Structure of cannabidiol, a product isolated from the marihuana extract of Minnesota wild hemp I

Structure of cannabidiol, a product isolated from the marihuana extract of Minnesota wild hemp I
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DOI:
10.1021/ja01858a058
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发表时间:
1940-01-01
影响因子:
15
通讯作者:
Clark, JH
Clark, JH
中科院分区:
化学1区
文献类型:
--
作者:
Adams, R;Hunt, M;Clark, JH

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大麻是美国常用的术语,代表大麻或大麻植物中能够引起人类躯体和精神变化的部分。它也被称为“大麻”、“bhang”、“charas”和“ganja”。人们发现该植物提取物的活性差异很大,并且取决于大麻的来源。以前的研究人员大部分都研究了通过处理印度大麻品种(称为印度大麻)的大麻而获得的树脂。在这项调查中,明尼苏达州的野生大麻被用作原材料,在开花后、种子在雌性顶部“凝固”之前被砍伐。用乙醇提取,并通过减压蒸馏获得含有有效成分的所谓“红油”。许多研究人员研究了来自大麻和籼稻的活性红油,但尚未从现有产品的混合物中分离出除正二十烷以外的单一纯物质。 Wood、Spivey 和 Easterfield 将其称为大麻酚 2,并通过其结晶醋酸盐进行纯化。他们指定的化学式为 C21H26O2。 Cahn 3 证实了该式并对其构成进行了研究,他提出了结构 I,其中羟基和正戊基的位置不确定。
Marihuana is the term commonly used in the United States to represent those portions of the Cannabis sativa or hemp plant which are capable of inducing somatic and psychic changes in hu-mans. It is also familiarly known as hashish, bhang, charas, and ganja. The activity of an extract of the plant is found to vary widely, andto be dependent on the source of the hemp. Pre-vious investigators, for the most part, have studied the resin obtained by workingup hashish of Indian origin from the variety of hemp known as Cannabis indica. Inthis investigation, Minnesota wild hemp, cut after floweringhad begun and before the seed had “set” in the femále tops, was used as a raw material. It was extracted with ethanol and the so-called “red oil” containing the active principle or principles was obtained by distillation under diminished pressure. Numerous investigators have studied the active red oil from Cannabis sativa andindica but only a single pure substance otherthan nonacosane has yet been isolated from the mixture of products present. This was called cannabinol by Wood, Spivey and Easterfield, 2 and was purified through its crystalline acetate. They assigned the formula C21H26O2. This formula was confirmed and the constitution investigated by Cahn, 3 who pro-posed structureI in which the positions of the hydroxyl and w-amyl groups are uncertain.