Compound: PSEUDOEPHEDRINE
SMILES: O[C@@H](c1ccccc1)[C@@H](NC)C
InChIKey: KWGRBVOPPLSCSI-WCBMZHEXSA-N
Synonyms: PSEUDOEPHEDRINE, d-Pseudoephedrine, Isoephedrine, trans-Ephedrine, d-Isoephedrine, Psi-ephedrin, Psi-ephedrine, (+)-threo-Ephedrine, d-psi-Ephedrine, Pseudoefedrina, 90-82-4, L(+)-psi-Ephedrine, L-(+)-Pseudoephedrine, (+)-psi-Ephedrine, Pseudoephedrinum, (+)-(1S,2S)-Pseudoephedrine, (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol, Neodurasina, Acunaso, (1S,2S)-(+)-Pseudoephedrine, d-psi-2-Methylamino-1-phenyl-1-propanol, psi-Ephedrine, (+)-, Isoephedrine, d-, Pseudoephedrine, (+)-, 7CUC9DDI9F, alpha-(1-(Methylamino)ethyl)benzyl alcohol, DTXSID0023537, CHEBI:51209, Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (S-(R*,R*))-, (+) threo-2-(methylamino)-1-phenyl-1-propanol, Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alpha-S)-, Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alphaS)-, Ephedrine Threo, Pseudoephedrine D-, RefChem:6179, Threo Isomer of Ephedrine, DTXCID003537, R01BA02, (1S,2S)-2-methylamino-1-phenyl-propan-1-ol, 202-018-6, (+)-Pseudoephedrine, Sudafed, Besan, Pseudoephedrine d-form, Pseudoephedrine (INN), Pseudoephedrine, L-(+)-, Pseudoephedrine (D), Benzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, (.alpha.S)-, Pseudoefedrina [INN-Spanish], Pseudoephedrinum [INN-Latin], PSEUDOEPHEDRINE [INN], Pseudoephedrine [INN:BAN], Pseudoephedrine Ephedrine, Neodurasina (TN), (+)-Pseudoephedrine hydrochloride, Acunaso (TN), pseudophedrine sulphate, HSDB 3177, EINECS 202-018-6, UNII-7CUC9DDI9F, dl-pseudoephedrine, BENZENEMETHANOL, .ALPHA.-((1S)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-, (I)-Ephedrin, ephedrine-(racemic), (+) pseudoephedrine, Pseudoephedrine, DL-, d-Pseudoephedrine base, Spectrum_000878, (+/-)-psi-Ephedrine, Spectrum2_001303, Spectrum3_001771, Spectrum4_001162, Spectrum5_000650, Lopac-E-3250, (1S,2S) pseudoephedrine, (1S,2S)-2-methylamino-1-phenylpropan-1-ol, (1s, 2s) pseudoephedrine, EC 202-018-6, SCHEMBL4368, Pseudoephedrine, (+/-)-, CHEMBL1590, PSEUDOEPHEDRINE [MI], (1S,2S)-2-(methylamino)-1-phenyl-propan-1-ol, BSPBio_003261, KBioGR_001763, KBioSS_001358, BIDD:GT0817, DivK1c_000451, PSEUDOEPHEDRINE [HSDB], SPBio_001365, PSEUDOEPHEDRINE [VANDF], 28S9JBG39X, GTPL7286, PSEUDOEPHEDRINE [MART.], BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (S-(R*,R*))-, PSEUDOEPHEDRINE [WHO-DD], KBio1_000451, KBio2_001358, KBio2_003926, KBio2_006494, KBio3_002762, (1s, 2s)-(+)-pseudoephedrine, NINDS_000451, PDSP1_001347, AKOS025401512, DB00852, IDI1_000451, (1S,2S)-(+)-Pseudoephedrine, 98%, NCGC00015408-01, NCGC00178180-01, NCI60_002955, SBI-0051498.P003, (+)-Pseudoephedrine, 1mg/ml in Acetonitrile, NS00067939, 1-(S),2-(R)-ERYTHRO-(+)-EPHEDRINE, C02765, D08449, Q263958, BRD-K84175871-003-02-2, EPHEDRINE HYDROCHLORIDE IMPURITY B [EP IMPURITY], rel-(alphaR)-alpha-[(1R)-1-(Methylamino)ethyl]benzenemethanol, (.ALPHA.S)-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL, Benzenemethanol, alpha-[(1R)-1-(methylamino)ethyl]-, (alphaR)-rel-, 4125-58-0
Theoretical properties:
molecular_formula: C10H15NO
molecular_weight: 165.23 g/mol
exact_mass: 165.115364102 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 12
topological_polar_surface_area: 32.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from ether
color: Crystals from ether
solubility: Sparingly sol in water; freely sol in alc or ether
Descriptions:
{"pubchem": "Pseudoephedrine is a member of the class of the class of phenylethanolamines that is (1S)-2-(methylamino)-1-phenylethan-1-ol in which the pro-S hydrogen at position 2 is replaced by a methyl group. It has a role as a central nervous system drug, a bronchodilator agent, a sympathomimetic agent, a xenobiotic, an anti-asthmatic drug, a vasoconstrictor agent, a plant metabolite and a nasal decongestant. It is a member of phenylethanolamines, a secondary alcohol and a secondary amino compound. It is a conjugate base of a pseudoephedrine(1+).", "chebi": "A member of the class of the class of phenylethanolamines that is (1<i>S</i>)-2-(methylamino)-1-phenylethan-1-ol in which the <em>pro</em>-<i>S</i> hydrogen at position 2 is replaced by a methyl group.", "chembl": "PSEUDOEPHEDRINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Pseudoephedrine, sold under the brand name Sudafed among others, is a sympathomimetic medication which is used as a decongestant to treat nasal congestion. It has also been used off-label for certain other indications, like treatment of low blood pressure. At higher doses, it may produce various additional effects including stimulant, appetite suppressant, and performance-enhancing effects. In relation to this, non-medical use of pseudoephedrine has been encountered. The medication is taken by mouth.\nSide effects of pseudoephedrine include insomnia, elevated heart rate, increased blood pressure, restlessness, dizziness, anxiety, and dry mouth, among others. Rarely, pseudoephedrine has been associated with serious cardiovascular complications like heart attack and hemorrhagic stroke. Some people may be more sensitive to its cardiovascular effects. Pseudoephedrine acts as a norepinephrine releasing agent, thereby indirectly activating adrenergic receptors. As such, it is an indirectly acting sympathomimetic. Pseudoephedrine significantly crosses into the brain, but has some peripheral selectivity due to its hydrophilicity. Chemically, pseudoephedrine is a substituted amphetamine and is closely related to ephedrine, phenylpropanolamine, and amphetamine. It is the (1S,2S)-enantiomer of \u03b2-hydroxy-N-methylamphetamine.\nAlong with ephedrine, pseudoephedrine occurs naturally in ephedra, which has been used for thousands of years in traditional Chinese medicine. It was first isolated from ephedra in 1889. Subsequent to its synthesis in the 1920s, pseudoephedrine was introduced for medical use as a decongestant. Pseudoephedrine is widely available over-the-counter (OTC) in both single-drug and combination preparations. Availability of pseudoephedrine has been restricted starting in 2005 as it can be used to synthesize methamphetamine. Phenylephrine has replaced pseudoephedrine in many over-the-counter oral decongestant products. However, oral phenylephrine appears to be ineffective as a decongestant. In 2023, pseudoephedrine was the 292nd most commonly prescribed medication in the United States, with more than 400,000 prescriptions. In 2023, the combination with brompheniramine and dextromethorphan was the 281st most commonly prescribed medication in the United States, with more than 700,000 prescriptions. In 2023, the combination with loratadine was the 300th most commonly prescribed medication in the United States, with more than 400,000 prescriptions."}