synephrine
benzenemethanol, 4-hydroxy-a-((methylamino)methyl)- (9CI)
 
Notes:
sympathetic alpha-adrenergic agonist with actions like phenylephrine. it is used as a vasoconstrictor in circulatory failure, asthma, nasal congestion, and glaucoma. A widely distributed alkaloid, occurs in citrus leaves and juice and other plants R-Synephrine is the form found in nature. Synephrine (or oxedrine) is a drug commonly used for weight loss. While its effectiveness is widely debated, synephrine has gained significant popularity as an alternative to ephedrine, a related substance which has been made illegal or restricted in many countries due to its use as a precursor in the illicit manufacture of methamphetamine. Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions [citation needed]. Synephrine is derived primarily from the fruit of Citrus aurantium, a relatively small citrus tree, of which several of its more common names include Bitter Orange, Sour Orange, and Zhi shi.; There has been some confusion surrounding synephrine and phenylephrine (neosynephrine), one of its positional isomers. The chemicals are similar in structure; the only difference is the location of the aromatic hydroxyl group. In synephrine, the hydroxyl is at the para position, whereas, in neosynephrine, it is at the meta position. Each compound has differing biological properties.; p-Synephrine is an endogenous amine in plasma, in variable levels with a tendency to be higher in hypertensive patients (PMID 8255371)
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      Product(s):
      94-07-5 Synephrine >98%
      Synephrine, that can be extracted from the young fruits Citrus aurantium L, is a drug product in Europe that was originally produced as a synthetic derivative of amphetamine for use as a sympathomimetic. Anti-allergy/anti-virus/anti-inflammatory
       
       
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CAS Number: 94-07-5Picture of molecule3D/inchi
Other(deleted CASRN): 582-84-3
ECHA EINECS - REACH Pre-Reg: 202-300-9
FDA UNII: PEG5DP7434
Nikkaji Web: J8.617G
Beilstein Number: 1103010
MDL: MFCD00002370
XlogP3: -0.60 (est)
Molecular Weight: 167.20801000
Formula: C9 H13 N O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Alfa Biotechnology
For experimental / research use only.
Synephrine 98%
BOC Sciences
For experimental / research use only.
Synephrine >98%
Odor: characteristic
Use: Synephrine, that can be extracted from the young fruits Citrus aurantium L, is a drug product in Europe that was originally produced as a synthetic derivative of amphetamine for use as a sympathomimetic. Anti-allergy/anti-virus/anti-inflammatory
Changsha Organic Herb
Citrus Aurantium Extract
Santa Cruz Biotechnology
For experimental / research use only.
(+/-)-Synephrine
Sigma-Aldrich: Sigma
For experimental / research use only.
(±)-Synephrine ≥98%
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50  1000 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 89, Pg. 297, 1947.

intravenous-mouse LD50  270 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 341, 1952.

intravenous-rabbit LDLo  150 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 101, Pg. 81, 1955.

Dermal Toxicity:
subcutaneous-mouse LDLo 1500 mg/kg
SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 136, Pg. 172, 1928.

subcutaneous-rat LDLo 1500 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 101, Pg. 81, 1955.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
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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Safety References:
European Food Safety Authority (EFSA) reference(s):
Scientific Opinion on the safety of caffeine
View page or View pdf
EPI System: View
ClinicalTrials.gov: search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 7172
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 4-[1-hydroxy-2-(methylamino)ethyl]phenol
Chemidplus: 0000094075
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References:
 4-[1-hydroxy-2-(methylamino)ethyl]phenol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 7172
Pubchem (sid): 134970800
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C04548
HMDB (The Human Metabolome Database): HMDB04826
FooDB: FDB000709
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 citrus juice
Search  PMC Picture
 lemon leaf
Search Trop  Picture
 lemon pericarp
Search Trop  Picture
 mandarin fruit
Search Trop  Picture
 mandarin pericarp
Search Trop  Picture
 orange fruit
Search Trop  Picture
 orange pericarp
Search Trop  Picture
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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
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Articles:
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.
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