ACS Publications. Most Trusted. Most Cited. Most Read
(−)-trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Nat. Prod. 2021, 84, 2, 531-536
    Note

    (−)-trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (1)

    Journal of Natural Products

    Cite this: J. Nat. Prod. 2021, 84, 2, 531–536
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.0c01034
    Published February 10, 2021
    Copyright © 2021 American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The (−)-trans-Δ9-tetrahydrocannabiphorol (Δ9-THCP, 1) content of the inflorescence from six Cannabis sativa chemotypes, including 14 plants of distinct genotypes, and two extracts was determined quantitatively via high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). This represents the first comprehensive quantitative screening for 1 from various C. sativa chemotypes. Compound 1 was detected in all 13 inflorescence samples originating from “(−)-trans-Δ9-tetrahydrocannabinol (Δ9-THC, 2) dominant” C. sativa chemotypes, but was not detected in a “cannabidiol (CBD, 3) dominant” chemotype. The inflorescence content of 1 ranged approximately from 0.0023% to 0.0136% (w/w). Comprehensive inflorescence sampling was performed for each specimen investigated. A trend between inflorescence cannabinoid potency and the location of which the inflorescence was sampled on the C. sativa plant was observed for the three cannabinoids tested (1–3). The preliminary results obtained indicate Δ9-THCP (1) may have a higher degree of prevalence in C. sativa inflorescence than previously estimated.

    Copyright © 2021 American Chemical Society and American Society of Pharmacognosy

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jnatprod.0c01034.

    • Additional information (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 22 publications.

    1. Willi Schirmer, Ilche Gjuroski, Martina Vermathen, Julien Furrer, Stefan Schürch, Wolfgang Weinmann. Isolation and characterization of synthesis intermediates and side products in hexahydrocannabiphorol. Drug Testing and Analysis 2025, 17 (4) , 531-543. https://doi.org/10.1002/dta.3759
    2. Marica Hundertmark, Laura Besch, Jörg Röhrich, Tanja Germerott, Cora Wunder. Characterising a New Cannabis Trend: Extensive Analysis of Semi‐Synthetic Cannabinoid‐Containing Seizures From Germany. Drug Testing and Analysis 2025, 22 https://doi.org/10.1002/dta.3886
    3. Ysé Jagailloux, Fabienne Le Saos, Amélie Rouille, Jean Luc Carre. Consommation de Delta-9-tetrahydrocannabiphorol (THCP) en « space cake » : à propos d’un cas. Toxicologie Analytique et Clinique 2025, 37 (1) , 77-81. https://doi.org/10.1016/j.toxac.2024.07.004
    4. Daniel Greer, Jennifer Atherton, Justina Girgis. Psychosis and suicide attempt following a single use of delta‐9‐tetrahydrocannabiphorol: A case report. Psychiatry and Clinical Neurosciences Reports 2025, 4 (1) https://doi.org/10.1002/pcn5.70060
    5. Céline Duchateau, Caroline Stévigny, Jehan Waeytens, Eric Deconinck. Chromatographic and Spectroscopic Analyses of Cannabinoids: A Narrative Review Focused on Cannabis Herbs and Oily Products. Molecules 2025, 30 (3) , 490. https://doi.org/10.3390/molecules30030490
    6. Stephen Goldman. Measurement uncertainty revealed: The impacts of Certified Reference Material (CRM) on cannabinoid concentrations in the cannabis testing industry. Talanta Open 2024, 10 , 100344. https://doi.org/10.1016/j.talo.2024.100344
    7. Cristian Caprari, Elena Ferri, Maria Angela Vandelli, Cinzia Citti, Giuseppe Cannazza. An emerging trend in Novel Psychoactive Substances (NPSs): designer THC. Journal of Cannabis Research 2024, 6 (1) https://doi.org/10.1186/s42238-024-00226-y
    8. Giovanni A. Ramirez, Maite L. Docampo-Palacios, Tesfay T. Tesfatsion, Monica K. Pittiglio, Kyle P. Ray, Westley Cruces. The Impact of Hemp Derived Cannabinoid Potency from Consumer Product Goods on in vitro Lung and Liver Cells. Natural Product Communications 2024, 19 (11) https://doi.org/10.1177/1934578X241299497
    9. Liesl K. Janssens, Katleen Van Uytfanghe, Jeffrey B. Williams, Kirk W. Hering, Donna M. Iula, Christophe P. Stove. Investigation of the intrinsic cannabinoid activity of hemp-derived and semisynthetic cannabinoids with β-arrestin2 recruitment assays—and how this matters for the harm potential of seized drugs. Archives of Toxicology 2024, 98 (8) , 2619-2630. https://doi.org/10.1007/s00204-024-03769-4
    10. Subhadip Banerjee, Debolina Saha, Rohit Sharma, Wuttichai Jaidee, Panupong Puttarak, Nathorn Chaiyakunapruk, Rawiwan Chaoroensup. Phytocannabinoids in neuromodulation: From omics to epigenetics. Journal of Ethnopharmacology 2024, 330 , 118201. https://doi.org/10.1016/j.jep.2024.118201
    11. Lutfun Nahar, Phanuphong Chaiwut, Sarita Sangthong, Tinnakorn Theansungnoen, Satyajit D. Sarker. Progress in the analysis of phytocannabinoids by HPLC and UPLC (or UHPLC) during 2020–2023. Phytochemical Analysis 2024, 35 (5) , 927-989. https://doi.org/10.1002/pca.3374
    12. Mehdi Haghdoost, Scott Young, Alisha K. Holloway, Matthew Roberts, Ivori Zvorsky, Marcel O. Bonn-Miller. CBD Versus CBDP: Comparing In Vitro Receptor-Binding Activities. International Journal of Molecular Sciences 2024, 25 (14) , 7724. https://doi.org/10.3390/ijms25147724
    13. Rie Tanaka, Ruri Kikura-Hanajiri. Identification of hexahydrocannabinol (HHC), dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC) and hexahydrocannabiphorol (HHCP) in electronic cigarette cartridge products. Forensic Toxicology 2024, 42 (1) , 71-81. https://doi.org/10.1007/s11419-023-00667-9
    14. Yufei Cheng, Kang Ning, Yongzhong Chen, Cong Hou, Haibin Yu, Huatao Yu, Shilin Chen, Xiaotong Guo, Linlin Dong. Identification of histone acetyltransferase genes responsible for cannabinoid synthesis in hemp. Chinese Medicine 2023, 18 (1) https://doi.org/10.1186/s13020-023-00720-0
    15. Justin Bueno, Solmaz Alborzi, Eric A. Greenbaum. Vapor Phase Terpenes Mitigate Oxidative Degradation of Cannabis sativa Inflorescence Cannabinoid Content in an Accelerated Stability Study. Cannabis and Cannabinoid Research 2023, 8 (5) , 887-898. https://doi.org/10.1089/can.2021.0207
    16. Abbey C.E. Rokeby, Bryony V. Natale, David R.C. Natale. Cannabinoids and the placenta: Receptors, signaling and outcomes. Placenta 2023, 135 , 51-61. https://doi.org/10.1016/j.placenta.2023.03.002
    17. Damian Robert Hall, Justin S Sinclair, Deep Jyoti Bhuyan, Cheang Khoo, Chun Guang Li, Jerome Sarris, Mitchell Low. Quality control of cannabis inflorescence and oil products: Response factors for the cost-efficient determination of ten cannabinoids by HPLC. Talanta Open 2022, 5 , 100112. https://doi.org/10.1016/j.talo.2022.100112
    18. Manuela Carla Monti, Priska Frei, Sophie Weber, Eva Scheurer, Katja Mercer-Chalmers-Bender. Beyond Δ9-tetrahydrocannabinol and cannabidiol: chemical differentiation of cannabis varieties applying targeted and untargeted analysis. Analytical and Bioanalytical Chemistry 2022, 414 (13) , 3847-3862. https://doi.org/10.1007/s00216-022-04026-2
    19. Yi Liu, Hong-Yan Liu, Sheng-Hong Li, Wei Ma, Ding-Tao Wu, Hua-Bin Li, Ai-Ping Xiao, Liang-Liang Liu, Fan Zhu, Ren-You Gan. Cannabis sativa bioactive compounds and their extraction, separation, purification, and identification technologies: An updated review. TrAC Trends in Analytical Chemistry 2022, 149 , 116554. https://doi.org/10.1016/j.trac.2022.116554
    20. Simon Vlad Luca, Lukas Braumann, Melanie Gerigk, Oliver Frank, Mirjana Minceva. Separation of minor cannabinoids from hemp extract with trapping multiple dual mode liquid-liquid chromatography. Journal of Chromatography A 2021, 1658 , 462608. https://doi.org/10.1016/j.chroma.2021.462608
    21. Anna Laura Capriotti, Giuseppe Cannazza, Martina Catani, Chiara Cavaliere, Alberto Cavazzini, Andrea Cerrato, Cinzia Citti, Simona Felletti, Carmela Maria Montone, Susy Piovesana, Aldo Laganà. Recent applications of mass spectrometry for the characterization of cannabis and hemp phytocannabinoids: From targeted to untargeted analysis. Journal of Chromatography A 2021, 1655 , 462492. https://doi.org/10.1016/j.chroma.2021.462492
    22. Manica Balant, Airy Gras, Mario Ruz, Joan Vallès, Daniel Vitales, Teresa Garnatje. Traditional uses of Cannabis: An analysis of the CANNUSE database. Journal of Ethnopharmacology 2021, 279 , 114362. https://doi.org/10.1016/j.jep.2021.114362
    Download PDF
    Go to Journal of Natural Products
    Get e-Alerts
    Get e-Alerts

    Journal of Natural Products

    Cite this: J. Nat. Prod. 2021, 84, 2, 531–536
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.0c01034
    Published February 10, 2021
    Copyright © 2021 American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

    Article Views

    1250

    Altmetric

    -

    Citations

    22
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.