{"title":"鉴定电子香烟盒产品中的六氢大麻酚（HHC）、二氢-异四氢大麻酚（二氢-异-THC）和六氢大麻酚（HHCP）。","authors":"Rie Tanaka, Ruri Kikura-Hanajiri","doi":"10.1007/s11419-023-00667-9","DOIUrl":null,"url":null,"abstract":"<p><strong>Purpose: </strong>Since 2021, products claiming to contain hexahydrocannabinol (HHC) and hexahydrocannabiphorol (HHCP), which are tetrahydrocannabinol (THC) analogs, have been distributed via the Internet. Owing to the presence of three asymmetric carbons in their structure, HHC and HHCP have multiple stereoisomers. This study aimed to identify the actual stereoisomers of HHC and HHCP isolated from electronic cigarette cartridge products using nuclear magnetic resonance (NMR) spectroscopy.</p><p><strong>Methods: </strong>Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS) were used for the analyses of two major peaks and one minor peak in product A and two major peaks in product B. These five compounds were isolated by silica gel column chromatography, and their structures were analyzed by <sup>1</sup>H, <sup>13</sup>C-NMR and various two-dimensional NMR techniques, i.e., H-H correlation spectroscopy, heteronuclear multiple quantum coherence, heteronuclear multiple-bond correlation, and nuclear Overhauser effect spectroscopy.</p><p><strong>Results: </strong>Three compounds isolated from product A were identified as rel-(6aR,9R,10aR)-hexahydrocannabinol (11β-hexahydrocannabinol; 11β-HHC), rel-(6aR,9S,10aR)-hexahydrocannabinol (11α-hexahydrocannabinol, 11α-HHC), and a minor compound (2R,5S,6R)-dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC). Meanwhile, the structural isomers of the major compound isolated from product B were identified as rel-(6aR, 9R, 10aR)-hexahydrocannabiphorol (11β-hexahydrocannabiphorol; 11β-HHCP) and rel-(6aR, 9S, 10aR)-hexahydrocannabiphorol (11α-hexahydrocannabiphorol; 11α-HHCP).</p><p><strong>Conclusions: </strong>The presence of both 11β-HHC and 11α-HHC in the HHC products analyzed in this study suggests that they were most likely synthesized via the reduction reaction of Δ<sup>8</sup>-THC or Δ<sup>9</sup>-THC. Dihydro-iso-THC was probably obtained as a byproduct of the synthesis of Δ<sup>8</sup>-THC or Δ<sup>9</sup>-THC from cannabidiol. Similarly, 11β-HHCP and 11α-HHCP in the HHCP product could stem from Δ<sup>9</sup>-tetrahydrocannabiphorol.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.8000,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Identification of hexahydrocannabinol (HHC), dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC) and hexahydrocannabiphorol (HHCP) in electronic cigarette cartridge products.\",\"authors\":\"Rie Tanaka, Ruri Kikura-Hanajiri\",\"doi\":\"10.1007/s11419-023-00667-9\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><strong>Purpose: </strong>Since 2021, products claiming to contain hexahydrocannabinol (HHC) and hexahydrocannabiphorol (HHCP), which are tetrahydrocannabinol (THC) analogs, have been distributed via the Internet. Owing to the presence of three asymmetric carbons in their structure, HHC and HHCP have multiple stereoisomers. This study aimed to identify the actual stereoisomers of HHC and HHCP isolated from electronic cigarette cartridge products using nuclear magnetic resonance (NMR) spectroscopy.</p><p><strong>Methods: </strong>Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS) were used for the analyses of two major peaks and one minor peak in product A and two major peaks in product B. These five compounds were isolated by silica gel column chromatography, and their structures were analyzed by <sup>1</sup>H, <sup>13</sup>C-NMR and various two-dimensional NMR techniques, i.e., H-H correlation spectroscopy, heteronuclear multiple quantum coherence, heteronuclear multiple-bond correlation, and nuclear Overhauser effect spectroscopy.</p><p><strong>Results: </strong>Three compounds isolated from product A were identified as rel-(6aR,9R,10aR)-hexahydrocannabinol (11β-hexahydrocannabinol; 11β-HHC), rel-(6aR,9S,10aR)-hexahydrocannabinol (11α-hexahydrocannabinol, 11α-HHC), and a minor compound (2R,5S,6R)-dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC). Meanwhile, the structural isomers of the major compound isolated from product B were identified as rel-(6aR, 9R, 10aR)-hexahydrocannabiphorol (11β-hexahydrocannabiphorol; 11β-HHCP) and rel-(6aR, 9S, 10aR)-hexahydrocannabiphorol (11α-hexahydrocannabiphorol; 11α-HHCP).</p><p><strong>Conclusions: </strong>The presence of both 11β-HHC and 11α-HHC in the HHC products analyzed in this study suggests that they were most likely synthesized via the reduction reaction of Δ<sup>8</sup>-THC or Δ<sup>9</sup>-THC. Dihydro-iso-THC was probably obtained as a byproduct of the synthesis of Δ<sup>8</sup>-THC or Δ<sup>9</sup>-THC from cannabidiol. Similarly, 11β-HHCP and 11α-HHCP in the HHCP product could stem from Δ<sup>9</sup>-tetrahydrocannabiphorol.</p>\",\"PeriodicalId\":12329,\"journal\":{\"name\":\"Forensic Toxicology\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.8000,\"publicationDate\":\"2024-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Forensic Toxicology\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://doi.org/10.1007/s11419-023-00667-9\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2023/6/26 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"TOXICOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Forensic Toxicology","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1007/s11419-023-00667-9","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2023/6/26 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"TOXICOLOGY","Score":null,"Total":0}
引用次数: 0
摘要
目的：自 2021 年以来，声称含有六氢大麻酚（HHC）和六氢大麻酚（HHCP） （四氢大麻酚类似物）的产品一直通过互联网销售。由于其结构中存在三个不对称碳，HHC 和 HHCP 具有多种立体异构体。本研究旨在利用核磁共振（NMR）光谱鉴定从电子烟盒产品中分离出的 HHC 和 HHCP 的实际立体异构体：采用气相色谱-质谱法（GC-MS）和液相色谱-光电二极管阵列质谱法（LC-PDA-MS）分析了产品 A 中的两个主要峰和一个次要峰，以及产品 B 中的两个主要峰、结果：结果：从产物 A 中分离出的三种化合物被鉴定为 rel-(6aR,9R,10aR)-六氢大麻酚（11β-hexahydrocannabinol；11β-HHC）、rel-(6aR,9S,10aR)-六氢大麻酚（11α-hexahydrocannabinol，11α-HHC）和一种次要化合物 (2R,5S,6R)-二氢-异四氢大麻酚（二氢-异-THC）。同时，从产物 B 中分离出的主要化合物的结构异构体被鉴定为 rel-（6aR，9R，10aR）-六氢大麻酚（11β-hexahydrocannabiphorol；11β-HHCP）和 rel-（6aR，9S，10aR）-六氢大麻酚（11α-hexahydrocannabiphorol；11α-HHCP）：结论：本研究分析的 HHC 产品中同时存在 11β-HHC 和 11α-HHC 这两种物质，表明它们很可能是通过 Δ8-THC 或 Δ9-THC 的还原反应合成的。二氢异四氢大麻酚可能是由Δ8-四氢大麻酚或Δ9-四氢大麻酚合成的副产品。同样，HHCP 产品中的 11β-HHCP 和 11α-HHCP 可能来自 Δ9-四氢大麻酚。
Identification of hexahydrocannabinol (HHC), dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC) and hexahydrocannabiphorol (HHCP) in electronic cigarette cartridge products.
Purpose: Since 2021, products claiming to contain hexahydrocannabinol (HHC) and hexahydrocannabiphorol (HHCP), which are tetrahydrocannabinol (THC) analogs, have been distributed via the Internet. Owing to the presence of three asymmetric carbons in their structure, HHC and HHCP have multiple stereoisomers. This study aimed to identify the actual stereoisomers of HHC and HHCP isolated from electronic cigarette cartridge products using nuclear magnetic resonance (NMR) spectroscopy.
Methods: Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS) were used for the analyses of two major peaks and one minor peak in product A and two major peaks in product B. These five compounds were isolated by silica gel column chromatography, and their structures were analyzed by 1H, 13C-NMR and various two-dimensional NMR techniques, i.e., H-H correlation spectroscopy, heteronuclear multiple quantum coherence, heteronuclear multiple-bond correlation, and nuclear Overhauser effect spectroscopy.
Results: Three compounds isolated from product A were identified as rel-(6aR,9R,10aR)-hexahydrocannabinol (11β-hexahydrocannabinol; 11β-HHC), rel-(6aR,9S,10aR)-hexahydrocannabinol (11α-hexahydrocannabinol, 11α-HHC), and a minor compound (2R,5S,6R)-dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC). Meanwhile, the structural isomers of the major compound isolated from product B were identified as rel-(6aR, 9R, 10aR)-hexahydrocannabiphorol (11β-hexahydrocannabiphorol; 11β-HHCP) and rel-(6aR, 9S, 10aR)-hexahydrocannabiphorol (11α-hexahydrocannabiphorol; 11α-HHCP).
Conclusions: The presence of both 11β-HHC and 11α-HHC in the HHC products analyzed in this study suggests that they were most likely synthesized via the reduction reaction of Δ8-THC or Δ9-THC. Dihydro-iso-THC was probably obtained as a byproduct of the synthesis of Δ8-THC or Δ9-THC from cannabidiol. Similarly, 11β-HHCP and 11α-HHCP in the HHCP product could stem from Δ9-tetrahydrocannabiphorol.
期刊介绍：
The journal Forensic Toxicology provides an international forum for publication of studies on toxic substances, drugs of abuse, doping agents, chemical warfare agents, and their metabolisms and analyses, which are related to laws and ethics. It includes original articles, reviews, mini-reviews, short communications, and case reports. Although a major focus of the journal is on the development or improvement of analytical methods for the above-mentioned chemicals in human matrices, appropriate studies with animal experiments are also published.
Forensic Toxicology is the official publication of the Japanese Association of Forensic Toxicology (JAFT) and is the continuation of the Japanese Journal of Forensic Toxicology (ISSN 0915-9606).
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