Showing Compound Phenylephrine (FDB022891)

Record Information

Version

1.0

Creation date

2011-09-21 00:21:12 UTC

Update date

2015-10-09 22:31:29 UTC

Primary ID

FDB022891

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phenylephrine

Description

Phenylephrine, also known as mesaton or m-sympathol, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. Phenylephrine is a very strong basic compound (based on its pKa). Phenylephrine is a bitter tasting compound.

CAS Number

59-42-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol	ChEBI
Fenilefrina	ChEBI
L-(3-Hydroxyphenyl)-N-methylethanolamine	ChEBI
Phenylephrinum	ChEBI
R(-)-Phenylephrine	ChEBI
Phenylephrine minims	Kegg
(-)-m-Hydroxy-a-(methylaminomethyl)benzyl alcohol	Generator
(-)-m-Hydroxy-α-(methylaminomethyl)benzyl alcohol	Generator
Adrianol	HMDB
Ak-dilate	HMDB
Ak-nefrin	HMDB
Alcon efrin	HMDB
Alconefrin nasal drops 12	HMDB
Alconefrin nasal drops 25	HMDB
Alconefrin nasal drops 50	HMDB
Alconefrin nasal spray 25	HMDB
Biomydrin	HMDB
Dilatair	HMDB
Dionephrine	HMDB
Doktors	HMDB
Duration	HMDB
I-phrine	HMDB
Isophrim	HMDB
Isophrin	HMDB
Isopto frin	HMDB
m-Methylaminoethanolphenol	HMDB
m-Oxedrine	HMDB
m-Sympathol	HMDB
m-Sympatol	HMDB
m-Synephrine	HMDB
Mesaton	HMDB
Mesatone	HMDB
Mesatonum	HMDB
Metaoxedrin	HMDB
Metaoxedrine	HMDB
Metaoxedrinum	HMDB
Metasympatol	HMDB
Metasynephrine	HMDB
Mezaton	HMDB
Minims phenylephrine	HMDB
Mydfrin	HMDB
Neo-synephrine	HMDB
Neo-synephrine nasal drops	HMDB
Neo-synephrine nasal jelly	HMDB
Neo-synephrine nasal spray	HMDB
Neo-synephrine pediatric nasal drops	HMDB
Neofrin	HMDB
Neophryn	HMDB
Neosynephrine	HMDB
Nostril	HMDB
Nostril spray pump	HMDB
Nostril spray pump mild	HMDB
Ocu-phrin sterile eye drops	HMDB
Ocu-phrin sterile ophthalmic solution	HMDB
Ocugestrin	HMDB
Phenoptic	HMDB
Prefrin	HMDB
Prefrin liquifilm	HMDB
Pyracort D	HMDB
R(-)-Mezaton	HMDB
Relief eye drops for red eyes	HMDB
Rhinall	HMDB
Spersaphrine	HMDB
Vicks sinex	HMDB
Visadron	HMDB
Neo synephrine	HMDB
Phenylephrine tannate	HMDB
Tannate, phenylephrine	HMDB
(R)-3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol	HMDB
Phenylephrine hydrochloride	HMDB
Ak-Dilate	hmdb
Ak-Nefrin	hmdb
Alconefrin Nasal Drops 12	hmdb
Alconefrin Nasal Drops 25	hmdb
Alconefrin Nasal Drops 50	hmdb
Alconefrin Nasal Spray 25	hmdb
I-Phrine	hmdb
Isopto Frin	hmdb
Minims Phenylephrine	hmdb
Neo-Synephrine	hmdb
Neo-Synephrine Nasal Drops	hmdb
Neo-Synephrine Nasal Jelly	hmdb
Neo-Synephrine Nasal Spray	hmdb
Neo-Synephrine Pediatric Nasal Drops	hmdb
Nostril Spray Pump	hmdb
Nostril Spray Pump Mild	hmdb
Ocu-Phrin Sterile Eye Drops	hmdb
Ocu-Phrin Sterile Ophthalmic Solution	hmdb
Prefrin Liquifilm	hmdb
Relief Eye Drops for Red Eyes	hmdb
Vicks Sinex	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	22 g/L	ALOGPS
logP	-0.69	ALOGPS
logP	-0.07	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Acidic)	9.07	ChemAxon
pKa (Strongest Basic)	9.69	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	18.2 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

3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol

InChI Identifier

InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1

InChI Key

SONNWYBIRXJNDC-VIFPVBQESA-N

Isomeric SMILES

CNC[C@H](O)C1=CC(O)=CC=C1

Average Molecular Weight

167.205

Monoisotopic Molecular Weight

167.094628665

Classification

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Aromatic alcohol
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethanolamines (CHEBI:8093 )
secondary amino compound (CHEBI:8093 )

Ontology

Nerve cell

Tissue and substructures:

Biofluid and excreta:

Organ and components:

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Phenylephrine, 2 TMS, GC-MS Spectrum	splash10-014i-0900000000-b11a2a880d1683fa6cae	Spectrum
GC-MS	Phenylephrine, 2 TMS, GC-MS Spectrum	splash10-01b9-6900000000-bbdd210a846be116dbcd	Spectrum
GC-MS	Phenylephrine, non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-b11a2a880d1683fa6cae	Spectrum
GC-MS	Phenylephrine, non-derivatized, GC-MS Spectrum	splash10-01b9-6900000000-bbdd210a846be116dbcd	Spectrum
Predicted GC-MS	Phenylephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-3ea7ffd258ffba5a376a	Spectrum
Predicted GC-MS	Phenylephrine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-4920000000-54a2b2a88914c83610f2	Spectrum
Predicted GC-MS	Phenylephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0udi-0900000000-d95a741ffcfe3f7bb7e9	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0006-9800000000-7695881b36499169fb71	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-054o-9200000000-888fce606d860cd39be2	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-edfcbc18ccdb6872b791	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-0900000000-15132688bbc7ac0be42f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-2900000000-34ccc7192518d4c14210	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-3900000000-e619f4210f81c11f61be	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00dl-6900000000-3178337a019ac9bf313d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0gb9-0900000000-e738818606836c1d6d1a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0udi-0900000000-36b72327f64f1355a502	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-052o-4900000000-935a9659fe39602b138d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-052f-9800000000-7d83555b537d6fec673b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-054o-9400000000-5ef2f6d1da57087e6ac7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-0900000000-4a910a2109ba191b96e7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-edfcbc18ccdb6872b791	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-15132688bbc7ac0be42f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-2900000000-34ccc7192518d4c14210	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-3900000000-e8a5a4f1aae0796866a7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00dl-6900000000-3178337a019ac9bf313d	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-0900000000-8c4893aa69ea6a1ceecb	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxr-0900000000-4406afb22d76646e2ef8	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01c3-7900000000-56a2a2741d2166bf31bc	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-0cf5a5fa80f87facb9ad	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-2900000000-687762e0d4bf3efbffec	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-140e96de62b4341791d9	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB00388

HMDB ID

HMDB02182

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

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

Phenylephrine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Alpha-2A adrenergic receptor	ADRA2A	P08913
Alpha-2B adrenergic receptor	ADRA2B	P18089

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Phenylephrine (FDB022891)

Structure for FDB022891 (Phenylephrine)