ContaminantDB: Ephedrine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:47 UTC

Update Date

2026-03-26 18:29:53 UTC

Accession Number

CHEM002392

Identification

Common Name

Ephedrine

Class

Small Molecule

Description

Ephedrine is only found in individuals who have consumed this drug. Ephedrine is 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] Ephedrine is similar in molecular structure to the well-known drugs phenylpropanolamine and methamphetamine, as well as to the important neurotransmitter epinephrine (adrenalin). Chemically, it is an alkaloid with a phenethylamine skeleton found in various plants in the genus Ephedra (family Ephedraceae). It works mainly by increasing the activity of norepinephrine (noradrenalin) on adrenergic receptors. It is most usually marketed as the hydrochloride or sulfate salt.

Contaminant Sources

DEA Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins

Contaminant Type

Adrenergic Agent
Amine
Central Nervous System Stimulant
Drug
Metabolite
Organic Compound
Sympathomimetic
Synthetic Compound
Vasoconstrictor Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,2S)-1-Phenyl-1-hydroxy-2-methylaminopropane	ChEBI
L(-)-Ephedrine	ChEBI
L-Ephedrine	ChEBI
L-Erythro-2-(methylamino)-1-phenylpropan-1-ol	ChEBI
(-)-Ephedrine	Kegg
Erythro isomer OF ephedrine	HMDB
Renaudin brand OF ephedrine hydrochloride	HMDB
Renaudin, ephedrine	HMDB
Ephedrine renaudin	HMDB
Sal-phedrine	HMDB
Sulfate, ephedrine	HMDB
Ephedrine hydrochloride	HMDB
Ephedrine sulfate	HMDB
Sal phedrine	HMDB
SalPhedrine	HMDB
Ephedrine erythro isomer	HMDB
Hydrochloride, ephedrine	HMDB
Wendt brand OF ephedrine sulfate	HMDB
Ephedrine	ChEBI

Chemical Formula

C₁₀H₁₅NO

Average Molecular Mass

165.232 g/mol

Monoisotopic Mass

165.115 g/mol

CAS Registry Number

299-42-3

IUPAC Name

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

Traditional Name

ephedrine

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-WPRPVWTQSA-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

phenylethanolamines (CHEBI:15407 )
phenethylamine alkaloid (CHEBI:15407 )
Alkaloids (C01575 )
Phenylalanine derived alkaloids (C01575 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

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	34°C
Boiling Point	255°C
Solubility	6.36E+004 mg/L (at 30°C)

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	18.8 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-9300000000-5bdf33e08e94f0c0bd26	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05di-9610000000-8f364065f58e7dd69444	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-33d551e262321705ae8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014j-0900000000-32a84e7b7e5332fe2026	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-82640acc94773485568a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-bdfb6079227a418eb706	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-c04df5fb623578be67ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00l2-1900000000-3a68bc210684b52a9fd8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0159-2900000000-e12bf9df640426404f1c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014j-0900000000-0218a677989aab76b176	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-3dd538034653edb47df1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-553c930e0970a8c1a866	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-0499cdf7955d013fca29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-015a-1900000000-f6b6229ef8c2d7fd24ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0159-2900000000-7c8549f8cd727886d67d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-bcbf5073df33d11415cc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0002-0900000000-8df1676350e720b21d8c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-015a-1900000000-8d8e8c6689866070b7de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0159-2900000000-573a202622c26aee5f4e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-0900000000-a2c5df7e718fb237fcb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-0900000000-33d551e262321705ae8a	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
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-bcc578719d003732d7f8	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
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral ; parenteral (intramuscular or intravenous injection). 85%.

Mechanism of Toxicity

Ephedrine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Metabolism

Route of Elimination: mainly renal Half Life: 3-6 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Ephedrine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia.

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Symptoms

Side-effects can include sweating, dry mouth, blurred vision, insomnia, loss of appetite, and dizziness. In addition users can feel restless, anxious and moody, become excitable and have a false sense of power and security. Amphetamine overdose can also cause cardiac arrhythmias, headaches, convulsions, hypertension, rapid heart rate, coma and death. Amphetamines are psychologically and physically addictive.

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

DB01364

HMDB ID

HMDB0015451

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID