{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,4]],"date-time":"2026-06-04T23:41:38Z","timestamp":1780616498583,"version":"3.54.1"},"reference-count":27,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2025,8,22]],"date-time":"2025-08-22T00:00:00Z","timestamp":1755820800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Japan Science and Technology Agency.","award":["JPMJTR224B"],"award-info":[{"award-number":["JPMJTR224B"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Although cannabis is used in a wide range of fields, including medicine and pharmacology, its use is prohibited in Japan because it contains \u03949-tetrahydrocannabinol (\u03949-THC), a compound that exhibits narcotic effects. While cannabis is primarily detected via color-based screening methods at crime scenes, the reaction products and mechanisms associated with these screening methods have not been fully elucidated. To address this issue, the colored products were isolated via the diazo-coupling reactions of the major cannabinoids (cannabidiol, cannabinol, and \u03949-THC) in cannabis with the Fast Blue RR diazonium salt, and their structures were determined using NMR spectroscopy. As expected, azo compound 2 was formed from cannabidiol, whereas cannabinol and \u03949-THC produced quinoneimines 3 and 4, respectively. This study is expected to lead to the future development of more sensitive color-based reagents that produce fewer false positives.<\/jats:p>","DOI":"10.3390\/molecules30173462","type":"journal-article","created":{"date-parts":[[2025,8,22]],"date-time":"2025-08-22T13:47:49Z","timestamp":1755870469000},"page":"3462","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Isolating and Determining the Structures of Colored Products from the Reactions of Cannabinoids with Fast Blue RR"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4577-060X","authenticated-orcid":false,"given":"Kayo","family":"Nakamura","sequence":"first","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hikari","family":"Nishiguchi","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryosuke","family":"Arai","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Riho","family":"Hamajima","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroko","family":"Abe","sequence":"additional","affiliation":[{"name":"BioDesign Inc., IB Daiichi-Bld 6th Floor, 3-25-15 Nishi-Ikebukuro, Toshima-ku, Tokyo 171-0021, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4100-9426","authenticated-orcid":false,"given":"Akihiko","family":"Ishida","sequence":"additional","affiliation":[{"name":"Faculty of Engineering, Hokkaido University, Kita 13, Nishi 8, Kita-ku, Sapporo 060-8628, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4412-2144","authenticated-orcid":false,"given":"Manabu","family":"Tokeshi","sequence":"additional","affiliation":[{"name":"Faculty of Engineering, Hokkaido University, Kita 13, Nishi 8, Kita-ku, Sapporo 060-8628, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2622-4825","authenticated-orcid":false,"given":"Kyohei","family":"Higashi","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akiyoshi","family":"Saitoh","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5965-3987","authenticated-orcid":false,"given":"Hideyo","family":"Takahashi","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,8,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1002\/med.20135","article-title":"Pharmacological and therapeutic secrets of plant and brain (endo)cannabinoids","volume":"29","author":"Hanus","year":"2009","journal-title":"Med. Res. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"398","DOI":"10.1002\/jssc.201701003","article-title":"A review of methods for the chemical characterization of cannabis natural products","volume":"41","author":"Leghissa","year":"2018","journal-title":"J. Sep. Sci."},{"key":"ref_3","unstructured":"Ministry of Health, Labour and Welfare (2025, August 09). Available online: https:\/\/www.mhlw.go.jp\/content\/11120000\/001313370.pdf."},{"key":"ref_4","unstructured":"Ministry of Health, Labour and Welfare (2025, August 15). Available online: https:\/\/www.mhlw.go.jp\/content\/11126000\/001279247.pdf."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1186\/s42238-021-00062-4","article-title":"The biosynthesis of the cannabinoids","volume":"3","author":"Tahir","year":"2021","journal-title":"J. Cannabis Res."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"e94","DOI":"10.1038\/tp.2012.15","article-title":"Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia","volume":"2","author":"Leweke","year":"2012","journal-title":"Transl. Psychiatry"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/j.seizure.2016.01.004","article-title":"CBD-enriched medical cannabis for intractable pediatric epilepsy. The current Israeli experience","volume":"35","author":"Tzadok","year":"2016","journal-title":"Seizure"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"108205","DOI":"10.1016\/j.yebeh.2021.108205","article-title":"Cross-sectional and longitudinal evaluation of cannabidiol (CBD) product use and health among people with epilepsy","volume":"122","author":"Strickland","year":"2021","journal-title":"Epilepsy Behav."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"118359","DOI":"10.1016\/j.indcrop.2024.118359","article-title":"Health benefits, pharmacological properties, and metabolism of cannabinol: A comprehensive review","volume":"213","author":"Khouchlaa","year":"2024","journal-title":"Ind. Crops Prod."},{"key":"ref_10","first-page":"27","article-title":"A Study on the Culture and Sciences of the Cannabis and Marihuana XXIV","volume":"37","author":"Watanabe","year":"2013","journal-title":"Bull. Hokuriku Univ."},{"key":"ref_11","unstructured":"Balfour, A. (1911). Fourth Report of the Wellcome Tropical Research Laboratories at the Gordon Memorial College, Khartoum, Bailli\u00e8re, Tindall & Cox."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"196","DOI":"10.1021\/ja01858a058","article-title":"Structure of cannabidiol, a product isolated from the marihuana extract of Minnesota wild hemp. I","volume":"62","author":"Adams","year":"1940","journal-title":"J. Am. Chem. Soc."},{"key":"ref_13","first-page":"175","article-title":"Recent advances in the chemistry of hashish","volume":"25","author":"Mechoulam","year":"1967","journal-title":"Fortschr. Chem. Org. Naturst."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"5615","DOI":"10.1016\/0040-4020(68)88159-1","article-title":"Hashish\u2013XIII: On the nature of the beam test","volume":"24","author":"Mechoulam","year":"1968","journal-title":"Tetrahedron"},{"key":"ref_15","first-page":"193","article-title":"The detection of Cannabis indica. A new test","volume":"20","author":"Ghamrawy","year":"1937","journal-title":"J. Egypt. Med. Assoc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"724","DOI":"10.1002\/ardp.19843170814","article-title":"Zur Kenntnis der Ghamrawy-Reaktion auf Haschisch und Marihuana","volume":"317","author":"Kovar","year":"1984","journal-title":"Arch. Pharm."},{"key":"ref_17","first-page":"224","article-title":"Identification and assay of Cannabis indica","volume":"21","author":"Duquenois","year":"1938","journal-title":"J. Egypt. Med. Assoc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1002\/ardp.19883210502","article-title":"The Duquenois reaction for hashish and marihuana","volume":"321","author":"Kovar","year":"1988","journal-title":"Arch. Pharm."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1016\/S0021-9673(01)95077-0","article-title":"Zur chemischen Klassifizierung von Pflanzen XXIV. Untersuchung von Haschisch-Inhaltsstoffen durch D\u00fcnnschichtchromatographie","volume":"13","author":"Korte","year":"1964","journal-title":"J. Chromatogr."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"100212","DOI":"10.1016\/j.forc.2019.100212","article-title":"Experimental and ab initio investigation of the products of reaction from \u03949-tetrahydrocannabinol (\u03949-THC) and the fast blue BB spot reagent in presumptive drug tests for cannabinoids","volume":"17","author":"Acosta","year":"2020","journal-title":"Forensic Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"854","DOI":"10.1111\/1556-4029.14659","article-title":"Color determination method and evaluation of methods for the detection of cannabinoids by thin-layer chromatography (TLC)","volume":"66","author":"Maia","year":"2021","journal-title":"J. Forensic Sci."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"411","DOI":"10.1248\/yakushi.22-00198","article-title":"Determination of 11 Cannabinoids in Cannabis sativa L. by Liquid Chromatography Quadrupole Time-of-Flight Mass Spectrometry (LC-Q-TOF-MS)","volume":"143","author":"Tanaka","year":"2023","journal-title":"Yakugaku Zasshi"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1016\/j.lfs.2005.09.011","article-title":"Chemical constituents of marijuana: The complex mixture of natural cannabinoids","volume":"78","author":"ElSohly","year":"2005","journal-title":"Life Sci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"13506","DOI":"10.1021\/jp0755645","article-title":"Effect of cooperative hydrogen bonding in azo\u2013hydrazone tautomerism of azo dyes","volume":"111","author":"Doruker","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1111\/j.1478-4408.2005.tb00266.x","article-title":"Visible absorption spectra of some novel heteroarylazo disperse dyes derived from 2-hydroxy-1,4-nephthoquinone","volume":"121","author":"Karci","year":"2005","journal-title":"Color. Technol."},{"key":"ref_26","unstructured":"Webster, G.R.B., Sarna, L.P., and Mechoulam, R. (2008). Conversion of CBD to \u03948-THC and \u03949-THC. (7399872B2), U.S. Patent."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1002\/pca.787","article-title":"NMR assignments of the major cannabinoids and cannabiflavonoids isolated flowers of Cannabis sativa","volume":"15","author":"Choi","year":"2004","journal-title":"Phytochem. Anal."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/17\/3462\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T18:34:06Z","timestamp":1760034846000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/17\/3462"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,8,22]]},"references-count":27,"journal-issue":{"issue":"17","published-online":{"date-parts":[[2025,9]]}},"alternative-id":["molecules30173462"],"URL":"https:\/\/doi.org\/10.3390\/molecules30173462","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,8,22]]}}}