4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol

• ChemBase编号: 4444
• 分子式: C9H13NO3
• 平均质量: 183.20442
• 单一同位素质量: 183.08954328
• SMILES: C[C@@H]([C@@H](c1cc(c(cc1)O)O)O)N
• Canonical SMILES: C[C@@H]([C@@H](c1ccc(c(c1)O)O)O)N
• InChI: InChI=1S/C9H13NO3/c1-5(10)9(13)6-2-3-7(11)8(12)4-6/h2-5,9,11-13H,10H2,1H3/t5-,9-/m0/s1
• InChIKey: GEFQWZLICWMTKF-CDUCUWFYSA-N

名称和登记号

名称

• IUPAC标准名: 4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol
• IUPAC传统名: α-methylnoradrenaline; levonordefrin
• 商标名: Nordefrin
• 别名: (-)-α-甲基去甲肾上腺素; 4-(2-氨基-1-羟基丙基)苯-1,2-二醇; L-4-(2-氨基-1-羟丙基)-1,2-苯二醇; 左旋异肾上腺素; 异肾上腺素; (-)-3,4-二羟基去甲麻黄碱; Levonordefrin; (-)-3,4-Dihydroxynorephedrine; 4-[(1R,2S)-2-Amino-1-hydroxypropyl]-1,2-benzenediol; BA 2818; Corbadrine; D-(-)-Cobefrin; L-α-Methylnoradrenaline; Levonordefrin; Neo-cobefrin; l-Cobefrin; (-)-Nordefrin; (-)-3,4-Dihydroxy Norephedrine

登记号

• CAS号: 829-74-3
• MDL号: MFCD00134415
• PubChem SID: 99443259; 24277784; 160967876
• PubChem CID: 164739

理论计算性质

JChem

• Acid pKa: 9.634196
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -2.68648
• LogD (pH = 7.4): -1.602401
• Log P: -0.39267403
• 摩尔折射率: 48.8745 cm^3
• 极化性: 19.21334 Å^3
• 极化表面积: 86.71 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.77
• LOG S: -1.1
• 溶解度: 1.46e+01 g/l

分子性质

理化性质

• 溶解度: DMSO; Hot Water
• 外观: White to Off-White Solid
• 熔点: >200°C (dec.)

安全信息

• 保存条件: -20°C Freezer
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22-36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H315-H319-H332-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... ADRB2(154)rat ... Adra1a(29412), Adra2a(25083)

产品相关信息

• 纯度: ≥90%
• 级别: analytical standard, for drug analysis

详细说明

DrugBank - DB06707

• Drug Groups: approved
• Description: Levonordefrin acts as a topical nasal decongestant and vasoconstrictor, most often used in dentistry.
• Indication: Used as a topical nasal decongestant and vasoconstrictor in dentistry.
• Pharmacology: is a sympathomimetic amine used as a vasoconstrictor in local; anesthetic solutions. It has pharmacologic activity similar to that of Epinephrine but it is more stable than Epinephrine. In equal concentrations, Levonordefrin is less potent than Epinephrine in raising blood pressure, and as a vasoconstrictor.
• External Links: Wikipedia

Sigma Aldrich - D5290

Biochem/physiol Actions
肾上腺素激动剂；血管收缩剂。

Toronto Research Chemicals - D454000

A vasoconstrictor which also increases the potency and duration of anesthesia produced by local anesthetics.

参考文献

• Luduena, F.P., et al.: J. Dent. Res., 37, 206 (1958)
• Farrugia, M.T., et al.: J. Pharm. Pharmac., 21, 199 (1969)