CAS 539-15-1 Hordenine (HCID 68313)

概要

Hordenine is a phenethylamine alkaloid. It has a role as a mouse metabolite and a human metabolite.

名称と識別子

優先名称: Hordenine
IUPAC: 4-[2-(dimethylamino)ethyl]phenol
現地名: ホルデニン
英語名: Hordenine
分子式: C10H15NO
分子量: 165.23

名称と別名

Hordenine539-15-14-[2-(Dimethylamino)ethyl]phenol4-(2-(Dimethylamino)ethyl)phenolAnhalineN,N-Dimethyltyramine4-(2-Dimethylaminoethyl)phenolPeyocactineAnhalinCactineEremursineOrdenina

名称をさらに表示

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ホルデニンHordeineHordeninHordetinOrdenineEremursin

p-(2-Dimethylaminoethyl)phenolDTXSID2046096K3489CA082CHEBI:5764DTXCID0026096N,N-Dimethyl-4-hydroxy-beta-phenethylamineRefChem:38568208-710-4

データベース識別子

CAS: 539-15-1
PubChem CID: 68313
DTXSID: DTXSID2046096
ChEMBL: CHEMBL505789
ChEBI: CHEBI:5764
UNII: K3489CA082
EC Number: 208-710-4
Nikkaji: J6.381I

物性

構造計算による物性

XLogP: 2.1
極性表面積: 23.5 Å²
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

実験および物理化学的性質

DrugsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Solubility7 mg/mL

Human DrugsPharmaceuticals

Melting Point117.5 °C

Physical DescriptionSolid

Collision Cross Section137.8 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

物理化学的性質

融点: 117 · 117-118°
沸点: 11 · bp11 173°
比重(密度): 1.0203 · 1.0203 (rough estimate)
屈折率: 1.482 · 1.4820 (estimate)
貯蔵温度: Inert atmosphere,Room Temperature
溶解性: DMSO（微量）、メタノール（微量）
外見: Solid
酸解離定数(Pka): 10.05 · 10.05±0.26(Predicted)
色: ペールイエローからダークベージュ
Merck: 14 · 14,4746
BRN: 2207615 · 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: 1.4 · 1.400 (est)
CAS データベース: 539 · 539-15-1(CAS DataBase Reference)
NISTの化学物質情報: 4 · Phenol, 4-[2-(dimethylamino)ethyl]-(539-15-1)

化学的性質

化学的特性Light yellow solid

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (92.7%)

安全データ

wgk: 3
hs_code: 29222990
risk_code: 22-36-43
hazard_code: Xn
safety_code: 26-36/37
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 11 - Combustible Solids

化学と産業

用途と製造

Use ClassificationPharmaceuticals

応用分野 · 3 件

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.

調製方法 · 1 件

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.]