Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, p.le A. Moro 5, 00185 Rome, Italy.
J Nat Prod. 2021 Sep 24;84(9):2502-2510. doi: 10.1021/acs.jnatprod.1c00513. Epub 2021 Jul 25.
The -stereoisomers of Δ-THC [(-)- and (+)-] were identified and quantified in a series of low-THC-containing varieties of registered in Europe as fiber hemp and in research accessions of cannabis. While Δ--THC () occurs in cannabis fiber hemp in the concentration range of (-)-Δ--THC [(-)-], it was undetectable in a sample of high-THC-containing medicinal cannabis. Natural Δ--THC () is scalemic (ca. 80-90% enantiomeric purity), and the absolute configuration of the major enantiomer was established as 6a,10a [(-)-] by chiral chromatographic comparison with a sample available by asymmetric synthesis. The major enantiomer, (-)-Δ--THC [(-)-], was characterized as a partial cannabinoid agonist in vitro and elicited a full tetrad response in mice at 50 mg/kg doses. The current legal discrimination between narcotic and non-narcotic cannabis varieties centers on the contents of "Δ-THC and isomers" and needs therefore revision, or at least a more specific wording, to account for the presence of Δ--THCs [(+)- and (-)-] in cannabis fiber hemp varieties.
在欧洲注册的一系列低 THC 含量品种的纤维大麻和大麻研究材料中，鉴定并定量了 Δ-THC 的立体异构体[（-）-和（+）-]。虽然 Δ--THC（）在大麻纤维大麻中的浓度范围为（-）-Δ--THC（-），但在高 THC 含量的药用大麻样本中无法检测到。天然 Δ--THC（）是手性的（约 80-90%对映体纯度），通过与通过不对称合成获得的样品的手性色谱比较，确定了主要对映体的绝对构型为 6a,10a[（-）-]。主要对映体（-）-Δ--THC（-）在体外表现为部分大麻素激动剂，在 50mg/kg 剂量下在小鼠中引起完全四氢大麻酚反应。目前对麻醉性和非麻醉性大麻品种的法律区分集中在“Δ-THC 和异构体”的含量上，因此需要修订，或者至少更具体的措辞，以说明纤维大麻品种中存在 Δ--THCs[（+）-和（-）-]。
