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S0752

Sigma-Aldrich

(±)-Synephrine

≥98%

Synonym(s):

1-(4-Hydroxyphenyl)-2-methylaminoethanol, 4-Hydroxy-α-(methylaminomethyl)benzyl alcohol

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About This Item

Linear Formula:
HOC6H4CH(CH2NHCH3)OH
CAS Number:
94-07-5
Molecular Weight:
167.21
EC Number:
202-300-9
MDL number:
MFCD00002370
UNSPSC Code:
41116107
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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Katsuhisa Ozaki et al.
Nature communications, 2, 542-542 (2011-11-17)
Swallowtail butterflies belonging to the family of Papilionidae selectively utilize a limited number of plants from a single or a few families. Female butterflies lay eggs on their host only when they detect specific chemicals through their foreleg chemosensilla while
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 M Brown et al.
British journal of pharmacology, 93(2), 417-429 (1988-02-01)
1. The activities of the (-)- and (+)-forms of m- and p-octopamine and m- and p-synephrine on alpha 1-adrenoceptors from rat aorta and anococcygeus and alpha 2-adrenoceptors from rabbit saphenous vein were compared with those of noradrenaline (NA). 2. The
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
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