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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-12-07 02:51:12 UTC
HMDB IDHMDB0015451
Secondary Accession Numbers
  • HMDB15451
Metabolite Identification
Common NameEphedrine
DescriptionEphedrine 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.
Structure
Thumb
Synonyms
ValueSource
(1R,2S)-1-Phenyl-1-hydroxy-2-methylaminopropaneChEBI
L(-)-EphedrineChEBI
L-EphedrineChEBI
L-erythro-2-(methylamino)-1-Phenylpropan-1-olChEBI
erythro Isomer OF ephedrineMeSH
Renaudin brand OF ephedrine hydrochlorideMeSH
Renaudin, ephedrineMeSH
Ephedrine renaudinMeSH
Sal-phedrineMeSH
Sulfate, ephedrineMeSH
Ephedrine hydrochlorideMeSH
Ephedrine sulfateMeSH
Sal phedrineMeSH
SalPhedrineMeSH
Ephedrine erythro isomerMeSH
Hydrochloride, ephedrineMeSH
Wendt brand OF ephedrine sulfateMeSH
Chemical FormulaC10H15NO
Average Molecular Weight165.2322
Monoisotopic Molecular Weight165.115364107
IUPAC Name(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
Traditional Nameephedrine
CAS Registry Number299-42-3
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 KeyKWGRBVOPPLSCSI-WPRPVWTQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpropanes
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Enteral:

  Parenteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Psychiatric disorders:

    Gastrointestinal disorders:

    Nervous system disorders:

    General disorders and administration site conditions:

    Musculoskeletal and connective tissue disorders:

    Metabolism and nutrition disorders:

    Vascular disorders:

    Eye disorders:

  Observation:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point34 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility63.6 mg/mL at 30 °CNot Available
LogP1.13AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
Water Solubility8.26 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.69 m³·mol⁻¹ChemAxon
Polarizability18.8 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9300000000-5bdf33e08e94f0c0bd26View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05di-9610000000-8f364065f58e7dd69444View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-33d551e262321705ae8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0900000000-32a84e7b7e5332fe2026View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-82640acc94773485568aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-bdfb6079227a418eb706View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-c04df5fb623578be67eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00l2-1900000000-3a68bc210684b52a9fd8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0159-2900000000-e12bf9df640426404f1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0900000000-0218a677989aab76b176View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-3dd538034653edb47df1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-553c930e0970a8c1a866View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-0499cdf7955d013fca29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-015a-1900000000-f6b6229ef8c2d7fd24abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0159-2900000000-7c8549f8cd727886d67dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-bcbf5073df33d11415ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0900000000-677d622716b4c2545f16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-2900000000-416def0e527ddf116a39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9500000000-155625a572f19610e138View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ea7e1b550b5dc0d6d41dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-2900000000-f4de25860574bb60daf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9600000000-62e375458e5f83795e90View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-bcc578719d003732d7f8View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01364 details
UrineDetected and Quantified0.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01364 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-6 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01364
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8935
KEGG Compound IDC01575
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEphedrine
METLIN IDNot Available
PubChem Compound9294
PDB IDNot Available
ChEBI ID15407
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase 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
Molecular weight:
67795.525
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 ]
General function:
Involved in carboxylesterase activity
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
Molecular weight:
68417.575
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 ]
General function:
Involved in transmembrane transport
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. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular weight:
55712.1
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. 2010 Dec 15. [PubMed:21162110 ]
  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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
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 ]

Transporters

General function:
Involved in neurotransmitter: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
Molecular weight:
69331.42
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 ]