PSEUDOEPHEDRINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H15NO
Molecular Weight	165.2322
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN[C@@H](C)[C@@H](O)C1=CC=CC=C1

InChI

InChIKey=KWGRBVOPPLSCSI-WCBMZHEXSA-N

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

HIDE SMILES / InChI

Molecular Formula	C10H15NO
Molecular Weight	165.2322
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Pseudoephedrine is a sympathomimetic drug. Pseudoephedrine acts as an adrenomimetic and inhibitor of monoamine transporters. Ephedra sinica, a species of ephedra (ma huang), contains ephedrine and pseudoephedrine. Ephedra has been found to stimulate the nervous system, increase airflow into the lungs and constrict blood vessels. In combination with caffeine, ephedra appears to cause weight loss. Pseudoephedrine is a decongestant that shrinks blood vessels in the nasal passages. Pseudoephedrine is used to relieve nasal or sinus congestion caused by the common cold, sinusitis, and hay fever and other respiratory allergies.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine transporter 180	Inhibitor 8,297	5.6 µM [IC50]
Norepinephrine transporter 191	Inhibitor 8,297	1.18 µM [IC50]
Adrenergic receptor alpha 64	Agonist 2,678
Adrenergic receptor beta 87	Agonist 2,678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nasal congestion 26	Primary		Approved 8,429	SUDAFED 24 HOUR

C_max

Value	Dose	Co-administered	Analyte	Population
292 ng/mL	120 mg single, oral		PSEUDOEPHEDRINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
4346 ng × h/mL	120 mg single, oral		PSEUDOEPHEDRINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.3 h	120 mg single, oral		PSEUDOEPHEDRINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1500 mg single, oral Overdose	unknown, 16 years	Other AEs: Rhabdomyolysis, Creatine kinase increased...
150 mg 2 times / day multiple, oral Highest studied dose	healthy, 24 years	Other AEs: Tension, Dry mouth...
90 mg 1 times / day multiple, oral Overdose	unhealthy, 3 years	Disc. AE: Urinary retention...
30 mg 2 times / day multiple, oral	unhealthy, 37 years	Disc. AE: Ischemic colitis, Abdominal pain...
720 mg 1 times / day multiple, oral Highest studied dose	unhealthy, 38.8 years

Showing 1 to 5 of 9 entries

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AEs

Show entries

AE	Significance	Dose	Population
Blood myoglobin increased	1 patient	1500 mg single, oral Overdose	unknown, 16 years
Creatine kinase increased	1 patient	1500 mg single, oral Overdose	unknown, 16 years
Rhabdomyolysis	1 patient	1500 mg single, oral Overdose	unknown, 16 years
Palpitations	10 patients	150 mg 2 times / day multiple, oral Highest studied dose	healthy, 24 years
Restlessness	10 patients	150 mg 2 times / day multiple, oral Highest studied dose	healthy, 24 years

Showing 1 to 5 of 21 entries

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51209	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51209
eMolecules	494893	https://www.emolecules.com/cgi-bin/more?vid=494893
ZINC	ZINC000000020259	http://zinc15.docking.org/substances/ZINC000000020259

Showing 1 to 3 of 3 entries

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PubMed

Show entries

Title	Date	PubMed
Angle closure risk from proprietary medicines.	2001 Apr	11339612
Epinephrine analogues.	2001 Nov	12806441
Chloroephedrine: contaminant of methamphetamine synthesis with cardiovascular activity.	2001 Nov 1	11672944
Cathinone (Khat) and methcathinone (CAT) in urine specimens: a gas chromatographic-mass spectrometric detection procedure.	2001 Oct	11599595
Community pharmacists' experience of over-the-counter medicine misuse in Scotland.	2001 Sep	11688306

Showing 1 to 5 of 19 entries

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Patents

Sample Use Guides

In Vivo Use Guide

SUDAFED® 24 HOUR TABLET, EXTENDED RELEASE; ORAL (PSEUDOEPHEDRINE HYDROCHLORIDE) 240MG adults and children 12 years and older: a tablet with water every 24 hours children under 12 years: do not use this product in children under 12 years of age

Route of Administration: Oral

In Vitro Use Guide

Unknown