ヨヒンビン
(+)-17α-ヒドロキシヨヒンバン-16α-カルボン酸メチル · アフロジン · (+)-ヨヒンビン · クエブラキン · 17α-ヒドロキシヨヒンバン-16α-カルボン酸メチル · コリニン · ヨヒンビン · Yohimbin
識別子と物理属性
| CAS No. | 146-48-5 |
|---|---|
| 分子式 | C21H26N2O3 |
| 平均分子量 | 354.4 g/mol |
| 単同位体質量 | 354.19434269 g/mol |
| SMILES | COC(=O)[C@@H]1[C@H]2C[C@H]3c4[nH]c5ccccc5c4CCN3C[C@@H]2CC[C@@H]1O |
| InChIKey | BLGXFZZNTVWLAY-SCYLSFHTSA-N |
| PubChem CID | 8969 |
| ChEMBL | CHEMBL15245 |
| ChEBI | CHEBI:10093 |
| EC No. | 205-672-0 |
| DTXSID | DTXSID9040130 |
| 現地名 | ヨヒンビン |
化学・物理的性質
| XLogP | 2.9 |
|---|---|
| 極性表面積 | 65.6 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 2 |
| 重原子数 | 26 |
| 形式電荷 | 0 |
| 複雑度 | 555 |
| 医薬品 | DEA NFLIS-Drug Category -> HallucinogensPharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Crystal structure |
| LogP（分配係数） | 2.732.01 |
| 溶解度 | 3.48e-01 g/LTHFDMSOクロロホルム |
| Human Drugs | Pharmaceuticals |
| 融点 | 241 °C231-233 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 189.51 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]186.5 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| 比旋光度 | D20 +50.9 to +62.2° (ethanol)D20 +108° (pyridine)20546 +129° (c = 0.5 in pyridine) |
| 沸点 | 487.66°C (rough estimate) |
| 密度 | 1.1640 (rough estimate) |
| 屈折率 | 1.6500 (estimate) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 14.39±0.40(Predicted) |
| 色 | ベージュ |
| InChIKey | BLGXFZZNTVWLAY-SCYLSFHTSA-N |
| SMILES | [C@@H]1(O)[C@H](C(OC)=O)[C@]2(C[C@@]3(N(C[C@@]2(CC1)[H])CCC1C2=C(NC3=1)C=CC=C2)[H])[H] |
| LogP（分配係数） | 2.730 |
| CAS データベース | 146-48-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Yohimbine(146-48-5) |
化学的特性
Glistening, needle-like alkaloid, soluble in alcohol and ether, very slightly soluble in water.
安全性と法規制
| GHS 分類 | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 27 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Regulation (EC) No 178/2002 (amended)Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.alpha.,17.alpha.)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| その他の安全情報 | IMAP assessments - Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.alpha.,17.alpha.)-: Human health tier I assessment |
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Hepatotoxicity | In small clinical trials and case series, yohimbine therapy has not been linked to serum enzyme elevations or clinical liver disease. Although yohimbine is often found in weight loss and muscle building herbal combinations, it has not been associated with cases of clinically apparent acute liver injury. |
| RTECS 番号 | ZG1000000 |
| 輸送番号（UN） | 1544 |
| 危険文句（R） | 23/24/25-39 |
| 危険表示 | T |
| 安全措置（S） | 27-36/37/39-45 |
| 危険等級 | 6.1(a) |
| 包装等級 | II |
用途
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）
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.
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 10weeks. 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.
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.
製法・合成法
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