, Khan IA, ElSohly MA (2015) Minor oxygenated cannabinoids from high potency Cannabis sativa L. Phytochemistry 117:194-199
3. Clarke R, Merlin M (2013) Cannabis: evolution and ethnobotany. Univ of California Press
4. De Backer B, Debrus B, Lebrun P, Theunis L, Dubois N, Decock L, Verstraete A, Hubert P, Charlier C (2009) Innovative development and validation of an HPLC/DAD method for the qualitative and quantitative determination of major cannabinoids in cannabis plant material. J Chromatogr B 877(32):4115-4124
5. de Oliveira GL, Voloch MH, Sztulman GB, Neto ON, Yonamine M (2008) Cannabinoid contents in cannabis products seized in São Paulo, Brazil, 2006-2007. Forensic Toxicol 26(1):31-35
6. de Ropp RS (1960) Chromatographic separation of the phenolic compounds of Cannabis sativa. J Am Pharm Assoc 49(12):756-758
7. Devinsky O, Cilio MR, Cross H, Fernandez-Ruiz J, French J, Hill C, Katz R, Di Marzo V, Jutras-Aswad D, Notcutt WG (2014) Cannabidiol: pharmacology and potential therapeutic role in epilepsy and other neuropsychiatric disorders. Epilepsia 55(6):791-802
8. Elsohly MA, Ross SA (2002) Method of preparing delta-9-tetrahydrocannabinol U.S. Patent,365,416
9. ElSohly MA, Slade D (2005) Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci 78(5):539-548
10. ElSohly MA, Mehmedic Z, Foster S, Gon C, Chandra S, Church JC (2016a) Changes in cannabis potency over the last 2 decades (1995-2014): analysis of current data in the United States. Biol Psychiatry 79(7):613-619
11. ElSohly MA, Radwan MM, Gul W, Chandra S, Galal A (2016) Phytochemistry of Cannabis sativa. In: A.D. Kinghorn, H. Falk and J. Kobayashi (ed) Progress in the chemistry of organic natural products. Springer International Publishing Switzerland 103:1-36
12. Fetterman PS, Keith ES, Waller CW, Guerrero O, Doorenbos NJ, Quimby MW (1971) Mississippi-grown Cannabis sativa L.: preliminary observation on chemical definition of phenotype and variations in tetrahydrocannabinol content versus age, sex, and plant part. J Pharm Sci 60(8):1246-1249
13. Fischedick JT, Glas R, Hazekamp A, Verpoorte R (2009) A qualitative and quantitative HPTLC densitometry method for the analysis of cannabinoids in Cannabis sativa L. Phytochem Anal 20(5):421-426
14. Florian-Ramirez NM, Garzon-Mendez WF, Parada-Alfonso F (2012) Gas chromatography in forensic chemistry: cannabinoids content in marijuana leaves (Cannabis sativa L.) from Colombia, In Tech
15. Gaoni Y, Mechoulam R (1964) Isolation, structure, and partial synthesis of an active constituent of hashish. J Am Chem Soc 86(8):1646-1647
16. Giese MW, Lewis MA, Giese L, Smith KM (2015) Method for the analysis of cannabinoids and terpenes in Cannabis. JAOAC International 98(6):1503-1522
17. Gill E (1971) Propyl homologue of tetrahydrocannabinol: its isolation from Cannabis, properties, and synthesis. J Chem Soc C, Organic, pp 579-582
18. Grotenhermen F, Müller-Vahl K (2012) The therapeutic potential of cannabis and cannabinoids. Dtsch Arztebl Int 109(29-30):495-501
19. Gul W, Gul SW, Radwan MM, Wanas AS, Khan II, Sharaf MH, ElSohly MA (2015) Determination of 11 cannabinoids in biomass and extracts of different varieties of Cannabis using high-performance liquid chromatography. JAOAC Int 98(6):1523-1528
20. Harvey DJ (1976) Characterization of the butyl homologs of A1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry. J Pharm Pharmacol 28:280-285
21. Hazekamp A, Peltenburg A, Verpoorte R, Giroud C (2005) Chromatographic and spectroscopic data of cannabinoids from Cannabis sativa L. J Liq Chromatogr Relat Technol 28(15):2361-2382
22. Heo S, Yoo GJ, Choi JY, Park HJ, Do J-A, Cho S, Baek SY, Park S-K (2016) Simultaneous analysis of cannabinoid and synthetic cannabinoids in dietary supplements using UPLC with UV and UPLC-MS-MS. J Anal Toxicol 40(5):350-359
23. Hillig KW (2005) Genetic evidence for speciation in Cannabis (Cannabaceae). Genet Resour Crop Evol 52(2):161-180
24. Joyce C, Curry S (1970) The botany and chemistry of cannabis. Churchill, London
25. Korte F, Sieper H, Tira S (1965) New results on hashish-specific constituents. Bull Narc 17(1):35-43
26. Mechoulam R and Gaoni Y (1967) Recent advances in the chemistry of hashish. Fortschritte der Chemie Organischer Naturstoffe/Progress in the chemistry of organic natural products/Progrès dans la Chimie des Substances Organiques Naturelles, Springer, pp 175-213
27. Mechoulam R, Ben-Zvi Z, Yagnitinsky B, Shani A (1969) A new tetrahydrocannabinolic acid. Tetrahedron Lett 10(28):2339-2341
28. 1-Tetrahydrocannabivarolic acid, new constituent of Cannabis sativa. C R Acad Sci Ser C 276:205-207
29. Pate DW (1999) The phytochemistry of Cannabis: its ecological and evolutionary implications. Advances in hemp research Haworth Press, NY, pp 21-42
30. Pellegrini M, Marchei E, Pacifici R, Pichini S (2005) A rapid and simple procedure for the determination of cannabinoids in hemp food products by gas chromatography-mass spectrometry. J Pharm Biomed Anal 36(5):939-946
31. Radwan MM, ElSohly MA, El-Alfy AT, Ahmed SA, Slade D, Husni AS, Manly SP, Wilson L, Seale S, Cutler SJ, Ross SA (2015) Isolation and pharmacological evaluation of minor cannabinoids from high-potency Cannabis sativa. J Nat Prod 78(6):1271-1276
32. 9-tetrahydrocannabinolic acid B. Acta Chem Scand B 29(3)
33. Ross S, ElSohly M (1995) Constituents of Cannabis Sativa L. XXVIII. A review of the natural constituents, 1980-1994. Zagazig J Pharm Sci 4:1-10
34. Shoyama Y, Hirano H, Makino H, Umekita N, Nishioka I (1977) Cannabis. X. The isolation and structures of four new propyl cannabinoid acids, tetrahydrocannabivarinic acid, cannabidi- varinic acid, cannabichromevarinic acid and cannabigerovarinic acid, from Thai Cannabis, 'Meao variant'. Chem Pharm Bull 25:2306-2311
35. Small E (2015) Evolution and classification of Cannabis sativa (marijuana, hemp) in relation to human utilization. Bot Rev 81(3):189-294
36. Small E, Beckstead H (1973) Cannabinoid phenotypes in Cannabis sativa
37. Small E, Marcus D (2002) Hemp: A new crop with new uses for North America. Trends in new crops and new uses, pp 284-326
38. Szabady B, Hidvegi E, Nyiredy S (2002) Determination of neutral cannabinoids in hemp samples by overpressured-layer chromatography. Chromatographia 56(1):S165-S168
39. Trofin IG, Dabija G, Vaireanu DI, Filipescu L (2012) Long-term storage and cannabis oil stability. Rev Chim 63(3):293-297
40. Turner CE, Hadley K, Fetterman PS (1973a) Constituents of Cannabis Sativa. VI. Propyl homologs in samples of known geographical origin. J Pharm Sci 62:1739-1741
41. Turner CE, Hadley KW, Fetterman PS, Doorenbos NJ, Quimby MW, Waller C (1973b) Constituents of Cannabis sativa L. IV: Stability of cannabinoids in stored plant material. J Pharm Sci 62(10):1601-1605
42. Turner CE, Elsohly MA, Boeren EG (1980) Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod 43(2):169-234
43. UNODC (2009) Recommended methods for the identification and analysis of cannabis and cannabis products. United Nations Office on Drugs and Crime, Vienna
44. Verwey A, Witte A (1972) A rapid method of preparation of 1-THC by isolation of 1-THC acid from hashish. Pharmaceutisch Weekblad 107(27):415
45. Wang M, Wang YH, Avula B, Radwan MM, Wanas AS, van Antwerp J, Parcher J, ElSohly MA, Khan IA (2016) Quantitative determination of cannabinoids in cannabis using ultra high performance supercritical fluid chromatography and diode array/mass spectrometric detection. J Forensic Sci doi:10.1111/1556-4029
46. Watanabe K (2005) Cannabinoids and their metabolites. Springer, Drugs and Poisons in Humans, pp 187-194
47. Wollner H, Matchett JR, Levine J, Loewe S (1942) Isolation of a physiologically active tetrahydrocannabinol from Cannabis sativa resin. J Am Chem Soc 64(1):26-29
48. Xiaoyan Wang DM, Searfoss Jody, Telepchak Michael (2016) Determination of cannabinoid content and pesticide rediues in Cannabis edible beverages. LCGC 34(10):20-27
49. Yamauchi T, Shoyama Y, Aramaki H, Azuma T, Nishioka I (1967) Tetrahydrocannabinolic acid, a genuine substance of tetrahydrocannabinol. Chem Pharm Bull 15:1075-1076
50. Yotoriyama M, Ishiharajima E, Kato Y, Nagato A, Sekita S, Watanabe K, Yamamoto I (2005) Identification and determination of cannabinoids in both commercially available and cannabis oils stored long term. J Health Sci 51(4):483-487
51. 9-THC dimer possessing a unique methylene bridge, isolated from Cannabis sativa. Tetrahedron Lett 53(28):3560-3562