ヨヒンビン 化学特性,用途語,生産方法
解説
ヨヒンビン,無色の針状晶．融点234 ℃．[α]D＋106°(ピリジン)．エタノール，クロロホルム，熱ベンゼンに可溶，エーテル，水に難溶．催淫(いん)作用があるので有名．適量で性器を充血させ，腰髄のぼっ起中枢に作用して，その機能を亢進させるが，多量ではめまい，けいれんを起こす．アドレナリン遮断剤で，塩酸塩として用いられる．
森北出版「化学辞典（第2版）
効能
α2アドレナリン受容体拮抗薬
存在
アカネ科Corynanthe yohimbeやキョウチクトウ科Rauwolfia serpentinaの樹皮に含まれるインドールアルカロイドの一種．
用途
適量で性器を充血させ，腰髄のぼっ起中枢に作用して，その機能を亢進させるが，多量ではめまい，けいれんを起こす．アドレナリン遮断剤で，塩酸塩として用いられる．
説明
Yohimbine is a natural alkaloid. It was first extracted from the barks of Corynanthe
yohimbe, a species of Rubiaceae trees in West Africa. It was reported that, in the
dried bark of Pausinystalia johimbe, the content of mixed alkaloids is higher than
6.1%, in which the main component is yohimbine, indicating a great prospect for
development . Yohimbe bark has been used as an aphrodisiac in Africa since
ancient times. In 1900, it was applied by Kowit and Muller to patients with impotence and paralytic insensitivity caused by neurasthenia and obtained curative effect.
From then on, clinical application of yohimbine began. Currently, yohimbine is a
pure plant preparation in the treatment of erectile dysfunction with more affirmation
and more applications.
化学的特性
Glistening, needle-like alkaloid, soluble in alcohol and ether, very slightly
soluble in water.
物理的性質
Appearance: white powder. Solubility: soluble in ethanol, chloroform, and hot benzene; slightly soluble in water and ether, usually salified by hydrochloric acid to
increase its solubility in water. Specific rotatory power (°): D22 +105° (in water).
Melting point: 241–246?°C.
来歴
Yohimbine has been used as an aphrodisiac for many years. At first, pharmacologists attributed its aphrodisiac effects to psychological effects similar to placebo or
increasement of peripheral vascular congestion, rather than real sexual stimulation.
Physiologists at the Stanford University first conducted a study on the pharmacological effects of yohimbine and found that yohimbine could increase the mating
ability of rats , which was then published on Science in 1984 . In addition,
researchers in the Queensland University in Canada conducted experiments on 23
patients with sexual dysfunction. Six of them recovered after taking the drug for
10?weeks. In 1987, Canadian scientists confirmed that yohimbine treatment in psychogenic impotence was safe and effective and this drug could restore the patient’ssexual ability . Besides, they proved that this medicine showed good curative
effects on organic impotence.
使用
Yohimbine occurs in Corinanthe johimbeK. and Rubiaceae trees. It is also foundin the roots of Rauwolfia serpentina L.and Apocyanaceae. Its derivatives areused therapeutically as adrenergic blockingagents.
定義
ChEBI: Yohimbine is an indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina. It has a role as an alpha-adrenergic antagonist, a serotonergic antagonist and a dopamine receptor D2 antagonist. It is functionally related to a yohimbic acid.
適応症
This product is listed in the 2017 edition of the British Pharmacopoeia, 40 editions
of the American Pharmacopoeia, and 9.0 edition of the European Pharmacopoeia.
The main clinical application of yohimbine includes tablets and injections. It is
mainly used to treat various types of impotence and sexual dysfunction in men.
一般的な説明
Yohimbine (Yocon)is a competitive and selective 2-blocker. The compound isan indolealkylamine alkaloid and is found in the bark of thetree Pausinystalia yohimbe and in Rauwolfia root.
健康ハザード
Pharmacologically, yohimbine is an adrenergic blocking agent. It exhibits hypotensive and cardiostimulant activities. Poisoningfrom excessive doses may become severe,causing convulsions and respiratory failure
LD50 value, intraperitoneal (mice): 16 mg/kg
LD50 value, oral (mice): 37 mg/kg.
生物活性
α 2 -adrenoceptor antagonist (pK i values are 8.52, 8.00 and 9.17 for human a 2A , a 2B and a 2C receptors respectively).
薬理学
Studies have shown that yohimbine has extensive pharmacological effects and has
been developed for the clinical treatment of arteriosclerosis, rheumatism, and other
diseases. The most obvious pharmacological action is in the treatment of male sexual dysfunction. Yohimbine tablets have been approved by the FDA and circulate in
international markets. Yohimbine can selectively block the presynaptic alpha 2
receptors and promote the release of norepinephrine . It stimulates more norepinephrine released by cavernous nerve endings and reduces reflux of phallic vein,
which is conducive to congestive erection. A small amount of application can make
the perineum swell and stimulate the erection center at the spinal cord, leading to
sexual hyperfunction . Yohimbine hydrochloride also has a psychological stimulant effect and increases libido. Like other types of adrenergic blocking drugs,
yohimbine’s resistance to adrenergic mediator in blood circulation is much stronger
than to sympathetic nerve impulse. Again, like tolazoline, yohimbine shows slight
effect in resisting adrenergic response in ocular smooth muscle. This drug does not
block the frequency and inotropic effects of epinephrine on mammalian hearts.
Yohimbine has minor direct effects on smooth muscle, and its effect on the central
nervous system is far less than that of ergot alkaloids, because yohimbine performs
an excited-to-paralyzed action. This drug produces diuretic effect, probably due to
the stimulation of the hypothalamus, resulting in release of posterior pituitary hormone. In addition, yohimbine has a significant local anesthetic effect .
臨床応用
Yohimbine increases heart rate and blood pressure as aresult of its blockade of 2-receptors in the CNS. It has beenused experimentally to treat male erectile impotence.
純化方法
Crystallise the alkaloid from EtOH, and dry it in a vacuum to remove EtOH of crystallisation. [Van Tamelen et al. J Am Chem Soc 91 7315 1969, Stork
Mode of action
Yohimbine is a selective α2-adrenergic antagonist. It is chemically similar to the alkaloid reserpine. Being a derivative of indolylalkylamine, it selectively blocks α2-adrenergic receptors. It weakens the negative feedback mechanism of norepinephrine release in nerve endings. It has a sympathomimetic effect, and can also cause sympathomimetic action. Additional research is evidently needed to conclusively delineate its pharmacological action.
ヨヒンビン 上流と下流の製品情報
原材料
Yohimban-16-carboxylic acid, 18,19-didehydro-17-hydroxy-, methyl ester, (16α,17α)-
(4aS)-4aα,5,7,8,13,13bβ,14,14aβ-オクタヒドロベンゾ[g]インドロ[2,3-a]キノリジン-2(1H)-オン
17-オキソヨヒンバン-16α-カルボン酸メチル
準備製品