ContaminantDB: Pseudoephedrine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2014-08-30 21:03:50 UTC

Update Date

2016-10-28 10:00:48 UTC

Accession Number

CHEM003515

Identification

Common Name

Pseudoephedrine

Class

Small Molecule

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]

Contaminant Sources

DEA Chemicals
FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Drug
Food Toxin
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+) Threo-2-(methylamino)-1-phenyl-1-propanol	ChEBI
(+)-(1S,2S)-Pseudoephedrine	ChEBI
(+)-Pseudoephedrine	ChEBI
(+)-Psi-ephedrine	ChEBI
(+)-Threo-ephedrine	ChEBI
(1S,2S)-(+)-Pseudoephedrine	ChEBI
(1S,2S)-Pseudoephedrine	ChEBI
2-(Methylamino)-1-phenyl-1-propanol	ChEBI
D-Isoephedrine	ChEBI
D-Pseudoephedrine	ChEBI
D-Psi-2-methylamino-1-phenyl-1-propanol	ChEBI
D-Psi-ephedrine	ChEBI
Isoephedrine	ChEBI
L(+)-Psi-ephedrine	ChEBI
L-(+)-Pseudoephedrine	ChEBI
Pseudoefedrina	ChEBI
Pseudoephedrine D-form	ChEBI
Pseudoephedrinum	ChEBI
Psi-ephedrin	ChEBI
Psi-ephedrine	ChEBI
trans-Ephedrine	ChEBI
Neodurasina	Kegg
Acunaso	Kegg
1-Ephedrine	HMDB
Besan	HMDB
D-Pseudoephedrine base	HMDB
Novafed	HMDB
Pseudoephedrine ephedrine	HMDB
Sudafed	HMDB
Ephedrine threo isomer	HMDB
Pseudoephedrine HCL	HMDB
Threo isomer OF ephedrine	HMDB
Pseudoephedrine hydrochloride	HMDB

Chemical Formula

C₁₀H₁₅NO

Average Molecular Mass

165.232 g/mol

Monoisotopic Mass

165.115 g/mol

CAS Registry Number

90-82-4

IUPAC Name

(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol

Traditional Name

pseudoephedrine

SMILES

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

InChI Identifier

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

InChI Key

KWGRBVOPPLSCSI-WCBMZHEXSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Alcohol
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic alcohol
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:51209 )
secondary amine (CHEBI:51209 )
Phenylalanine derived alkaloids (C02765 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

sympathomimetic agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	119 °C
Boiling Point	Not Available
Solubility	7 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	8.26 g/L	ALOGPS
logP	1	ALOGPS
logP	1.32	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.69 m³·mol⁻¹	ChemAxon
Polarizability	18.83 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-0c3fe6959703a851b9cc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05cr-4900000000-d9ac11e33b32a9e427ad	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-016s-3900000000-868bf4bba93d8b4be696	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0159-2900000000-6c55fc67b7576cb42a8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0006-9700000000-459686cbaf7d3b59c202	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0900000000-677d622716b4c2545f16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-2900000000-416def0e527ddf116a39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9500000000-155625a572f19610e138	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ea7e1b550b5dc0d6d41d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-2900000000-f4de25860574bb60daf1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9600000000-62e375458e5f83795e90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0297-3900000000-4496fbcd8548f7ccc58a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900000000-03e637debccd8d202e3c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-7ead088c2f003219a1cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-0282f3e8fc4bf9296a38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-3900000000-8ee8987e88c6a5601ef7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-e3932e53d7936649b8db	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-8f0484f72b48017f1f2e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Pseudoephedrine is readily and almost completely absorbed from the GI tract and there is no evidence of first-pass metabolism.

Mechanism of Toxicity

Pseudoephedrine acts directly on both alpha- and, to a lesser degree, beta-adrenergic receptors. Through direct action on alpha-adrenergic receptors in the mucosa of the respiratory tract, pseudoephedrine produces vasoconstriction. Pseudoephedrine relaxes bronchial smooth muscle by stimulating beta2-adrenergic receptors. Like ephedrine, pseudoephedrine releasing norepinephrine from its storage sites, an indirect effect. This is its main and direct mechanism of action. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the postsynaptic adrenergic receptors.

Metabolism

Hepatic. Half Life: 9-16 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

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.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00852

HMDB ID

HMDB0001943

FooDB ID

FDB022758

Phenol Explorer ID