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Pseudoephedrine

PubChem CID: 7028

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Compound Synonyms PSEUDOEPHEDRINE, (+)-Pseudoephedrine, d-Pseudoephedrine, Isoephedrine, trans-Ephedrine, d-Isoephedrine, Psi-ephedrin, Psi-ephedrine, (+)-threo-Ephedrine, d-psi-Ephedrine, Sudafed, Pseudoefedrina, 90-82-4, L(+)-psi-Ephedrine, L-(+)-Pseudoephedrine, (+)-psi-Ephedrine, Pseudoephedrinum, (+)-(1S,2S)-Pseudoephedrine, Besan, Pseudoephedrine d-form, (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol, Neodurasina, Acunaso, Pseudoephedrine (D), (1S,2S)-(+)-Pseudoephedrine, (1S,2S)-Pseudoephedrine, d-psi-2-Methylamino-1-phenyl-1-propanol, Pseudoefedrina [INN-Spanish], Pseudoephedrinum [INN-Latin], psi-Ephedrine, (+)-, Isoephedrine, d-, Pseudoephedrine, (+)-, pseudophedrine sulphate, HSDB 3177, UNII-7CUC9DDI9F, 7CUC9DDI9F, alpha-(1-(Methylamino)ethyl)benzyl alcohol, EINECS 202-018-6, CHEBI:51209, Pseudoephedrine (INN), Pseudoephedrine, L-(+)-, DTXSID0023537, Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (S-(R*,R*))-, EC 202-018-6, (+) threo-2-(methylamino)-1-phenyl-1-propanol, Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alpha-S)-, Benzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, (.alpha.S)-, 1-(S),2-(R)-ERYTHRO-(+)-EPHEDRINE, PSEUDOEPHEDRINE [INN], Pseudoefedrina (INN-Spanish), Pseudoephedrinum (INN-Latin), Pseudoephedrine [INN:BAN], PSEUDOEPHEDRINE (MART.), PSEUDOEPHEDRINE [MART.], Pseudoephedrine Ephedrine, Neodurasina (TN), Acunaso (TN), Pseudoephedrine polistirex, BENZENEMETHANOL, .ALPHA.-((1S)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-, (I)-Ephedrin, ephedrine-(racemic), (+) pseudoephedrine, d-Pseudoephedrine base, Spectrum_000878, Spectrum2_001303, Spectrum3_001771, Spectrum4_001162, Spectrum5_000650, Lopac-E-3250, PSEUDOEPHEDRINE(D), (1S,2S) pseudoephedrine, (1S,2S)-2-methylamino-1-phenylpropan-1-ol, (1s, 2s) pseudoephedrine, (1S,2S)-2-methylamino-1-phenyl-propan-1-ol, SCHEMBL4368, 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], DTXCID003537, GTPL7286, BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (S-(R*,R*))-, PSEUDOEPHEDRINE [WHO-DD], KBio1_000451, KBio2_001358, KBio2_003926, KBio2_006494, KBio3_002762, (1s, 2s)-(+)-pseudoephedrine, R01BA02, NINDS_000451, Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alphaS)-, 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, C02765, D08449, Q263958, BRD-K84175871-003-02-2, EPHEDRINE HYDROCHLORIDE IMPURITY B [EP IMPURITY], (alphaS)-alpha-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL, (.ALPHA.S)-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL, 202-018-6
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 32.299
Hydrogen Bond Donor Count 2.0
Pfizer 3 75 Rule False
Scaffold Graph Level C1CCCCC1
Np Classifier Class Phenylalanine-derived alkaloids
Deep Smiles CN[C@H][C@H]cccccc6))))))O))C
Heavy Atom Count 12.0
Classyfire Class Benzene and substituted derivatives
Description Pseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single ingredient preparations, or more commonly in combination with antihistamines, paracetamol and/or ibuprofen. Consumers often refer to it by a product which contains pseudoephedrine, such as Sudafed, the trademark for a common brand of pseudoephedrine hydrochloride in North America, Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine. (Reynolds, 1989) (-)-(1R,2R)-Pseudoephedrine is not used clinically, since it is associated with greater central nervous system (CNS) stimulatory effects. (+)-(1S,2S)-Pseudoephedrine is a less-potent CNS stimulant, yet it retains its efficacy as a decongestant. -- Wikipedia, Pseudoephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its indirect action on the adrenergic receptor system. While it may have weak agonist activity at adrenergic receptors, the principal mechanism is to displace noradrenaline from storage vesicles in presynaptic neurons. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the aforementioned postsynaptic adrenergic receptors. -- Wikipedia, Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine (Reynolds, 1989). The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant.[citation needed] However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529), Treatment for urinary incontinence is an unlabeled use for these medications. Unlabeled use means doctors can use the medication to treat a condition other than that for which it was first approved by the U.S. Food and Drug Administration (FDA). These medications are approved by the FDA for the treatment of nasal congestion caused by colds or allergies. However it has also been succesful in treating stress incontinence by increasing the pressure (tension) exerted by the muscles of the bladder neck and the urethra, which helps retain the urine within the bladder, An alpha and beta adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists, Pseudoephedrine is a sympathomimetic amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single-ingredient preparations, or more commonly in combination with antihistamines, paracetamol and/or ibuprofen. It is often referred to by consumers as Sudafed, which is the trademark for a common brand of pseudoephedrine hydrochloride. -- Wikipedia, Pseudoephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its indirect action on the adrenergic receptor system. While it may have weak agonist activity at alpha and beta adrenergic receptors, the principal mechanism is to displace noradrenaline from storage vesicles in presynaptic neurons. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the aforementioned postsynaptic adrenergic receptors. [HMDB]
Scaffold Graph Node Level C1CCCCC1
Classyfire Subclass Phenylpropanes
Isotope Atom Count 0.0
Molecular Complexity 121.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 2.0
Enzyme Uniprot Id P08913, P07550
Uniprot Id P21397, P08913, P07550, P35348, P19838, Q99714, Q27686, P06280, P16473, P08659, P33261, P14618, P16050, P18054, P15917, O14924, P40225, P10635, P08684, P11712, O15296, n.a., Q92835, O15357
Iupac Name (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
Nih Violation False
Prediction Hob 1.0
Class Benzene and substituted derivatives
Veber Rule True
Classyfire Superclass Benzenoids
Target Id NPT163, NPT149, NPT501, NPT210, NPT213, NPT52, NPT792, NPT1119, NPT96, NPT110, NPT109, NPT212
Xlogp 0.9
Superclass Benzenoids
Is Pains False
Subclass Phenylpropanes
Gsk 4 400 Rule True
Molecular Formula C10H15NO
Scaffold Graph Node Bond Level c1ccccc1
Prediction Swissadme 1.0
Inchi Key KWGRBVOPPLSCSI-WCBMZHEXSA-N
Silicos It Class Soluble
Fcsp3 0.4
Logs -0.671
Rotatable Bond Count 3.0
State Solid
Logd 1.394
Synonyms (+)-(1S,2S)-Pseudoephedrine, (+)-Pseudoephedrine, (+)-psi-Ephedrine, (+)-threo-Ephedrine, (1S,2S)-(+)-Pseudoephedrine, (1S,2S)-Pseudoephedrine, 1-ephedrine, 2-(Methylamino)-1-phenyl-1-propanol, Besan, D-isoephedrine, D-pseudoephedrine, d-Pseudoephedrine base, d-psi-2-Methylamino-1-phenyl-1-propanol, D-psi-Ephedrine, Isoephedrine, L-(+)-Pseudoephedrine, L(+)-psi-Ephedrine, Novafed, Pseudoefedrina, Pseudoephedrine, Pseudoephedrine d-form, Pseudoephedrine Ephedrine, Pseudoephedrinum, Psi-ephedrin, Psi-ephedrine, Sudafed, trans-Ephedrine, (+) Threo-2-(methylamino)-1-phenyl-1-propanol, (+)-Psi-ephedrine, (+)-Threo-ephedrine, D-Isoephedrine, D-Pseudoephedrine, D-Psi-2-methylamino-1-phenyl-1-propanol, D-Psi-ephedrine, L(+)-Psi-ephedrine, Pseudoephedrine D-form, Neodurasina, Acunaso, 1-Ephedrine, D-Pseudoephedrine base, Pseudoephedrine ephedrine, Ephedrine threo isomer, Pseudoephedrine HCL, Threo isomer OF ephedrine, Pseudoephedrine hydrochloride, (+)-isoephedrine, (+)-pseudoephedrine, (+)pseudoephedrine, d-pseudoephedrine, ephedrine, pseudo, ephedrine, pseudo (+), pseudo-ephedrine, pseudoephedrine, pseudoephedrine (+), ψ-ephedrine
Substituent Name Phenylpropane, Benzyl alcohol, Aralkylamine, Secondary alcohol, 1,2-aminoalcohol, Secondary amine, Secondary aliphatic amine, Hydrocarbon derivative, Aromatic alcohol, Organooxygen compound, Organonitrogen compound, Amine, Alcohol, Aromatic homomonocyclic compound
Esol Class Very soluble
Functional Groups CNC, CO
Compound Name Pseudoephedrine
Kingdom Organic compounds
Prediction Hob Swissadme 1.0
Exact Mass 165.115
Formal Charge 0.0
Brenk Violation False
Monoisotopic Mass 165.115
Hydrogen Bond Acceptor Count 2.0
Molecular Weight 165.23
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 2.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic homomonocyclic compounds
Lipinski Rule Of 5 True
Esol -1.6223632000000001
Inchi InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
Smiles C[C@@H]([C@H](C1=CC=CC=C1)O)NC
Nring 1.0
Np Classifier Biosynthetic Pathway Alkaloids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Taxonomy Direct Parent Phenylpropanes
Np Classifier Superclass Pseudoalkaloids

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