synephrine
benzenemethanol, 4-hydroxy-a-((methylamino)methyl)- (9CI)
Identification
| Name | synephrine |
| CAS Number | 94-07-5 |
| EINECS | 202-300-9 |
| FDA UNII | PEG5DP7434 |
| Molecular Formula | C9 H13 N O2 |
| Molecular Weight | 167.20801000 |
| MDL Number | MFCD00002370 |
| Nikkaji Number | J8.617G |
| Beilstein | 1103010 |
| XlogP3 | -0.60 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 184.50 °C. @ 760.00 mm Hg |
| Boiling Point | 341.07 °C. @ 760.00 mm Hg (est) |
| Flash Point | 326.00 °F. TCC ( 163.40 °C. ) (est) |
| logP (o/w) | -0.450 |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 1000 mg/kg |
| Dermal Toxicity | subcutaneous-mouse LDLo 1500 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for synephrine usage levels up to | not for fragrance use. |
| Recommendation for synephrine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
benzenemethanol, 4-hydroxy-a-((methylamino)methyl)-
benzenemethanol, 4-hydroxy-a-((methylamino)methyl)- (9CI)
benzenemethanol, 4-hydroxy-a-[ (methylamino)methyl]-
benzenemethanol, 4-hydroxy-a-[(methylamino)methyl]-
benzyl alcohol, p-hydroxy-a-[ (methylamino)methyl]-
benzyl alcohol, p-hydroxy-a-[(methylamino)methyl]-
4-(1-
hydroxy-2-(methylamino)ethyl)phenol
4-[1-
hydroxy-2-(methylamino)ethyl]phenol
4-
hydroxy-a-((methylamino)methyl)benzenemethanol
p-
hydroxy-a-((methylamino)methyl)benzyl alcohol
4-
hydroxy-a-(methylaminomethyl)benzyl alcohol
4-
hydroxy-a-[(methylamino)methyl]benzenemethanol
hydroxy-a-[(methylamino)methyl]benzyl alcohol
p-
hydroxy-a-[(methylamino)methyl]benzyl alcohol
p-
hydroxy-a-[(methylamino)methyl]benzylalcohol
1-(4-
hydroxyphenyl)-(N-methylethanol)amine
1-(4-
hydroxyphenyl)-2-(methylamino)ethan-1-ol
1-(4-
hydroxyphenyl)-2-(methylamino)ethanol
1-(4-
hydroxyphenyl)-2-methylaminoethanol
b-
methylamino-a-(4-hydroxyphenyl)ethyl Alcobol
p-[(
methylamino)ethanol]phenol
[(
methylamino)methyl][(4-hydroxyphenyl)carbinol]
methylaminomethyl 4-hydroxyphenyl carbinol
parasympatol
simpadren
sympaethamine
sympathol
(±)-
synephrine
p-
synephrine
PubMed:
Metabolite Signature of Candidatus Liberibacter asiaticus Infection in Two Citrus Varieties.
PubMed:
A cocktail of synthetic stimulants found in a dietary supplement associated with serious adverse events.
PubMed:
p-Synephrine: a novel agonist for neuromedin U2 receptor.
PubMed:
A novel molecularly imprinted polymer of the specific ionic liquid monomer for selective separation of synephrine from methanol-water media.
PubMed:
Citrus aurantium and Rhodiola rosea in combination reduce visceral white adipose tissue and increase hypothalamic norepinephrine in a rat model of diet-induced obesity.
PubMed:
Synephrine-containing dietary supplement precipitating apical ballooning syndrome in a young female.
PubMed:
High-performance liquid chromatographic analysis of biogenic amines in pharmaceutical products containing Citrus aurantium.
PubMed:
Cardiovascular toxicity of Citrus aurantium in exercised rats.
PubMed:
A 60day double-blind, placebo-controlled safety study involving Citrus aurantium (bitter orange) extract.
PubMed:
Phytochemical profile and antioxidant activity of physiological drop of citrus fruits.
PubMed:
Study of the photocatalytic transformation of synephrine: a biogenic amine relevant in anti-doping analysis.
PubMed:
Physiological effects following administration of Citrus aurantium for 28 days in rats.
PubMed:
Detection of hazardous weight-loss substances in adulterated slimming formulations using ultra-high-pressure liquid chromatography with diode-array detection.
PubMed:
[Determination of synephrine and arecoline contents in Xiao'er Xiaoji Zhike oral liquid].
PubMed:
Simultaneous determination of flavanones, hydroxycinnamic acids and alkaloids in citrus fruits by HPLC-DAD-ESI/MS.
PubMed:
Developmental toxicity of Citrus aurantium in rats.
PubMed:
The safety of Citrus aurantium (bitter orange) and its primary protoalkaloid p-synephrine.
PubMed:
Synephrine: from trace concentrations to massive consumption in weight-loss.
PubMed:
Rapid simultaneous determination of amines and organic acids in citrus using high-performance liquid chromatography.
PubMed:
Synephrine: from trace concentrations to massive consumption in weight-loss.
PubMed:
Experience (mostly negative) with the use of sympathomimetic agents for weight loss.
PubMed:
Fast CE analysis of adrenergic amines in different parts of Citrus aurantium fruit and dietary supplements.
PubMed:
Analysis of adulterated herbal medicines and dietary supplements marketed for weight loss by DOSY 1H-NMR.
PubMed:
Influence of different organic fertilizers on quality parameters and the delta(15)N, delta(13)C, delta(2)H, delta(34)S, and delta(18)O values of orange fruit (Citrus sinensis L. Osbeck).
PubMed:
STEMI in a 24-year-old man after use of a synephrine-containing dietary supplement: a case report and review of the literature.
PubMed:
Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.
PubMed:
Synephrine content of juice from Satsuma mandarins (Citrus unshiu Marcovitch).
PubMed:
Concentrations of p-synephrine in fruits and leaves of Citrus species (Rutaceae) and the acute toxicity testing of Citrus aurantium extract and p-synephrine.
PubMed:
Lipolysis induced by segment wall extract from Satsuma mandarin orange (Citrus unshu Mark).
PubMed:
Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium).
PubMed:
Simultaneous analysis of adrenergic amines and flavonoids in citrus peel jams and fruit juices by liquid chromatography: part 2.
PubMed:
Analysis of ephedra-free labeled dietary supplements sold in the San Francisco Bay area in 2003.
PubMed:
A new method for fabrication of an integrated indium tin oxide electrode on electrophoresis microchips with amperometric detection and its application for determination of synephrine and hesperidin in pericarpium citri reticulatae.
PubMed:
Consumption of dietary supplements containing Citrus aurantium (bitter orange)--2004 California Behavioral Risk Factor Surveillance Survey (BRFSS).
PubMed:
A rapid and simple procedure for the determination of synephrine in dietary supplements by gas chromatography-mass spectrometry.
PubMed:
Variant angina associated with bitter orange in a dietary supplement.
PubMed:
An isotopically labeled internal standard liquid chromatography-tandem mass spectrometry method for determination of ephedrine alkaloids and synephrine in dietary supplements.
PubMed:
A rapid liquid chromatography electrospray ionization mass spectrometry(n) method for evaluation of synephrine in Citrus aurantium L. samples.
PubMed:
Determination of ephedrine alkaloids in dietary supplement standard reference materials.
PubMed:
Nitrogen metabolism components as a tool to discriminate between organic and conventional citrus fruits.
PubMed:
Molecular mechanisms of toxicity of important food-borne phytotoxins.
PubMed:
Moderate weight-lowering effect of octopamine treatment in obese Zucker rats.
PubMed:
Ephedra-free is not danger-free.
PubMed:
Determination of ephedrine alkaloids and synephrine in dietary supplements by column-switching cation exchange high-performance liquid chromatography with scanning-wavelength ultraviolet and fluorescence detection.
PubMed:
Determination of Synephrine Enantiomers in Food and Conjugated Synephrine in Urine by High-Performance Liquid Chromatography with Electrochemical Detection
PubMed:
Determination of synephrine enantiomers in food and conjugated synephrine in urine by high-performance liquid chromatography with electrochemical detection.