Showing Compound Synephrine (FDB001397)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:57 UTC

Update date

2018-05-28 23:05:53 UTC

Primary ID

FDB001397

Secondary Accession Numbers

FDB007966

Chemical Information

FooDB Name

Synephrine

Description

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).

CAS Number

94-07-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(+)-[(methylamino)Methyl]-benzenemethano	HMDB
(+)-P-Synephrine	HMDB
(+)-Synephrine	HMDB
(+/-)-synephrine	ChEBI
-Synephrine	Kegg
1-(4-Hydroxyphenyl)-2-(methylamino)ethanol	ChEBI
1-(4-Hydroxyphenyl)-2-methylaminoethanol	ChEBI
1-(p-Hydroxyphenyl)-2-methylaminoethanol	db_source
4-Hydroxy-a-[(methylamino)methyl]benzenemethanol	Generator
4-Hydroxy-a-[(methylamino)methyl]benzenemethanol, 9CI	db_source

Showing 1 to 10 of 33 entries

Predicted Properties

Property	Value	Source
Water Solubility	18.6 g/L	ALOGPS
logP	-0.62	ALOGPS
logP	-0.071	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.25 m³·mol⁻¹	ChemAxon
Polarizability	18.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H13NO2

IUPAC name

4-[1-hydroxy-2-(methylamino)ethyl]phenol

InChI Identifier

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

Isomeric SMILES

CNCC(O)C1=CC=C(O)C=C1

Average Molecular Weight

167.205

Monoisotopic Molecular Weight

167.094628665

Classification

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Organic oxygen compound
Aromatic alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:29081 )
ethanolamines (CHEBI:29081 )
phenethylamine alkaloid (CHEBI:29081 )

Ontology

Hypertension

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Plant

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	-0.45	HANSCH,C ET AL. (1995)
Experimental pKa	8.9
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 64.65%; H 7.84%; N 8.38%; O 19.14%	DFC
Melting Point	184.5 oC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Synephrine, 3 TMS, GC-MS Spectrum	splash10-014i-0900000000-e033087fd86dbd769b28	Spectrum
GC-MS	Synephrine, non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-e033087fd86dbd769b28	Spectrum
GC-MS	Synephrine, non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-c295e3a3035d15a699ee	Spectrum
GC-MS	Synephrine, non-derivatized, GC-MS Spectrum	splash10-014i-2790000000-3975fb57a4851efa17dd	Spectrum
GC-MS	Synephrine, non-derivatized, GC-MS Spectrum	splash10-014i-1890000000-ddb8778ef0aef4591f0d	Spectrum
Predicted GC-MS	Synephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-0b89ec1502bbf0bb1879	Spectrum
Predicted GC-MS	Synephrine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9150000000-b5f2dbddba7baed4d774	Spectrum
Predicted GC-MS	Synephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-0900000000-87218af459df32d035bb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-0900000000-dd62606af13291e0de32	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0900000000-279ae142a098a2d8cfbb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0900000000-35c196c82d47f666eb5b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9600000000-b52451ff9bd8a3887bba	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-0c3a8e5c03a6dfd08667	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9700000000-3f120631d0bab91d44b4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0k9l-3900000000-6c610eef126262adfcb6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0k9l-2900000000-5d02f910ae0ae85cd74f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-0e740a4914c01adc1331	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0f7c-3900000000-8999539f6d5a8d3758f0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-f4b3f4b27d9ca7224d4b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9500000000-4ba94de2c8f5e98a4e2f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-1900000000-4355e00e21057ebd01c9	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-0900000000-a8d55f47d1721c88e142	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxr-0900000000-eb318fdbbcefb5c0f42b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01c3-8900000000-750750ed3b7c777f8966	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-73b64b38d378f6d409bc	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-2900000000-a2fc7c196d4cb2205cd2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-b3081d3e77cf948c0bab	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-59284684d3d1f5845efb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0q29-1900000000-eccd6882ea86aed6f824	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-7900000000-2f829c6bfc720e526453	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-832cda2fe5651203ce37	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0avl-2900000000-6a789e30e9999b4391e7	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C04548

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

29081

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BZZ90-X:BZZ90-X

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Synephrine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Synephrine (FDB001397)

Structure for FDB001397 (Synephrine)