Compound: phenylephrine
SMILES: Oc1cc(ccc1)[C@@H](O)CNC
InChIKey: SONNWYBIRXJNDC-VIFPVBQESA-N
Synonyms: phenylephrine, 59-42-7, Metasynephrine, m-Oxedrine, Mezaton, m-Sympatol, Metasympatol, Mesatone, m-Sympathol, m-Synephrine, Metaoxedrine, Metaoxedrin, Visadron, Mesaton, Isophrin, Fenilefrina, R(-)-Phenylephrine, Phenylephrinum, m-Methylaminoethanolphenol, (-)-phenylephrine, 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol, (R)-phenylephrine, R(-)-Mezaton, l-(3-Hydroxyphenyl)-N-methylethanolamine, Phenylephrine Minims, Meta-synephrine, (-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol, Phenylephrine, (r)-, l-1-(m-Hydroxyphenyl)-2-methylaminoethanol, CHEBI:8093, J8.601K, 1WS297W6MV, l-m-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol, AB-101 (PHENYLEPHRINE), l-alpha-Hydroxy-beta-methylamino-3-hydroxy-L-ethylbenzene, Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, (R)-, Benzyl alcohol, m-hydroxy-alpha-((methylamino)methyl)-, (-)-, DTXSID9023465, 3-((1R)-1-hydroxy-2-methylaminoethyl)phenol, 3-[(1R)-1-hydroxy-2-methylaminoethyl]phenol, 3-((1R)-1-hydroxy-2-(methylamino)ethyl)phenol, Tannate, Phenylephrine, (R)-3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol, RefChem:6127, DTXCID903465, C01CA06, mesatonum (for the hydrochloride), R01AA04, R01AB01, R01BA03, S01FB01, S01GA05, 200-424-8, L-Phenylephrine, Mesatonum, Isophrim, Ak-dilate, Cyclomydril, Alcon Efrin, Dionephrine, Adrianol, Isopto Frin, Prefrin Liquifilm, (R)-3-(1-hydroxy-2-(methylamino)ethyl)phenol, Duo-Medihaler, MFCD00044749, Phenylephrine (INN), (R)-(-)-phenylephrine, R-PHENYLEPHRINE, Ah-Chew, Spersaphrine, Dilatair, Doktors, Duration, Neofrin, Ocugestrin, Phenoptic, Fenilefrina [INN-Spanish], (alphar)-3-hydroxy-alpha-[(methylamino)methyl]benzenemethanol, Phenylephrinum [INN-Latin], Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-, (R)-, Ak-nefrin, I-Phrine, PHENYLEPHRINE [INN], Phenylephrine, l-, Nostril Spray Pump, Phenylephrine [INN:BAN], Minims Phenylephrine, Hemorid, Nostril Spray Pump Mild, Alconefrin Nasal Drops 12, Alconefrin Nasal Drops 25, Alconefrin Nasal Drops 50, Alconefrin Nasal Spray 25, Neo-Synephrine Nasal Drops, Neo-Synephrine Nasal Jelly, Neo-Synephrine Nasal Spray, Ocu-Phrin Sterile Eye Drops, (-)-m-Oxedrine, Relief Eye Drops for Red Eyes, HSDB 3383, EINECS 200-424-8, Phenylephrine Minims (TN), phenylene, UNII-1WS297W6MV, AI3-02402, CCRIS 8464, Phenylephrine; (1R)-1-(3-Hydroxyphenyl)-2-(methylamino)ethanol, Phenylephrine CRS, Mydfrin (Salt/Mix), Nostril (Salt/Mix), Prefrin (Salt/Mix), Adrianol (Salt/Mix), Neophryn (Salt/Mix), Biomydrin (Salt/Mix), R-(-)-Phenylephrine, Spectrum_001101, Ak-dilate (Salt/Mix), Ak-nefrin (Salt/Mix), Phenylephrine (Standard), Alcon efrin (Salt/Mix), Spectrum2_001280, Spectrum3_000770, Spectrum4_000967, Spectrum5_001411, Lopac-P-6126, PHENYLEPHRINE [MI], Epitope ID:613451, EC 200-424-8, SCHEMBL4711, CHEMBL1215, PHENYLEPHRINE [HSDB], Lopac0_000920, BSPBio_002420, GTPL485, KBioGR_001313, KBioSS_001581, PHENYLEPHRINE [VANDF], BIDD:GT0157, DivK1c_000597, PHENYLEPHRINE [MART.], SPBio_001280, Benzyl alcohol, m-hydroxy-.alpha.-((methylamino)methyl)-, (-)-, PHENYLEPHRINE [WHO-DD], (R)-2-Hydroxy-2-(3-hydroxyphenyl)-N-methylethylamine, component of Entex (Salt/Mix), orb1307589, component of Relief (Salt/Mix), SCHEMBL29382851, component of Comhist (Salt/Mix), component of Demazin (Salt/Mix), HY-B0769R, KBio1_000597, KBio2_001581, KBio2_004149, KBio2_006717, KBio3_001640, component of Vasosulf (Salt/Mix), component of Zincfrin (Salt/Mix), NINDS_000597, PHENYLEPHRINE [EP IMPURITY], AAA05942, component of Cerose dm (Salt/Mix), component of Prefrin-a (Salt/Mix), HY-B0769, component of Cyclomydril (Salt/Mix), PHENYLEPHRINE [EP MONOGRAPH], BDBM50067212, EBC-26121, Neo-Synephrine Pediatric Nasal Drops, PDSP1_001108, PDSP2_001092, component of Decongestant (Salt/Mix), component of Dristan cold (Salt/Mix), AKOS006282042, CCG-205002, CS-6187, DB00388, SDCCGSBI-0050895.P005, component of Histalet forte (Salt/Mix), component of Ru-tuss liquid (Salt/Mix), IDI1_000597, component of Ru-tuss tablets (Salt/Mix), NCGC00015825-01, NCGC00015825-02, NCGC00024257-03, NCGC00024257-05, NCGC00024257-06, NCGC00024257-07, NCGC00024257-19, (R)-(-)-Phenylephrine; L-Phenylephrine, AS-13635, SY102073, component of Hycomine compound (Salt/Mix), SBI-0050895.P004, component of Dristan nasal mist (Salt/Mix), NS00008779, P0395, C07441, D08365, EN300-160202, AB00053522_11, AB00053522_12, 3-[1-Hydroxy-2-(methylamino)ethyl]phenol, (R)-, AT-057/40243664, Q421910, (-)-1-(3-HYDROXYPHENYL)-2-METHYLAMINOETHANOL, BRD-K73381542-003-22-6, BRD-K73381542-003-23-4, BRD-K73381542-003-24-2, (-)-m-Hydroxy-.alpha.-(methylaminomethyl)benzyl alcohol, l-m-Hydroxy-.alpha.-((methylamino)methyl)benzyl alcohol, Z1198723489, (|_R)-3-Hydroxy-|_-[(methylamino)methyl]benzenemethanol, (R)-3-Hydroxy-.alpha.-[(methylamino)methyl]benzenemethanol, 3-[(1R)-1-Hydroxy-2-(methylamino)ethyl]phenol, AldrichCPR, l-.alpha.-Hydroxy-.beta.-methylamino-3-hydroxy-l-ethylbenzene, (-)-3 HYDROXY-.ALPHA.-((METHYLAMINO)METHYL)BENZENEMETHANOL, Benzenemethanol, 3-hydroxy-a-[(methylamino)methyl]-, (.alpha.R)-, 1228015-39-1
Theoretical properties:
molecular_formula: C9H13NO2
molecular_weight: 167.20 g/mol
exact_mass: 167.094628657 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 12
topological_polar_surface_area: 52.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 140-145 °C
solubility: Freely soluble in water
Descriptions:
{"pubchem": "Phenylephrine is a member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring. It has a role as a sympathomimetic agent, an alpha-adrenergic agonist, a cardiotonic drug, a protective agent, a mydriatic agent, a vasoconstrictor agent and a nasal decongestant. It is a member of phenylethanolamines, a member of phenols and a secondary amino compound. It is a conjugate base of a phenylephrine(1+).", "chebi": "A member of the class of the class of phenylethanolamines that is (1<i>R</i>)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.", "chembl": "PHENYLEPHRINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among others, is a medication used as a decongestant for uncomplicated nasal congestion in the form of a nasal spray or oral tablet, intravenously in cases of low blood pressure, or as a suppository to relieve hemorrhoids. It can also be applied to the skin.\nCommon side effects when taken by mouth or injected include nausea, vomiting, headache, and anxiety. Use on hemorrhoids is generally well tolerated. Severe side effects may include a slow heart rate, intestinal ischemia, chest pain, kidney failure, and tissue death at the site of injection. It is unclear whether its use during pregnancy and breastfeeding is safe. Phenylephrine is a selective \u03b11-adrenergic receptor agonist with minimal to no \u03b2-adrenergic receptor agonist activity or induction of norepinephrine release. It causes constriction of both arteries and veins.\nPhenylephrine was patented in 1933 and came into medical use in 1938. It is available as a generic medication. Unlike pseudoephedrine, abuse of phenylephrine is very uncommon. Its effectiveness as an oral nasal decongestant has been questioned. In 2023, a U.S. Food and Drug Administration (FDA) panel concluded that the drug was ineffective as a nasal decongestant when taken orally, performing no better than placebo. In November 2024, the FDA proposed to remove oral phenylephrine as an active ingredient that can be used in over-the-counter (OTC) monograph drug products for the temporary relief of nasal congestion."}