Compound: phenylpropanolamine
SMILES: O[C@H](c1ccccc1)[C@@H](N)C
InChIKey: DLNKOYKMWOXYQA-CBAPKCEASA-N
Synonyms: phenylpropanolamine, Norephedrine, Propadrine, Phenylpropanolaminum, Phenylfenesin, Rinexin, Fansia, Fenilpropanolamina, 14838-15-4, erythro-2-Amino-1-phenyl-1-propanol, 33RU150WUN, CHEBI:8104, NSC17704, Benzenemethanol, alpha-(1-aminoethyl)-, (R*,S*)-(+-)-, NSC-9920, RefChem:56356, Phenylpropanolamine 1534, R01BA01, 211-850-9, 238-900-2, 2-amino-1-phenylpropan-1-ol, NSC9920, (-)-Norephedrine, l-Norephedrine, (1R,2S)-Norephedrine, 492-41-1, (-)-Norephedrin, l-Phenylpropanolamine, (1R,2S)-(-)-Norephedrine, Mydriatin, (1R,2S)-2-amino-1-phenylpropan-1-ol, erythro-(1R,2S)-Norephedrine, USAF CS-6, NOREPHEDRINE, (-)-, (R,S)-(-)-Norephedrine, (-)-Phenylpropanolamine, (1R,2S)-2-Amino-1-phenyl-1-propanol, (+-)-Norephedrine, (+/-)-Norephedrine, (+-)-Phenylpropanolamine, NSC 17704, NSC-17704, dl-Phenylpropanolamine, Rhindecon, Mucron, 1-Propanol, 2-amino-1-phenyl-, (-)-, 57B9YG5Y1E, Norpseudoephedrine, (1R,2S)-PHENYLPROPANOLAMINE, (1R,2S)-(-)-Norephedrine, 99%, Benzyl alcohol,.alpha.-(1-aminoethyl)-, Phenylpropanolamine (INN), (+/-)-Phenylpropanolamine, dl-1-Phenyl-2-aminopropanol-1, PHENYLPROPANOLAMINE [INN], Benzenemethanol, .alpha.-((1S)-1-aminoethyl)-, (.alpha.R)-, Benzenemethanol, .alpha.-[(1S)-1-aminoethyl]-, (.alpha.R)-, Super Odrinex, dl-2-Amino-1-hydroxy-1-phenylpropane, Phenylpropanolamina, Fenilpropanolamina [Italian], (+-)-Norephedrin, SR-05000001534, EINECS 207-755-7, CHEMBL136560, Phenylpropanolamine (VAN), PPA [Nasal Decongestant], UNII-33RU150WUN, UNII-57B9YG5Y1E, 1-norephedrine, Phenylpropanolamine [INN:BAN], HSDB 6485, Phenylpropanolaminum [INN-Latin], Benzyl alcohol, alpha-(1-aminoethyl)-, (-)-, Phenylpropanolamina [INN-Spanish], NSC 9920, EINECS 211-850-9, EINECS 238-900-2, Fansia (TN), 1-(-)-ephedrine, dl-alpha-(1-Aminoethyl)benzyl alcohol, Benzyl alcohol, alpha-(1-aminoethyl)-, BRN 3196918, dl-alpha-Hydroxy-beta-aminopropylbenzene, Benzenemethanol, alpha-((1S)-1-aminoethyl)-, (alphaR)-, Benzenemethanol, alpha-(1-aminoethyl)-, (R-(R*,S*))-, Spectrum_001103, Spectrum2_000016, Spectrum3_000889, Spectrum4_000983, Spectrum5_001156, (1R,2S)- Norephedrine, Epitope ID:768756, Benzenemethanol, .alpha.-(1-aminoethyl)-, [R-(R*,S*)]-, WLN: ZY1&YQR -L, KBioGR_001385, KBioSS_001583, (R*,S*)-(1)-alpha-(1-Aminoethyl)benzyl alcohol, (R-(R*,S*))-alpha-(1-Aminoethyl)benzyl alcohol, 4-13-00-01875 (Beilstein Handbook Reference), SCHEMBL152038, (1s,2r)-2-hydroxy-2-phenyl-1-methyl-1-aminoethane, 1S,2R-PHENYLPROPANOLAMINE HYDROCHLORIDE, Benzenemethanol, alpha-(1-aminoethyl)-, (R*,S*)-, SPBio_000051, PHENYLPROPANOLAMINE, L-, SCHEMBL1403051, (1r, 2s)-(-)-norephedrine, PHENYLPROPANOLAMINE [MI], CHEBI:80680, KBio2_001583, KBio2_004151, KBio2_006719, KBio3_001778, DTXSID10889348, PHENYLPROPANOLAMINE [HSDB], 1-Propanol, 2-amino-1-phenyl-, (1R, 2S)-(-)- norephedrine, HMS2090P12, PHENYLPROPANOLAMINE [VANDF], PHENYLPROPANOLAMINE [MART.], PHENYLPROPANOLAMINE, (-)-, (1R,2S)-(-)-Phenylpropanolamine, PHENYLPROPANOLAMINE [WHO-DD], PDSP1_001349, PDSP2_001333, AKOS015891206, CCG-214826, DB00397, Selegiline EP Impurity C (Free Base), Selegiline Hydrochloride EP Impurity C, N0608, (1R,2S)-(-)-2-Amino-1-phenyl-1-propanol, C07911, D08368, AB01275538-01, SR-05000001534-1, SR-05000001534-2, (-)-ERYTHRO-2-AMINO-2-METHYL-1-PHENYLETHANOL, (R*,S*)-(+/-)-alpha-(1-Aminoethyl)benzenemethanol, Q26840801, SELEGILINE HYDROCHLORIDE IMPURITY C [EP IMPURITY], Benzenemethanol, alpha-((1R)-1-aminoethyl)-, (alphaS)-rel-, BENZENEMETHANOL, .ALPHA.-(1-AMINOETHYL)-, (R*,S*)-, (+/-)-, InChI=1/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s
Theoretical properties:
molecular_formula: C9H13NO
molecular_weight: 151.21 g/mol
exact_mass: 151.099714038 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 11
topological_polar_surface_area: 46.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White, crystalline powder
color: White, crystalline powder
odor: Slight aromatic odor
melting_point: 190-194 °C
solubility: Freely soluble
Descriptions:
{"pubchem": "(-)-norephedrine is an amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid. It has a role as a plant metabolite. It is a member of amphetamines and a phenethylamine alkaloid.", "chebi": "An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1<i>R</i>,2<i>S</i>-stereoisomer). It is a plant alkaloid.", "chembl": "(1R,2S)-PHENYLPROPANOLAMINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Phenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent used as a decongestant and appetite suppressant. It was once common in prescription and over-the-counter cough and cold preparations. The medication is taken orally.\nSide effects of phenylpropanolamine include increased heart rate and blood pressure. Rarely, PPA has been associated with hemorrhagic stroke. PPA acts as a norepinephrine releasing agent, indirectly activating adrenergic receptors. As such, it is an indirectly acting sympathomimetic. It was once thought to act as a sympathomimetic with additional direct agonist action on adrenergic receptors, but this proved wrong. Chemically, phenylpropanolamine is a substituted amphetamine and is closely related to ephedrine, pseudoephedrine, amphetamine, and cathinone. It is usually a racemic mixture of the (1R,2S)- and (1S,2R)-enantiomers of \u03b2-hydroxyamphetamine and is also known as dl-norephedrine.\nPhenylpropanolamine was first synthesized around 1910 and its effects on blood pressure were characterized around 1930. It was introduced as medicine by the 1930s. It was withdrawn from many markets starting in 2000 after learning that it was associated with increased risk of hemorrhagic stroke. It was previously available both over-the-counter and by prescription. Phenylpropanolamine is available for both human and/or veterinary use in some countries."}