4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride
Basic information
- CAS
5985-28-4- Standard SMILES
C[NH2+]CC(O)c1ccc(O)cc1.[Cl-]- InChIKey
COTCEGYSNTWJQV-UHFFFAOYSA-N- Molecular formula
- C9H14ClNO2
- Average molar mass
- 203.66 g/mol
- Monoisotopic mass
- 203.0713064
Overview
See also: Synephrine hydrochloride (preferred).
Names & identifiers
- Preferred name
- 4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride
- IUPAC
- [2-hydroxy-2-(4-hydroxyphenyl)ethyl]-methylazanium chloride
- English name
- Synephrine hydrochloride
- Molecular formula
- C9H14ClNO2
- Molecular weight
- 203.67
Names & synonyms
4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-methylazanium;chlorideSYNEPHRINE HCLJACS-5985-28-4UNII-EN5D1IH09SSynephrine HCl 98%minN-METHYL OCTOPAMINE HCLSympathol hydrochlorideSynephrine hydrochloridSYNEPHRINE HYDROCHLORIDESynephrine/Synephrine Hcl(±)-Oxedrine hydrochloride
Database identifiers
- CAS
5985-28-4- PubChem CID
- 22302
Properties
Computed structural properties
- Topological polar surface area
- 57.1 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 122
Physicochemical properties
- Melting point
- 147 · 147-150°C
- storage temp.
- Refrigerator
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- color
- Off-White to Pale Beige
- Cosmetics Ingredients Functions
- ANTIOXIDANTSKIN CONDITIONINGHAIR CONDITIONING
- InChI
- InChI=1S/C9H13NO2.ClH/c1-10-6-9(12)7-2-4-8(11)5-3-7;/h2-5,9-12H,6H2,1H3;1H
- InChIKey
- COTCEGYSNTWJQV-UHFFFAOYSA-N
- SMILES
- C1(=CC=C(O)C=C1)C(O)CNC.Cl
- LogP
- -0.03 · -0.030 (est)
- CAS DataBase Reference
- 5985 · 5985-28-4(CAS DataBase Reference)
- FDA UNII
- 5 D1IH09S · EN5D1IH09S
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H335-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- hs_code
- 2922498590
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H335-H319
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Applications
Description(±)-Synephrine is an alkaloid with vasoconstrictor and metabolic activities. It binds to α1A-, α2A-, and α2C-adrenergic receptors (ARs; Kis = 78, 36.7, and 24.4 μM, respectively). (±)-Synephrine is an agonist of α1A-ARs in HEK293 cells (EC50 = 4 μM in a reporter assay) but not in CHO cells expressing α2A- or α2C-AR. It also acts as an antagonist of α1A-, α2A-, and α2C-ARs, inhibiting L-phenylephrine-induced activation of α1A-AR in HEK293 cells and activation of α2A- and α2C-ARs induced by the α2-AR agonist medetomidine in CHO cells (IC50s = 12.8, 26, and 27.3 μM, respectively, in reporter assays). (±)-Synephrine induces contractions in isolated rabbit aortic rings (EC50 = 6.2 μg/ml) and increases ligation-induced mean arterial pressure in rats when administered at a dose of 2 mg/kg per day. It induces lipolysis in isolated rat and human adipocytes when used at concentrations of 100 and 1,000 μg/ml. (±)-Synephrine (50 μM) increases phosphorylation of Akt and AMP-activated protein kinase (AMPK) and translocation of Glut4 to the plasma membrane, as well as increases insulin-induced glucose consumption in L6 muscle cells when used at concentrations ranging from 25 to 200 μM.
UsesA α-adrenergic receptor agonist, vasoconstrictor.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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