Identification

Name
Ephedrine
Accession Number
DB01364
Type
Small Molecule
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.

Structure
Thumb
Synonyms
  • (-)-Ephedrine
  • (1R,2S)-1-Phenyl-1-hydroxy-2-methylaminopropane
  • L-Ephedrine
  • L-erythro-2-(Methylamino)-1-phenylpropan-1-ol
  • L(−)-ephedrine
External IDs
NSC-170951 / NSC-8971
Product Ingredients
IngredientUNIICASInChI Key
Ephedrine hydrochlorideNLJ6390P1Z50-98-6BALXUFOVQVENIU-GNAZCLTHSA-N
Ephedrine sulfateU6X61U5ZEG134-72-5CAVQBDOACNULDN-KHFUBBAMSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AkovazInjection50 mg/mLIntravenousAvadel Legacy Pharmaceuticals, Llc2016-08-01Not applicableUs
CorphedraInjection, solution50 mg/mLIntravenousPar Pharmaceutical2017-02-16Not applicableUs
Ephedrine SulfateInjection50 mg/mLIntravenousAkorn2017-03-01Not applicableUs
Ephedrine SulfateInjection, solution50 mg/mLIntravenousPar Pharmaceutical2017-02-16Not applicableUs
Ephedrine SulfateInjection50 mg/mLIntravenousAkorn2017-03-01Not applicableUs
Ephedrine Sulfate InjectionSolution50 mgIntramuscular; SubcutaneousHospira, Inc.1966-12-31Not applicableCanada
Ephedrine Sulfate Injection USPLiquid50 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated1990-12-31Not applicableCanada
Ephedrine Sulfate Injection USP, 50mg/mlLiquid50 mgIntramuscular; Intravenous; SubcutaneousAlveda Pharmaceuticals IncNot applicableNot applicableCanada
Ephedrine Sulphate Injection, USPSolution50 mgIntramuscular; Intravenous; SubcutaneousMylan Pharmaceuticals2002-07-292015-11-03Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ephedrine SulfateInjection50 mg/mLIntravenousSandoz2017-10-01Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ephedrine HClTablet8 mgOralKaizen Inc.2004-01-012010-02-26Canada
Ephedrine HClCapsule25 mgOralKaizen Inc.1997-04-221999-03-15Canada
Ephedrine HClTablet8 mgOralAdded Dimensions2002-04-302006-09-25Canada
Ephedrine HCl - Tab 25mgTablet25 mgOralAdded Dimensions1996-07-302002-02-25Canada
Ephedrine HCl 8 mgTablet8 mgOralNutrition Zone Products Inc.2002-09-202008-07-27Canada
Ephedrine Hydrochloride Tablets 25mgTablet25 mgOralProdemdis Enr.1998-05-042002-08-30Canada
Ephedrine SulfateCapsule25 mg/1OralWest Ward Pharmaceutical1993-09-01Not applicableUs
Ephedrine Tab 15mgTablet15 mgOralGlaxo Canada Inc1991-12-311996-09-10Canada
Ephedrine Tab 30mgTablet30 mgOralGlaxo Canada Inc1991-12-311996-09-10Canada
Formula C34 Tab .13mgTablet.13 mgOralHerbages Naturbec LtÉe.1979-12-312008-07-04Canada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EphedrineInjection, solution50 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2005-09-082016-02-19Us
EphedrineInjection, solution10 mg/mLIntravenousCantrell Drug Company2016-03-18Not applicableUs
Ephedrine SulfateInjection50 mg/mLIntramuscular; Intravenous; SubcutaneousAkorn2012-03-112017-06-20Us
Ephedrine SulfateInjection, solution50 mg/mLIntravenousNexus Pharmaceuticals Inc2015-06-08Not applicableUs
Ephedrine SulfateInjection50 mg/mLIntramuscular; Intravenous; SubcutaneousCardinal Health2009-04-012016-02-29Us
Ephedrine SulfateInjection, solution50 mg/mLIntramuscular; Intravenous; SubcutaneousSandoz2004-03-262017-09-30Us
Ephedrine SulfateInjection50 mg/mLIntramuscular; Intravenous; SubcutaneousAkorn2009-04-01Not applicableUs
Ephedrine SulfateInjection, solution50 mg/mLIntramuscular; Intravenous; SubcutaneousAndersen Pharma Llc2014-11-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Balminil Nasal OintmentEphedrine hydrochloride (6 mg) + Camphor (4 mg) + Chlorobutanol (2 mg) + Eucalyptol (6 mg) + Menthol (4 mg)OintmentNasalRougier Pharma Division Of Ratiopharm Inc1995-12-312003-09-22Canada
Bronch EzeEphedrine hydrochloride (4 mg) + Ammonium chloride (100 mg)SyrupOralPharmavite Laboratories (1987) Inc.1984-12-312000-08-18Canada
Bronchial Asthma ReliefEphedrine hydrochloride (12.5 mg/1) + Guaifenesin (200 mg/1)TabletOralWalgreens2002-02-13Not applicableUs
Broncho DilateEphedrine hydrochloride (12.5 mg/1) + Guaifenesin (200 mg/1)TabletOralContract Pharmacal Corporation2002-02-13Not applicableUs
Bronkaid Dual Action FormulaEphedrine sulfate (25 mg/1) + Guaifenesin (400 mg/1)Tablet, coatedOralBayer2006-01-01Not applicableUs
Bronkaid Dual Action FormulaEphedrine sulfate (25 mg/1) + Guaifenesin (400 mg/1)Tablet, coatedOralFoundation Consumer Healthcare2006-01-01Not applicableUs
Dymetadrine 25 - TabEphedrine hydrochloride (25 mg) + Guaifenesin (200 mg)TabletOralAdded Dimensions1996-12-232002-02-25Canada
Ephed AsthmaEphedrine hydrochloride (25 mg/1) + Guaifenesin (200 mg/1)TabletOralDickey Consumer Products DBA DMD2011-12-13Not applicableUs
Ephedrine V With GuaifenesinEphedrine hydrochloride (8 mg) + Guaifenesin (100 mg)TabletOralPumpuii Canada Inc.2003-03-152013-04-25Canada
GrippalinEphedrine hydrochloride (8 mg) + Acetaminophen (325 mg)TabletOralDistributions Multi Pro Inc.2000-09-132006-06-28Canada
Categories
UNII
GN83C131XS
CAS number
299-42-3
Weight
Average: 165.2322
Monoisotopic: 165.115364107
Chemical Formula
C10H15NO
InChI Key
KWGRBVOPPLSCSI-WPRPVWTQSA-N
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
IUPAC Name
(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
SMILES
CN[[email protected]@H](C)[[email protected]](O)C1=CC=CC=C1

Pharmacology

Indication

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

Structured Indications
Pharmacodynamics

Ephedrine is similar in structure to the derivatives amphetamine and methamphetamine. Chemically, it is an alkaloid derived from various plants in the genus Ephedra (family Ephedraceae). It works mainly by increasing the activity of noradrenaline on adrenergic receptors.

Mechanism of action

Ephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its direct and indirect actions on the adrenergic receptor system, which is part of the sympathetic nervous system. Ephedrine increases post-synaptic noradrenergic receptor activity by (weakly) directly activating post-synaptic α-receptors and β-receptors, but the bulk of its effect comes from the pre-synaptic neuron being unable to distinguish between real adrenaline or noradrenaline from ephedrine. The ephedrine, mixed with noradrenaline, is transported through the noradrenaline reuptake complex and packaged (along with real noradrenaline) into vesicles that reside at the terminal button of a nerve cell. Ephedrine's action as an agonist at most major noradrenaline receptors and its ability to increase the release of both dopamine and to a lesser extent, serotonin by the same mechanism is presumed to have a major role in its mechanism of action.

TargetActionsOrganism
USodium-dependent noradrenaline transporter
inverse agonist
Human
UAlpha-1A adrenergic receptorNot AvailableHuman
USynaptic vesicular amine transporter
inhibitor
Human
UAcetylcholinesteraseNot AvailableHuman
Absorption

85%

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

mainly renal

Half life

3-6 hours

Clearance
Not Available
Toxicity

Cardiovascular: tachycardia, cardiac arrhythmias, angina pectoris, vasoconstriction with hypertension

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Ephedrine.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Ephedrine.Approved, Investigational
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Ephedrine.Approved, Illicit
AtomoxetineAtomoxetine may increase the hypertensive activities of Ephedrine.Approved
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Ephedrine.Approved, Illicit
Benzylpenicilloyl PolylysineEphedrine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Ephedrine.Approved, Investigational
BucindololThe risk or severity of adverse effects can be increased when Ephedrine is combined with Bucindolol.Investigational
BunazosinBunazosin may decrease the vasoconstricting activities of Ephedrine.Investigational
CabergolineCabergoline may increase the hypertensive activities of Ephedrine.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Ephedrine.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Ephedrine is combined with Celiprolol.Approved, Investigational
ChlorphentermineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Chlorphentermine.Illicit, Withdrawn
ClenbuterolThe risk or severity of adverse effects can be increased when Ephedrine is combined with Clenbuterol.Approved, Vet Approved
DesfluraneEphedrine may increase the arrhythmogenic activities of Desflurane.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Ephedrine.Approved
Diethyl etherEphedrine may increase the arrhythmogenic activities of Diethyl ether.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Ephedrine.Approved
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Ephedrine.Approved
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Ephedrine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Ephedrine.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Ephedrine.Approved, Illicit
DroxidopaEphedrine may increase the hypertensive activities of Droxidopa.Approved, Investigational
DuloxetineDuloxetine may increase the tachycardic activities of Ephedrine.Approved
EnfluraneEphedrine may increase the arrhythmogenic activities of Enflurane.Approved, Vet Approved
EpanololThe risk or severity of adverse effects can be increased when Ephedrine is combined with Epanolol.Experimental
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Ephedrine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Ephedrine.Approved
ErgonovineErgonovine may increase the hypertensive activities of Ephedrine.Approved
ErgotamineErgotamine may increase the hypertensive activities of Ephedrine.Approved
EtilefrineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Etilefrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Ephedrine.Approved
FenozoloneThe risk or severity of adverse effects can be increased when Ephedrine is combined with Fenozolone.Experimental
HalothaneEphedrine may increase the arrhythmogenic activities of Halothane.Approved, Vet Approved
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Hydroxyamphetamine.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Ephedrine.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Ephedrine.Approved
IsofluraneEphedrine may increase the arrhythmogenic activities of Isoflurane.Approved, Vet Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Ephedrine.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Isoxsuprine.Approved, Withdrawn
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Ephedrine.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Ephedrine.Approved
LinezolidLinezolid may increase the hypertensive activities of Ephedrine.Approved, Investigational
MefenorexThe risk or severity of adverse effects can be increased when Ephedrine is combined with Mefenorex.Experimental
MephentermineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Mephentermine.Approved
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ephedrine.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Methamphetamine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Ephedrine.Approved
MethoxyfluraneEphedrine may increase the arrhythmogenic activities of Methoxyflurane.Approved, Vet Approved
MethylergometrineMethylergometrine may increase the hypertensive activities of Ephedrine.Approved
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Ephedrine.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Ephedrine.Approved
NabiloneNabilone may increase the tachycardic activities of Ephedrine.Approved, Investigational
Nitrous oxideEphedrine may increase the arrhythmogenic activities of Nitrous oxide.Approved, Vet Approved
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Ephedrine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Ephedrine is combined with Nylidrin.Approved
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Ephedrine.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Ephedrine.Approved
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Ephedrine.Approved, Illicit
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Ephedrine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Ephedrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Ephedrine.Approved, Vet Approved, Withdrawn
PrazosinPrazosin may decrease the vasoconstricting activities of Ephedrine.Approved
PrenalterolThe risk or severity of adverse effects can be increased when Ephedrine is combined with Prenalterol.Experimental
ProcaterolThe risk or severity of adverse effects can be increased when Ephedrine is combined with Procaterol.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Pseudoephedrine.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Racepinephrine.Approved
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Ephedrine.Approved
SevofluraneEphedrine may increase the arrhythmogenic activities of Sevoflurane.Approved, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Ephedrine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Ephedrine.Approved
SynephrineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Synephrine.Experimental
TamsulosinTamsulosin may decrease the vasoconstricting activities of Ephedrine.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Ephedrine.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Ephedrine.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Ephedrine.Approved
TetryzolineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Tetryzoline.Approved
TramazolineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Tramazoline.Investigational
TretoquinolThe risk or severity of adverse effects can be increased when Ephedrine is combined with Tretoquinol.Experimental
TrichloroethyleneEphedrine may increase the arrhythmogenic activities of Trichloroethylene.Experimental
TrimazosinTrimazosin may decrease the vasoconstricting activities of Ephedrine.Experimental
TyramineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Tyramine.Investigational, Nutraceutical
UrapidilUrapidil may decrease the vasoconstricting activities of Ephedrine.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of Ephedrine.Approved
XenonEphedrine may increase the arrhythmogenic activities of Xenon.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Thomas Moest, Uwe Loeffler, Hans Waiblinger, "Production of pellets composed of an ephedrine derivative." U.S. Patent US5453280, issued March, 1994.

US5453280
General References
Not Available
External Links
Human Metabolome Database
HMDB15451
KEGG Drug
D00124
KEGG Compound
C01575
PubChem Compound
9294
PubChem Substance
46507538
ChemSpider
8935
ChEBI
15407
ChEMBL
CHEMBL211456
Therapeutic Targets Database
DAP000228
PharmGKB
PA449466
IUPHAR
556
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ephedrine
ATC Codes
R01AA03 — EphedrineC01CA26 — EphedrineR03CA02 — EphedrineR01AB05 — EphedrineS01FB02 — EphedrineA08AA56 — Ephedrine, combinations
AHFS Codes
  • 12:12.00
  • 12:12.12
  • 92:01.00*
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2Unknown StatusTreatmentMyasthenic Syndromes, Congenital1
2CompletedPreventionArterial Hypotension / Valve Surgery1
2CompletedPreventionCesarean Section / Nausea / Vomiting1
2CompletedPreventionCoagulation Defect; Bleeding1
2CompletedTreatmentBMI >30 kg/m21
2Not Yet RecruitingPreventionPost Anaesthetic Shivering1
2, 3Active Not RecruitingTreatmentArterial Hypotension1
2, 3RecruitingPreventionPost-operative Cognitive Dysfunction1
2, 3RecruitingPreventionSpinal Hypotension1
3CompletedBasic ScienceBMI >30 kg/m21
3CompletedTreatmentAnaesthesia therapy1
3CompletedTreatmentElective Caesarean Section Surgeries1
3Unknown StatusNot AvailableInduction of Total Intravenous General Anesthesia1
3WithdrawnTreatmentPreeclampsia / Pregnancy Toxemias1
4CompletedPreventionBradycardia1
4CompletedPreventionLabour Pain1
4CompletedTreatmentArterial Hypotension / Cesarean Section / Pregnancy / Spinal Anaesthesia1
4CompletedTreatmentComplications; Cesarean Section1
4CompletedTreatmentGall Stone Disease1
4RecruitingPreventionAnesthesia; Adverse Effect, Spinal and Epidural / Arterial Hypotension / Complications; Cesarean Section1
4RecruitingTreatmentBrain Microcirculation and Oxygenation / Neoplasms, Brain1
4RecruitingTreatmentProphylaxis of preeclampsia1
4TerminatedTreatmentPregnancy / Spinal Anaesthesia1
4Unknown StatusNot AvailableEndovascular Carotid Surgery / Preoperative Hypotension1
Not AvailableCompletedBasic ScienceBMI >30 kg/m21
Not AvailableCompletedPreventionAnesthesia; Adverse Effect, Spinal and Epidural1
Not AvailableCompletedPreventionBMI >30 kg/m21
Not AvailableCompletedTreatmentArterial Hypotension / Complications; Cesarean Section / Obstetrical Complication of Anesthesia1
Not AvailableCompletedTreatmentArterial Hypotension / Preeclampsia1
Not AvailableCompletedTreatmentBody Temperature Changes1
Not AvailableCompletedTreatmentCesarean Section / Spinal Anaesthesia1
Not AvailableCompletedTreatmentFractures, Compression1
Not AvailableCompletedTreatmentObesity, Morbid1
Not AvailableEnrolling by InvitationNot AvailableArterial Hypotension1
Not AvailableNot Yet RecruitingPreventionArterial Hypotension / Hip Fractures1
Not AvailableRecruitingPreventionArterial Hypotension1
Not AvailableRecruitingPreventionArterial Hypotension / Complications; Cesarean Section1
Not AvailableRecruitingPreventionGastrointestinal Bleedings / Gastrointestinal Diseases1
Not AvailableRecruitingTreatmentCesarean Section / Prophylaxis of preeclampsia1
Not AvailableUnknown StatusBasic ScienceBMI >30 kg/m2 / Cardiovascular Disease (CVD) / Type 2 Diabetes Mellitus1
Not AvailableUnknown StatusDiagnosticPreeclampsia1
Not AvailableUnknown StatusTreatmentCarotid Stenosis / Intra-operative Hypotension1
Not AvailableUnknown StatusTreatmentArterial hypoxia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
InjectionIntravenous50 mg/mL
OintmentNasal
SyrupOral
TabletOral
Tablet, coatedOral
Injection, solutionIntramuscular; Intravenous; Subcutaneous50 mg/mL
Injection, solutionIntravenous10 mg/mL
CapsuleOral25 mg
TabletOral8 mg
TabletOral25 mg
CapsuleOral25 mg/1
InjectionIntramuscular; Intravenous; Subcutaneous50 mg/mL
Injection, solutionIntravenous50 mg/mL
SolutionIntramuscular; Subcutaneous50 mg
LiquidIntramuscular; Intravenous; Subcutaneous50 mg
SolutionIntramuscular; Intravenous; Subcutaneous50 mg
TabletOral15 mg
TabletOral30 mg
TabletOral.13 mg
LiquidNasal1.5 %
LiquidOral
JellyNasal
TabletOral10 mg
LiquidInfiltration
LiquidInfiltration; Subcutaneous
Prices
Unit descriptionCostUnit
Ephedrine sulfate 250 mg/5 ml7.82USD ml
Ephedrine-ns 50 mg/5 ml syr2.91USD ml
Ephedrine-ns 100 mg/10 ml syr2.07USD ml
Ephedrine su 50 mg/ml vial1.75USD ml
Ephedrine 50 mg/ml ampul0.76USD ml
Ephedrine powder0.47USD g
Ephedrine sulfate powder0.46USD g
Ephedrine su 25 mg capsule0.3USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)34 °CPhysProp
boiling point (°C)255 °CPhysProp
water solubility6.36E+004 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.13AVDEEF,A (1997)
pKa10.3 (at 0 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility8.26 mg/mLALOGPS
logP1ALOGPS
logP1.32ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.69 m3·mol-1ChemAxon
Polarizability18.8 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9645
Blood Brain Barrier+0.5638
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.7182
P-glycoprotein inhibitor INon-inhibitor0.9795
P-glycoprotein inhibitor IINon-inhibitor0.984
Renal organic cation transporterNon-inhibitor0.8965
CYP450 2C9 substrateNon-substrate0.8001
CYP450 2D6 substrateNon-substrate0.7839
CYP450 3A4 substrateNon-substrate0.7235
CYP450 1A2 substrateNon-inhibitor0.5595
CYP450 2C9 inhibitorNon-inhibitor0.7209
CYP450 2D6 inhibitorInhibitor0.5846
CYP450 2C19 inhibitorNon-inhibitor0.5737
CYP450 3A4 inhibitorNon-inhibitor0.9431
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.907
Ames testNon AMES toxic0.9517
CarcinogenicityNon-carcinogens0.7739
BiodegradationNot ready biodegradable0.7807
Rat acute toxicity2.3882 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9329
hERG inhibition (predictor II)Non-inhibitor0.9277
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.84 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9000000000-bcc578719d003732d7f8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-33d551e262321705ae8a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0900000000-32a84e7b7e5332fe2026
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-82640acc94773485568a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-bdfb6079227a418eb706
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-c04df5fb623578be67ea
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00l2-1900000000-3a68bc210684b52a9fd8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-2900000000-e12bf9df640426404f1c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0900000000-0218a677989aab76b176
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-3dd538034653edb47df1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-553c930e0970a8c1a866
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-0499cdf7955d013fca29
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-015a-1900000000-f6b6229ef8c2d7fd24ab
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-2900000000-7c8549f8cd727886d67d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-bcbf5073df33d11415cc

Taxonomy

Description
This compound 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
Aralkylamines / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Phenylpropane / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Secondary aliphatic amine / Secondary amine / Alcohol / Organopnictogen compound / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenylethanolamines, phenethylamine alkaloid (CHEBI:15407) / Alkaloids, Phenylalanine derived alkaloids (C01575)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inverse agonist
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Kobayashi S, Endou M, Sakuraya F, Matsuda N, Zhang XH, Azuma M, Echigo N, Kemmotsu O, Hattori Y, Gando S: The sympathomimetic actions of l-ephedrine and d-pseudoephedrine: direct receptor activation or norepinephrine release? Anesth Analg. 2003 Nov;97(5):1239-45. [PubMed:14570629]
  2. McMahon LR, Cunningham KA: Discriminative stimulus effects of (-)-ephedrine in rats: analysis with catecholamine transporter and receptor ligands. Drug Alcohol Depend. 2003 Jun 5;70(3):255-64. [PubMed:12757963]
  3. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. [PubMed:17209801]
  4. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Ma G, Bavadekar SA, Davis YM, Lalchandani SG, Nagmani R, Schaneberg BT, Khan IA, Feller DR: Pharmacological effects of ephedrine alkaloids on human alpha(1)- and alpha(2)-adrenergic receptor subtypes. J Pharmacol Exp Ther. 2007 Jul;322(1):214-21. Epub 2007 Apr 3. [PubMed:17405867]
  2. Wellman PJ, Miller DK, Ho DH: Noradrenergic modulation of ephedrine-induced hypophagia. Synapse. 2003 Apr;48(1):18-24. [PubMed:12557268]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. Ellis JD, German CL, Birdsall E, Hanson JE, Crosby MA, Rowley SD, Sawada NA, West JN, Hanson GR, Fleckenstein AE: Ephedrine decreases vesicular monoamine transporter-2 function. Synapse. 2011 May;65(5):449-51. doi: 10.1002/syn.20896. [PubMed:21370280]
  2. Horton DB, Siripurapu KB, Norrholm SD, Culver JP, Hojahmat M, Beckmann JS, Harrod SB, Deaciuc AG, Bardo MT, Crooks PA, Dwoskin LP: meso-Transdiene analogs inhibit vesicular monoamine transporter-2 function and methamphetamine-evoked dopamine release. J Pharmacol Exp Ther. 2011 Mar;336(3):940-51. doi: 10.1124/jpet.110.175117. Epub 2010 Dec 21. [PubMed:21177475]
  3. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613]
  4. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [PubMed:7751968]
  5. Yasumoto S, Tamura K, Karasawa J, Hasegawa R, Ikeda K, Yamamoto T, Yamamoto H: Inhibitory effect of selective serotonin reuptake inhibitors on the vesicular monoamine transporter 2. Neurosci Lett. 2009 May 1;454(3):229-32. doi: 10.1016/j.neulet.2009.03.049. Epub 2009 Mar 18. [PubMed:19429089]
  6. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. [PubMed:17209801]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Singh AK, Spassova D: Effects of hexamethonium, phenothiazines, propranolol and ephedrine on acetylcholinesterase carbamylation by physostigmine, aldicarb and carbaryl: interaction between the active site and the functionally distinct peripheral sites in acetylcholinesterase. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Jan;119(1):97-105. [PubMed:9568379]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. Maizel' EB, Rozengart EV, Khakimov IuP, Abduvakhabov AA, Aslanov KhA: [Ephedrine, salsoline and cytisine derivatives as substrates and inhibitirs of cholinesterases]. Biokhimiia. 1978 Jul;43(7):1150-6. [PubMed:698301]

Drug created on July 06, 2007 13:56 / Updated on October 11, 2017 19:32