Basic information
- Standard SMILES
CNCC(O)c1ccc(O)cc1- InChIKey
YRCWQPVGYLYSOX-UHFFFAOYSA-N- Molecular formula
- C9H13NO2
- Average molar mass
- 167.2 g/mol
- Monoisotopic mass
- 167.09462866
Overview
Synephrine is a phenethylamine alkaloid that is 4-(2-aminoethyl)phenol substituted by a hydroxy group at position 1 and a methyl group at the amino nitrogen. It has a role as an alpha-adrenergic agonist and a plant metabolite. It is a member of ethanolamines, a member of phenols and a phenethylamine alkaloid. It is a conjugate base of a synephrinium.
Names & identifiers
- Preferred name
- Synephrine
- IUPAC
- 4-[1-hydroxy-2-(methylamino)ethyl]phenol
Names & synonyms
SynephrineOxedrine94-07-5p-SynephrineParasympatolAnaleptinSimpalonSympatolSynthenateSympatholEthapheneDL-SYNEPHRINE
Show more names
4-[1-Hydroxy-2-(methylamino)ethyl]phenol4-(1-Hydroxy-2-(methylamino)ethyl)phenolAdvantra z1-(4-Hydroxyphenyl)-2-methylaminoethanolDTXSID0030588NSC-166285NSC-170956PEG5DP7434
Database identifiers
- CAS
94-07-5- PubChem CID
- 7172
- DTXSID
DTXSID0030588- ChEMBL
CHEMBL33720- ChEBI
CHEBI:29081- UNII
- PEG5DP7434
- EC Number
- 202-300-9
- Nikkaji
- J8.617G
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 52.5 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 122
Experimental & physicochemical properties
LogP
-0.45
-0.45
Physical DescriptionSolid
Dissociation Constants9.6
Collision Cross Section
241.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0030588]
130.49 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
132 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
134.4 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationSynephrine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Irrit. 2 (97.8%)
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
S - Sensory organs
QC - Cardiovascular system
QS - Sensory organs
QS - Sensory organs
MeSH Pharmacological Classification
Drugs that selectively bind to and activate alpha adrenergic receptors.
Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Drugs used to cause constriction of the blood vessels.
Drugs designed to treat inflammation of the nasal passages, generally the result of an infection (more often than not the common cold) or an allergy related condition, e.g., hay fever. The inflammation involves swelling of the mucous membrane that lines the nasal passages and results in inordinate mucus production. The primary class of nasal decongestants are vasoconstrictor agents. (From PharmAssist, The Family Guide to Health and Medicine, 1993)
Related reactions
9 records
Linked notes
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