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90-82-4 molecular structure
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(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol

ChemBase ID: 730
Molecular Formular: C10H15NO
Molecular Mass: 165.2322
Monoisotopic Mass: 165.11536411
SMILES and InChIs

SMILES:
O[C@H]([C@@H](NC)C)c1ccccc1
Canonical SMILES:
CN[C@H]([C@H](c1ccccc1)O)C
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
InChIKey:
KWGRBVOPPLSCSI-WCBMZHEXSA-N

Cite this record

CBID:730 http://www.chembase.cn/molecule-730.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
IUPAC Traditional name
pseudoephedrine
Brand Name
Afrinol
Balminil Decongestant Syrup
Benylin Decongestant
Besan
Cenafed
D-Isoephedrine
D-Pseudoephedrine
Decofed
Dimetapp Decongestant
Dimetapp Decongestant Pediatric Drops
Drixoral N.D.
Drixoral Nasal Decongestant
Efidac 24 Pseudoephedrine Hcl
Efidac/24
Eltor 120
Genaphed
Isoephedrine
Maxenal
Myfedrine
Novafed
Pedia Care
Pseudo
Pseudo 60's
Pseudo-12
Pseudoefedrina [INN-Spanish]
Pseudoephedrine D-Form
Pseudoephedrine Ephedrine
Pseudoephedrine Hcl
Pseudoephedrinum [INN-Latin]
Psi-Ephedrin
Psi-Ephedrine
Robidrine
Sudafed
Sudafed 12 Hour
Sudafed Decongestant
Sudafed Decongestant 12 Hour
Sudafed Decongestant Extra Strength
Trans-Ephedrine
Triaminic AM Decongestant Formula
Triaminic Infant Oral Decongestant Drops
Afrin
Chlor-Trimeton
Synonyms
(+)-ψ-Ephedrine
(+)-Pseudoephedrine
(1S,2S)-2-Methylamino-1-phenyl-1-propanol
d-Isoephedrine
d-Pseudoephedrine
(1S,2S)-(+)-Pseudoephedrine
Pseudoephedrine
(+)-Pseudoephedrine
(+)-伪麻黄碱
(1S,2S)-(+)-伪麻黄碱
(+)-ψ-麻黄碱
(1S,2S)-2-甲氨基-1-苯基-1-丙醇
d-伪麻黄碱
d-异麻黄碱
(+)-伪麻黄碱
CAS Number
90-82-4
EC Number
202-018-6
MDL Number
MFCD00064256
Beilstein Number
2414132
PubChem SID
24887980
24857282
160964193
46508190
PubChem CID
7028

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.889531  H Acceptors
H Donor LogD (pH = 5.5) -1.8580045 
LogD (pH = 7.4) -0.7786886  Log P 1.3178347 
Molar Refractivity 49.6873 cm3 Polarizability 19.85273 Å3
Polar Surface Area 32.26 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.0  LOG S -1.3 
Solubility (Water) 8.26e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
7 mg/L expand Show data source
Melting Point
116-119 °C expand Show data source
118-120 °C expand Show data source
Optical Rotation
[α]20/D +52°, c = 0.6 in ethanol expand Show data source
[α]20/D +53±2°, c = 0.6% in ethanol expand Show data source
Hydrophobicity(logP)
1.4 expand Show data source
RTECS
UL5800000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22-36/37/38 expand Show data source
Safety Statements
26-37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H315-H319-H332-H335 expand Show data source
GHS Precautionary statements
P261-P280-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
≥96.0% (sum of enantiomers, GC) expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Empirical Formula (Hill Notation)
C10H15NO expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank - DB00852 external link
Item Information
Drug Groups approved
Description 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. [PubChem]
Indication For the treatment of nasal congestion, sinus congestion, Eustachian tube congestion, and vasomotor rhinitis, and as an adjunct to other agents in the optimum treatment of allergic rhinitis, croup, sinusitis, otitis media, and tracheobronchitis. Also used as first-line therapy of priapism.
Pharmacology Pseudoephedrine is a sympathomimetic agent, structurally similar to ephedrine, used to relieve nasal and sinus congestion and reduce air-travel-related otalgia in adults. 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 and/or paracetamol/ibuprofen. Unlike antihistamines, which modify the systemic histamine-mediated allergic response, pseudoephedrine only serves to relieve nasal congestion commonly associated with colds or allergies. The advantage of oral pseudoephedrine over topical nasal preparations, such as oxymetazoline, is that it does not cause rebound congestion (rhinitis medicamentosa).
Toxicity Common adverse reactions include nervousness, restlessness, and insomnia. Rare adverse reactions include difficult/painful urination, dizziness/lightheadedness, heart palpitations, headache, increased sweating, nausea/vomiting, trembling, troubled breathing, unusual paleness, and weakness.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption Pseudoephedrine is readily and almost completely absorbed from the GI tract and there is no evidence of first-pass metabolism.
Half Life 9-16 hours
Protein Binding Pseudoephedrine does not bind to human plasma proteins over the concentration range of 50 to 2000 ng/mL
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - E2625 external link
Biochem/physiol Actions
非选择性肾上腺素激动剂;减充血剂
Sigma Aldrich - 287636 external link
Biochem/physiol Actions
Non-selective adrenergic agonist; decongestant
Packaging
5, 25, 100 g in glass bottle
Sigma Aldrich - 82545 external link
Biochem/physiol Actions
Non-selective adrenergic agonist; decongestant
Other Notes
Sales restrictions may apply

REFERENCES

REFERENCES

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PATENTS

PATENTS

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