European Journal of Chemistry

From ancient Asian relics to contemporaneity: A review of historical and chemical aspects of Cannabis

Article Sidebar

PDF
Published: Sep 30, 2023
DOI: https://doi.org/10.5155/eurjchem.14.3.393-400.2442
Keywords:
Cannabinoids, Phytochemistry, Pharmaceuticals, History of science, Structure elucidation, Traditional medicine
Section
Review Article
Issue
Vol. 14 No. 3 (2023): September 2023
Dates
Received 2023-04-17
Accepted 2023-06-04
Published 2023-09-30
Crossmark


Main Article Content

Gabriel Vitor de Lima Marques
Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Belo Horizonte, 31270-901, Brazil
https://orcid.org/0000-0002-7558-5555
Renata Barbosa de Oliveira
Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Belo Horizonte, 31270-901, Brazil
https://orcid.org/0000-0001-5884-2567

Abstract

From the Himalayan mountains to the South American coast, Cannabis, a general term for plants of the genus Cannabis, with thousands of years of contact with humankind, shows its versatility as food tools such as hemp, religious and hedonistic input, and other purposes through the millennia, according to the populations in question. In this paper, a review of the context of the use of Cannabis and its place in world history is presented, from ancient Mesopotamian relics, traditional Chinese and Ayurvedic medicines, to the reasoning behind the isolation and structural elucidation of three phytocannabinoids and the spread of Cannabis throughout the world.


icon graph This Abstract was viewed 2229 times | icon graph Article PDF downloaded 749 times

How to Cite
(1)
Marques, G. V. de L.; Oliveira, R. B. de. From Ancient Asian Relics to Contemporaneity: A Review of Historical and Chemical Aspects of Cannabis. Eur. J. Chem. 2023, 14, 393-400.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Ranalli, P. Advances in hemp research; CRC Press: London, England, 1999.
https://doi.org/10.1201/9781498705820

[2]. Moliterni, V. M. C.; Cattivelli, L.; Ranalli, P.; Mandolino, G. The sexual differentiation of Cannabis sativa L.: A morphological and molecular study. Euphytica 2004, 140, 95-106.
https://doi.org/10.1007/s10681-004-4758-7

[3]. Gupta, R. C. Nutraceuticals: Efficacy, safety and toxicity; Academic Press: San Diego, CA, 2016.

[4]. dos Santos, N. A.; Romão, W. Cannabis - A state of the art about the millenary plant: Part I. Forensic Chem. 2023, 32, 100470.
https://doi.org/10.1016/j.forc.2023.100470

[5]. Preedy, V. R. Handbook of Cannabis and Related Pathologies; Elsevier, 2017.

[6]. Raman, V.; Lata, H.; Chandra, S.; Khan, I. A.; ElSohly, M. A. Morpho-Anatomy of Marijuana (Cannabis sativa L.). In Cannabis sativa L. - Botany and Biotechnology; Springer International Publishing: Cham, 2017; pp. 123-136.
https://doi.org/10.1007/978-3-319-54564-6_5

[7]. Tauger, M. B. Agriculture in World History; Routledge, 2014.

[8]. Clarke, R. C.; Merlin, M. D. Cannabis: Evolution and Ethnobotany; University of California Press: Berkeley, CA, 2013.

[9]. Touw, M. The religious and medicinal uses ofcannabisin China, India and Tibet. J. Psychoactive Drugs 1981, 13, 23-34.
https://doi.org/10.1080/02791072.1981.10471447

[10]. Odani, S.; Odani, S. Isolation and primary structure of a methionine- and cystine-rich seed protein ofcannabis sativa. Biosci. Biotechnol. Biochem. 1998, 62, 650-654.
https://doi.org/10.1271/bbb.62.650

[11]. Carvalho, I. S.; Miranda, I.; Pereira, H. Evaluation of oil composition of some crops suitable for human nutrition. Ind. Crops Prod. 2006, 24, 75-78.
https://doi.org/10.1016/j.indcrop.2006.03.005

[12]. Wang, X.-S.; Tang, C.-H.; Yang, X.-Q.; Gao, W.-R. Characterization, amino acid composition and in vitro digestibility of hemp (Cannabis sativa L.) proteins. Food Chem. 2008, 107, 11-18.
https://doi.org/10.1016/j.foodchem.2007.06.064

[13]. Li, H.-L. An archaeological and historical account of cannabis in China. Econ. Bot. 1973, 28, 437-448.
https://doi.org/10.1007/BF02862859

[14]. Zuardi, A. W. History of cannabis as a medicine: a review. Rev. Bras. Psiquiatr. 2006, 28, 153-157.
https://doi.org/10.1590/S1516-44462006000200015

[15]. Zatta, A.; Monti, A.; Venturi, G. Eighty years of studies on industrial hemp in the Po valley (1930--2010). J. Nat. Fibers 2012, 9, 180-196.
https://doi.org/10.1080/15440478.2012.706439

[16]. Sainz Martinez, A.; Lanaridi, O.; Stagel, K.; Halbwirth, H.; Schnürch, M.; Bica-Schröder, K. Extraction techniques for bioactive compounds of cannabis. Nat. Prod. Rep. 2023, 40, 676-717.
https://doi.org/10.1039/D2NP00059H

[17]. Kalant, H. Medicinal use of cannabis: History and current status. Pain Res. Manag. 2001, 6, 80-91.
https://doi.org/10.1155/2001/469629

[18]. Russo, E. B. History of cannabis and its preparations in saga, science, and sobriquet. Chem. Biodivers. 2007, 4, 1614-1648.
https://doi.org/10.1002/cbdv.200790144

[19]. Merzouki, A.; Ed-derfoufi, F.; Molero Mesa, J. Hemp (Cannabis sativa L.) and abortion. J. Ethnopharmacol. 2000, 73, 501-503.
https://doi.org/10.1016/S0378-8741(00)00323-8

[20]. Lozano, I. The therapeutic use of cannabis sativa (L.) in Arabic medicine. J. Cannabis Therapeutics 2001, 1, 63-70.
https://doi.org/10.1300/J175v01n01_05

[21]. Russo, E. Cannabis in India: ancient lore and modern medicine. In Cannabinoids as Therapeutics; Birkhäuser-Verlag: Basel, 2005; pp. 1-22.
https://doi.org/10.1007/3-7643-7358-X_1

[22]. Warf, B. High points: An historical geography of cannabis. Geogr. Rev. 2014, 104, 414-438.
https://doi.org/10.1111/j.1931-0846.2014.12038.x

[23]. Carlini, E. A. A história da maconha no Brasil. J. Bras. Psiquiatr. 2006, 55, 314-317.
https://doi.org/10.1590/S0047-20852006000400008

[24]. Pisanti, S.; Bifulco, M. Medical Cannabis : A plurimillennial history of an evergreen. J. Cell. Physiol. 2019, 234, 8342-8351.
https://doi.org/10.1002/jcp.27725

[25]. Duvall, C. S. A brief agricultural history of cannabis in Africa, from prehistory to canna-colony. EchoGéo 2019, 48.
https://doi.org/10.4000/echogeo.17599

[26]. Abel, E. L. Marihuana: The first twelve thousand years; Springer: New York, NY, 2013.

[27]. Mathre, M. L. Cannabis in medical practice: A legal, historical and pharmacological overview of the therapeutic use of marijuana; Mathre, M. L., Ed.; McFarland: Jefferson, NC, 1997.

[28]. Crocq, M.-A. History of cannabis and the endocannabinoid system. Dialogues Clin. Neurosci. 2020, 22, 223-228.
https://doi.org/10.31887/DCNS.2020.22.3/mcrocq

[29]. Elsohly, M. A.; Turner, C. E.; Phoebe, C. H., Jr; Knapp, J. E.; Schiff, P. L., Jr; Slatkin, D. J. Anhydrocannabisativine, a New Alkaloid from Cannabis sativa L. J. Pharm. Sci. 1978, 67, 124.
https://doi.org/10.1002/jps.2600670135

[30]. Filer, C. N. Minnesota wild hemp: a crucial botanical source in early cannabinoid discovery. J. Cannabis Res. 2020, 2.
https://doi.org/10.1186/s42238-020-00031-3

[31]. Todd, A. R. Chemistry of the hemp drugs. Nature 1940, 146, 829-830.
https://doi.org/10.1038/146829a0

[32]. Mechoulam, R.; Hanuš, L. A historical overview of chemical research on cannabinoids. Chem. Phys. Lipids 2000, 108, 1-13.
https://doi.org/10.1016/S0009-3084(00)00184-5

[33]. Maioli, C.; Mattoteia, D.; Amin, H. I. M.; Minassi, A.; Caprioglio, D. Cannabinol: History, syntheses, and biological profile of the greatest "minor" cannabinoid. Plants 2022, 11, 2896.
https://doi.org/10.3390/plants11212896

[34]. Cahn, R. S. LXXXVI.-cannabis Indica resin. Part II. J. Chem. Soc. 1931, 630-638.
https://doi.org/10.1039/JR9310000630

[35]. Cahn, R. S. 174. Cannabis indica resin. Part III. The constitution of cannabinol. J. Chem. Soc. 1932, 1342.
https://doi.org/10.1039/jr9320001342

[36]. Pertwee, R. G. Cannabinoid pharmacology: the first 66 years: Cannabinoid pharmacology. Br. J. Pharmacol. 2006, 147, S163-S171.
https://doi.org/10.1038/sj.bjp.0706406

[37]. Adams, R.; Hunt, M.; Clark, J. H. Structure of cannabidiol, a product isolated from the marihuana extract of Minnesota wild hemp. I. J. Am. Chem. Soc. 1940, 62, 196-200.
https://doi.org/10.1021/ja01858a058

[38]. Adams, R.; Pease, D. C.; Clark, J. H.; Baker, B. R. Structure of Cannabinol. I. Preparation of an Isomer, 3-Hydroxy-1-n-amyl-6,6,9-trimethyl-6-dibenzopyran. J. Am. Chem. Soc. 1940, 62, 2197-2200.
https://doi.org/10.1021/ja01865a081

[39]. Adams, R.; Loewe, S.; Pease, D. C.; Cain, C. K.; Wearn, R. B.; Baker, R. B.; Wolff, H. Structure of cannabidiol. Viii. Position of the double bonds in cannabidiol. Marihuana activity of tetrahydrocannabinols. J. Am. Chem. Soc. 1940, 62, 2566-2567.
https://doi.org/10.1021/ja01866a510

[40]. Adams, R.; Cain, C. K.; Baker, B. R. Structure of Cannabinol. II. Synthesis of Two New Isomers, 3-Hydroxy-4-n-amyl- and 3-Hydroxy-2-n-amyl 6,6,9-Trimethyl-6-dibenzopyrans1. J. Am. Chem. Soc. 1940, 62, 2201-2204.
https://doi.org/10.1021/ja01865a082

[41]. Ghosh, R.; Todd, A. R.; Wright, D. C. 31. Cannabis indica. Part VI. The condensation of pulegone with alkyl resorcinols. A new synthesis of cannabinol and of a product with hashish activity. J. Chem. Soc. 1941, 137-140.
https://doi.org/10.1039/jr9410000137

[42]. Adams, R.; Pease, D. C.; Cain, C. K.; Baker, B. R.; Clark, J. H.; Wolff, H.; Wearn, R. B. Conversion of cannabidiol to a product with marihuana activity. A type reaction for synthesis of analogous substances. Conversion of cannabidiol to cannabinol. J. Am. Chem. Soc. 1940, 62, 2245-2246.
https://doi.org/10.1021/ja01865a508

[43]. Wollner, H. J.; Matchett, J. R.; Levine, J.; Loewe, S. Isolation of a physiologically active tetrahydrocannabinol from cannabis Sativa resin. J. Am. Chem. Soc. 1942, 64, 26-29.
https://doi.org/10.1021/ja01253a008

[44]. Hussain, T.; Jeena, G.; Pitakbut, T.; Vasilev, N.; Kayser, O. Cannabis sativa research trends, challenges, and new-age perspectives. iScience 2021, 24, 103391.
https://doi.org/10.1016/j.isci.2021.103391

[45]. Mechoulam, R.; Shvo, Y. Hashish-I. Tetrahedron 1963, 19, 2073-2078.
https://doi.org/10.1016/0040-4020(63)85022-X

[46]. Gaoni, Y.; Mechoulam, R. Isolation and structure of .DELTA.+- tetrahydrocannabinol and other neutral cannabinoids from hashish. J. Am. Chem. Soc. 1971, 93, 217-224.
https://doi.org/10.1021/ja00730a036

[47]. Hanuš, L. O.; Meyer, S. M.; Muñoz, E.; Taglialatela-Scafati, O.; Appendino, G. Phytocannabinoids: a unified critical inventory. Nat. Prod. Rep. 2016, 33, 1357-1392.
https://doi.org/10.1039/C6NP00074F

[48]. Mechoulam, R.; Hanuš, L. Cannabidiol: an overview of some chemical and pharmacological aspects. Part I: chemical aspects. Chem. Phys. Lipids 2002, 121, 35-43.
https://doi.org/10.1016/S0009-3084(02)00144-5

[49]. Mechoulam, R.; Gaoni, Y. The absolute configuration of δ1-tetrahydrocannabinol, the major active constituent of hashish. Tetrahedron Lett. 1967, 8, 1109-1111.
https://doi.org/10.1016/S0040-4039(00)90646-4

[50]. Jones, P. G.; Falvello, L.; Kennard, O.; Sheldrick, G. M.; Mechoulam, R. Cannabidiol. Acta Crystallogr. B 1977, 33, 3211-3214.
https://doi.org/10.1107/S0567740877010577

[51]. Brenneisen, R. Chemistry and analysis of phytocannabinoids and other cannabis constituents. In Forensic Science And Medicine; Humana Press: Totowa, NJ, 2007; pp. 17-49.
https://doi.org/10.1007/978-1-59259-947-9_2

[52]. Lu, D.; Potter, D. E. Cannabinoids and the cannabinoid receptors: An overview. In Handbook of Cannabis and Related Pathologies; Elsevier, 2017; pp. 553-563.
https://doi.org/10.1016/B978-0-12-800756-3.00068-5

[53]. Lal, S.; Shekher, A.; Puneet; Narula, A. S.; Abrahamse, H.; Gupta, S. C. Cannabis and its constituents for cancer: History, biogenesis, chemistry and pharmacological activities. Pharmacol. Res. 2021, 163, 105302.
https://doi.org/10.1016/j.phrs.2020.105302

[54]. Adams, R.; Pease, D. C.; Cain, C. K.; Clark, J. H. Structure of cannabidiol. VI. Isomerization of cannabidiol to tetrahydrocannabinol, a physiologically active product. Conversion of cannabidiol to cannabinol. J. Am. Chem. Soc. 1940, 62, 2402-2405.
https://doi.org/10.1021/ja01866a040

[55]. Douse, M. Contemporary music, drug attitudes and drug behaviour. Aust. J. Soc. Issues 1973, 8, 74-80.
https://doi.org/10.1002/j.1839-4655.1973.tb00507.x

[56]. Savishinsky, N. J. Rastafari in the Promised Land: The spread of a Jamaican socioreligious movement among the youth of west Africa. Afr. Stud. Rev. 1994, 37, 19.
https://doi.org/10.2307/524901

[57]. Singer, M.; Mirhej, G. High notes: The role of drugs in the making of jazz. J. Ethn. Subst. Abuse 2006, 5, 1-38.
https://doi.org/10.1300/J233v05n04_01

[58]. Sandberg, S. Cannabis culture: A stable subculture in a changing world. Criminol. Crim. Justice 2013, 13, 63-79.
https://doi.org/10.1177/1748895812445620

[59]. Kaminski, L. F. O movimento hippie nasceu em Moscou: imaginário anticomunista, contracultura e repressão no Brasil dos anos 1970. Antíteses 2017, 9, 437.
https://doi.org/10.5433/1984-3356.2016v9n18p437

[60]. Wünsch, S. How the Summer of Love came to San Francisco 50 years ago. https://www.dw.com/en/how-the-summer-of-love-came-to-san-francisco-50-years-ago/a-40236165 (accessed May 24, 2023).

[61]. Rehm, J.; Fischer, B. Cannabis legalization with strict regulation, the overall superior policy option for public health. Clin. Pharmacol. Ther. 2015, 97, 541-544.
https://doi.org/10.1002/cpt.93

[62]. Fischer, B.; Malta, M.; Messas, G.; Ribeiro, M. Introducing the evidence-based population health tool of the Lower-Risk Cannabis Use Guidelines to Brazil. Rev. Bras. Psiquiatr. 2019, 41, 550-555.
https://doi.org/10.1590/1516-4446-2018-0239

[63]. Anvisa autoriza primeiro produto à base de Cannabis. https://www.gov.br/anvisa/pt-br/assuntos/noticias-anvisa/2020/anvisa-autoriza-primeiro-produto-a-base-de-cannabis (accessed May 24, 2023).

[64]. Zellers, S. M.; Ross, J. M.; Saunders, G. R. B.; Ellingson, J. M.; Anderson, J. E.; Corley, R. P.; Iacono, W.; Hewitt, J. K.; Hopfer, C. J.; McGue, M. K.; Vrieze, S. Impacts of recreational cannabis legalization on cannabis use: a longitudinal discordant twin study. Addiction 2023, 118, 110-118.
https://doi.org/10.1111/add.16016

Supporting Agencies

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).