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

• ChemBase ID: 4444
• Molecular Formular: C9H13NO3
• Molecular Mass: 183.20442
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol
• IUPAC Traditional name: α-methylnoradrenaline; levonordefrin
• Brand Name: Nordefrin
• Synonyms: 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; (-)-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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.634196
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.68648
• LogD (pH = 7.4): -1.602401
• Log P: -0.39267403
• Molar Refractivity: 48.8745 cm^3
• Polarizability: 19.21334 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.77
• LOG S: -1.1
• Solubility (Water): 1.46e+01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Water
• Apperance: White to Off-White Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... ADRB2(154)rat ... Adra1a(29412), Adra2a(25083)

Product Information

• Purity: ≥90%
• Grade: analytical standard, for drug analysis

DETAILS

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.

REFERENCES

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