ホルデニン
アンハリン · ジメチル[2-(4-ヒドロキシフェニル)エチル]アミン · p-(2-ジメチルアミノエチル)フェノール · 4-[2-(ジメチルアミノ)エチル]フェノール · N,N-ジメチルチラミン · N,N-ジメチル-2-(4-ヒドロキシフェニル)エチルアミン · 4-ヒドロキシ-N,N-ジメチルベンゼンエタンアミン · 4-ヒドロキシ-N,N-ジメチルフェネチルアミン
識別子と物理属性
| CAS No. | 539-15-1 |
|---|---|
| 分子式 | C10H15NO |
| 平均分子量 | 165.23 g/mol |
| 単同位体質量 | 165.1153641 g/mol |
| SMILES | CN(C)CCc1ccc(O)cc1 |
| InChIKey | KUBCEEMXQZUPDQ-UHFFFAOYSA-N |
| PubChem CID | 68313 |
| ChEMBL | CHEMBL505789 |
| ChEBI | CHEBI:5764 |
| EC No. | 208-710-4 |
| DTXSID | DTXSID2046096 |
| 現地名 | ホルデニン |
化学・物理的性質
| XLogP | 2.1 |
|---|---|
| 極性表面積 | 23.5 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 3 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 117 |
| 医薬品 | Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds |
| 溶解度 | 7 mg/mLDMSO（微量）、メタノール（微量） |
| Human Drugs | Pharmaceuticals |
| 融点 | 117.5 °C117-118° |
| Physical Description | Solid |
| Collision Cross Section | 137.8 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| 沸点 | bp11 173° |
| 密度 | 1.0203 (rough estimate) |
| 屈折率 | 1.4820 (estimate) |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 外観・状態 | Solid |
| pKa（酸解離定数） | 10.05±0.26(Predicted) |
| 色 | ペールイエローからダークベージュ |
| Merck | 14,4746 |
| BRN | 2207615 |
| 主な用途 | メタボロミクスビタミン、栄養補助食品、天然製品 |
| 化粧品成分の機能 | 肌を保護する |
| InChI | 1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 |
| InChIKey | KUBCEEMXQZUPDQ-UHFFFAOYSA-N |
| SMILES | CN(C)CCc1ccc(O)cc1 || CN(C)CCc1ccc(O)cc1 |
| LogP（分配係数） | 1.400 (est) |
| CAS データベース | 539-15-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Phenol, 4-[2-(dimethylamino)ethyl]-(539-15-1) |
化学的特性
Light yellow solid
安全性と法規制
| GHS 分類 | WarningH302 (92.7%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (92.7%) |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29222990 |
| 危険文句（R） | 22-36-43 |
| 危険表示 | Xn |
| 安全措置（S） | 26-36/37 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
4-[2-(dimethylamino)ethyl]phenol．C10H15NO(165.23)．ホルデニン, アンハリンともいう．チラミンのN-ジメチル体．大麦の麦芽やサボテン科Anhalonium属植物，ビールなどに含まれている．フェネチルアルコールや4-(2-ヒドロキシエチル)アニソールから合成される．融点118 ℃，沸点173 ℃(1.46 kPa)．140～150 ℃ で昇華する．エタノール，クロロホルム，エーテルに易溶，水，ベンゼンに難溶．交感神経興奮薬に用いられる．森北出版「化学辞典（第2版）
説明
Hordenine (Item No. 21626) is a naturally occurring alkaloid found in a variety of plants, most commonly germinated barley (Hordeum species) from which the name is derived, and is structurally classified as a phenethylamine. It is biosynthesized by the step-wise double methylation of tyramine . Hordenine binds to and activates the dopamine D2 receptor (Ki = 13 μM) but antagonizes D2 receptor β-arrestin recruitment. It inhibits tyrosinase activity and expression at concentrations ≥ 50 μM resulting in reduced melanin accumulation in human melanocytes. Hordenine is present in significant amounts in beer and can be measured in serum in the free form, for up to 2 hours, and the glucuronidated form, for up to 6 hours, after beer consumption. This product is intended for research and forensic applications.
使用
Hordenine is suitable to study the effect of reed canary grass alkoloids on in vito digestibility. It is also suitable for use as a standard to identify endogenous hordenine in ungerminated and germinated barley by HPLC/diode array detection analysis. Hordenine may be used as an analytical reference material and in research on the activities of phenethylamine type alkaloids.
製法・合成法
純化方法
Crystallise Hordenine from EtOH or H2O and sublime it at 105o/5mm. The 4,4’-dichlorodiphenyl disulfimide salt has m 145-146o (from Me2CO/H2O) [Runge et al. Chem Ber 88 50 1955]. [Beilstein 13 H 626, 13 I 236, 13 II 356, 13 III 1640, 13 IV 1790.]