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Safety Information

S0752

Sigma-Aldrich

(±)-Synephrine

≥98%

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Synonym(s):
1-(4-Hydroxyphenyl)-2-methylaminoethanol, 4-Hydroxy-α-(methylaminomethyl)benzyl alcohol
Linear Formula:
HOC6H4CH(CH2NHCH3)OH
CAS Number:
94-07-5
Molecular Weight:
167.21
EC Number:
202-300-9
MDL number:
MFCD00002370
UNSPSC Code:
12352200
PubChem Substance ID:
24278691
NACRES:
NA.77

Assay

≥98%

mp

187 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

OC1=CC=C(C(O)CNC)C=C1

InChI

1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3

InChI key

YRCWQPVGYLYSOX-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152)

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Application

(±)-Synephrine has been used as an alkaloid to investigate its in vitro antiviral, antibacterial, antifungal and cytotoxicity activities.

Biochem/physiol Actions

Synephrine is naturally found in citrus plants belonging to the Rutaceae family. It is a sympathomimetic alkaloid. Synephrine has 3 isomeric forms, such as m-synephrine, p-synephrine and o-synephrine. It exhibits β-adrenergic properties.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Claudio Medana et al.
Analytical and bioanalytical chemistry, 405(2-3), 1105-1113 (2012-12-05)
The occurrence of some cases of positive results in anti-doping analysis of octopamine requires clarification as to whether its methylated derivative synephrine could be a metabolic precursor of octopamine itself. Synephrine is a natural phenylethylamine derivative present in some food
Jie-Ping Fan et al.
Analytical and bioanalytical chemistry, 402(3), 1337-1346 (2011-11-17)
In this work, molecularly imprinted solid-phase extraction (MISPE) has been used to selectively enrich, purify, or remove synephrine from Aurantii Fructus Immaturus. To this end, a molecularly imprinted polymer (MIP) was prepared by self-assembly from the template synephrine, the functional
Shun-ichi Ishiuchi et al.
The journal of physical chemistry. A, 115(37), 10363-10369 (2011-08-09)
In our previous work, we found that synephrine has six conformers in the gas phase, while adrenaline, which is a catecholamine and has the same side chain as synephrine, has been reported to have only two conformers. To determine the
C Carpéné et al.
Naunyn-Schmiedeberg's archives of pharmacology, 359(4), 310-321 (1999-05-27)
Numerous synthetic agonists selectively stimulate beta3-adrenoceptors (ARs). The endogenous catecholamines, noradrenaline and adrenaline, however, stimulate all the beta-AR subtypes, and no selective physiological agonist for beta3-ARs has been described so far. The aim of this study was to investigate whether
Luciana Grazziotin Rossato et al.
Archives of toxicology, 85(8), 929-939 (2010-12-09)
Synephrine is a natural compound, frequently added to ephedra-free dietary supplements for weight-loss, due to its effects as a nonspecific adrenergic agonist. Though only p-synephrine has been documented in plants, the presence of m-synephrine has also been reported in weight-loss
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