Literature DB >> 33614950

Origin of Δ9-Tetrahydrocannabinol Impurity in Synthetic Cannabidiol.

Cinzia Citti1,2,3, Fabiana Russo3, Pasquale Linciano3, Sarah Sylvana Strallhofer4, Francesco Tolomeo1, Flavio Forni3, Maria Angela Vandelli3, Giuseppe Gigli2, Giuseppe Cannazza2,3.   

Abstract

Introduction: Cannabidiol (CBD), the nonintoxicating constituent of cannabis, is largely employed for pharmaceutical and cosmetic purposes. CBD can be extracted from the plant or chemically synthesized. Impurities of psychotropic cannabinoids Δ9-tetrahydrocannabinol (Δ9-THC) and Δ8-THC have been found in extracted CBD, thus hypothesizing a possible contamination from the plant. Materials and
Methods: In this study, synthetic and extracted CBD samples were analyzed by ultrahigh-performance liquid chromatography coupled to high-resolution mass spectrometry and the parameters that can be responsible of the conversion of CBD into THC were evaluated by an accelerated stability test.
Results: In synthetic and extracted CBD no trace of THC species was detected. In contrast, CBD samples stored in the dark at room temperature on the benchtop for 3 months showed the presence of such impurities. Experiments carried out under inert atmosphere in the absence of humidity or carbon dioxide led to no trace of THC over time even at high temperature. Conclusions: The results suggested that the copresence of carbon dioxide and water from the air could be the key for creating the acidic environment responsible for the cyclization of CBD. These findings suggest that it might be appropriate to review the storage conditions indicated on the label of commercially available CBD. Copyright 2021, Mary Ann Liebert, Inc., publishers.

Entities:  

Keywords:  cannabidiol; impurity; liquid chromatography–mass spectrometry; Δ9-tetrahydrocannabinol

Mesh:

Substances:

Year:  2021        PMID: 33614950      PMCID: PMC7891213          DOI: 10.1089/can.2020.0021

Source DB:  PubMed          Journal:  Cannabis Cannabinoid Res        ISSN: 2378-8763


  22 in total

1.  Parental reporting of response to oral cannabis extracts for treatment of refractory epilepsy.

Authors:  Craig A Press; Kelly G Knupp; Kevin E Chapman
Journal:  Epilepsy Behav       Date:  2015-04-03       Impact factor: 2.937

2.  Distribution of tetrahydrocannabinolic acid in fresh wild cannabis.

Authors:  M Kimura; K Okamoto
Journal:  Experientia       Date:  1970-08-15

3.  [Synthesis and optical rotation of the (-)-cannabidiols].

Authors:  T Petrzilka; W Haefliger; C Sikemeier; G Ohloff; A Eschenmoser
Journal:  Helv Chim Acta       Date:  1967-03-10       Impact factor: 2.164

Review 4.  Synthetic Strategies for (-)-Cannabidiol and Its Structural Analogs.

Authors:  Byunghyuck Jung; Jungkyu K Lee; Jungnam Kim; Eunhye K Kang; Sang Yeong Han; Hee-Yoon Lee; Insung S Choi
Journal:  Chem Asian J       Date:  2019-10-08

Review 5.  Is cannabidiol a scheduled controlled substance? Origin makes the difference.

Authors:  Cinzia Citti; Pasquale Linciano; Giuseppe Cannazza
Journal:  Drug Discov Today       Date:  2020-02-13       Impact factor: 7.851

6.  Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability.

Authors:  William A Kinney; Mark E McDonnell; Hua Marlon Zhong; Chaomin Liu; Lanyi Yang; Wei Ling; Tao Qian; Yu Chen; Zhijie Cai; Dean Petkanas; Douglas E Brenneman
Journal:  ACS Med Chem Lett       Date:  2016-02-10       Impact factor: 4.345

7.  Cannabinoid Profiling of Hemp Seed Oil by Liquid Chromatography Coupled to High-Resolution Mass Spectrometry.

Authors:  Cinzia Citti; Pasquale Linciano; Sara Panseri; Francesca Vezzalini; Flavio Forni; Maria Angela Vandelli; Giuseppe Cannazza
Journal:  Front Plant Sci       Date:  2019-02-13       Impact factor: 5.753

8.  Phytochemical and Ecological Analysis of Two Varieties of Hemp (Cannabis sativa L.) Grown in a Mountain Environment of Italian Alps.

Authors:  Radmila Pavlovic; Sara Panseri; Luca Giupponi; Valeria Leoni; Cinzia Citti; Chiara Cattaneo; Maria Cavaletto; Annamaria Giorgi
Journal:  Front Plant Sci       Date:  2019-10-15       Impact factor: 5.753

9.  A Conversion of Oral Cannabidiol to Delta9-Tetrahydrocannabinol Seems Not to Occur in Humans.

Authors:  Gerhard Nahler; Franjo Grotenhermen; Antonio Waldo Zuardi; José A S Crippa
Journal:  Cannabis Cannabinoid Res       Date:  2017-05-01

10.  A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol.

Authors:  Cinzia Citti; Pasquale Linciano; Fabiana Russo; Livio Luongo; Monica Iannotta; Sabatino Maione; Aldo Laganà; Anna Laura Capriotti; Flavio Forni; Maria Angela Vandelli; Giuseppe Gigli; Giuseppe Cannazza
Journal:  Sci Rep       Date:  2019-12-30       Impact factor: 4.379

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  3 in total

1.  Selective Preparation and High Dynamic-Range Analysis of Cannabinoids in "CBD Oil" and Other Cannabis sativa Preparations.

Authors:  Takashi Ohtsuki; J Brent Friesen; Shao-Nong Chen; James B McAlpine; Guido F Pauli
Journal:  J Nat Prod       Date:  2022-01-06       Impact factor: 4.050

2.  Comparison of the in vitro Anti-Inflammatory Effect of Cannabidiol to Dexamethasone.

Authors:  Yiming Wang; Xue Wang; Yang Yang; Qianghua Quan; Tong Huo; Simin Yang; Ruijun Ju; Quan An
Journal:  Clin Cosmet Investig Dermatol       Date:  2022-09-16

3.  Cannabidiol-Loaded Mixed Polymeric Micelles of Chitosan/Poly(Vinyl Alcohol) and Poly(Methyl Methacrylate) for Trans-Corneal Delivery.

Authors:  Alejandro Sosnik; Ronya Ben Shabo; Hen Moshe Halamish
Journal:  Pharmaceutics       Date:  2021-12-13       Impact factor: 6.321

  3 in total

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