Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2023-02-21 17:18:30 UTC

HMDB ID

HMDB0015451

Secondary Accession Numbers

HMDB15451

Metabolite Identification

Common Name

Ephedrine

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1364                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   1.540   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.748   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    3    9                                                       
CONECT    3    2    4    6                                                  
CONECT    4    1    3    5                                                  
CONECT    5    4    7    8                                                  
CONECT    6    3                                                            
CONECT    7    5   10                                                       
CONECT    8    5   11                                                       
CONECT    9    2                                                            
CONECT   10    7   12                                                       
CONECT   11    8   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0015451
HETATM    1  C1  UNL     1      -2.893   1.475  -0.148  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.630   0.952   0.326  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.511  -0.468   0.112  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.536  -0.882  -1.321  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.314  -0.991   0.829  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.388  -0.815   2.226  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.981  -0.477   0.356  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.159  -0.926   0.952  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.389  -0.470   0.560  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.452   0.456  -0.452  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.307   0.915  -1.057  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.071   0.439  -0.642  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.220   0.951  -1.054  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.670   1.466   0.648  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.723   2.538  -0.417  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.593   1.122   1.355  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.446  -0.921   0.615  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.268  -1.733  -1.448  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.768  -0.074  -2.040  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.552  -1.331  -1.606  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.254  -2.113   0.704  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.001   0.060   2.482  1.00  0.00           H  
HETATM   23  H11 UNL     1       2.059  -1.659   1.750  1.00  0.00           H  
HETATM   24  H12 UNL     1       4.317  -0.818   1.023  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.443   0.804  -0.748  1.00  0.00           H  
HETATM   26  H14 UNL     1       2.392   1.640  -1.846  1.00  0.00           H  
HETATM   27  H15 UNL     1       0.199   0.859  -1.164  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16
CONECT    3    4    5   17
CONECT    4   18   19   20
CONECT    5    6    7   21
CONECT    6   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   27
END

View in JSmol View NMR Assignments View Stereo Labels

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 Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

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

Traditional Name

ephedrine

CAS Registry Number

299-42-3

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 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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015451)

Process

Not Available

Role

Industrial application

Vasoconstrictor agent (HMDB: HMDB0015451)
Sympathomimetic agent (HMDB: HMDB0015451)
Nasal decongestant (HMDB: HMDB0015451)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	34 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	63.6 mg/mL at 30 °C	Not Available
LogP	1.13	AVDEEF,A (1997)

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.056	31661259
DarkChem	[M-H]-	136.415	31661259
DeepCCS	[M+H]+	142.231	30932474
DeepCCS	[M-H]-	139.836	30932474
DeepCCS	[M-2H]-	173.25	30932474
DeepCCS	[M+Na]+	148.144	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	142.4	32859911
AllCCS	[M+Na]+	143.6	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	141.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.49 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3488 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.4 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	105.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	794.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	101.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	265.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	290.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	512.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	685.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	139.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	735.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	171.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	423.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	384.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	43.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ephedrine	CN[C@@H](C)[C@H](O)C1=CC=CC=C1	2130.9	Standard polar	33892256
Ephedrine	CN[C@@H](C)[C@H](O)C1=CC=CC=C1	1344.6	Standard non polar	33892256
Ephedrine	CN[C@@H](C)[C@H](O)C1=CC=CC=C1	1380.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ephedrine,1TMS,isomer #1	CN[C@@H](C)[C@H](O[Si](C)(C)C)C1=CC=CC=C1	1413.7	Semi standard non polar	33892256
Ephedrine,1TMS,isomer #2	C[C@@H]([C@H](O)C1=CC=CC=C1)N(C)[Si](C)(C)C	1524.2	Semi standard non polar	33892256
Ephedrine,2TMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C	1572.6	Semi standard non polar	33892256
Ephedrine,2TMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C	1556.8	Standard non polar	33892256
Ephedrine,2TMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C	1691.1	Standard polar	33892256
Ephedrine,1TBDMS,isomer #1	CN[C@@H](C)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1643.6	Semi standard non polar	33892256
Ephedrine,1TBDMS,isomer #2	C[C@@H]([C@H](O)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	1754.6	Semi standard non polar	33892256
Ephedrine,2TBDMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	2047.3	Semi standard non polar	33892256
Ephedrine,2TBDMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	1989.4	Standard non polar	33892256
Ephedrine,2TBDMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	2002.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9300000000-5bdf33e08e94f0c0bd26	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrine GC-MS (1 TMS) - 70eV, Positive	splash10-05di-9610000000-8f364065f58e7dd69444	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-bcc578719d003732d7f8	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-33d551e262321705ae8a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-014j-0900000000-32a84e7b7e5332fe2026	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-82640acc94773485568a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-bdfb6079227a418eb706	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-c04df5fb623578be67ea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-00l2-1900000000-3a68bc210684b52a9fd8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0159-2900000000-e12bf9df640426404f1c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-014j-0900000000-0218a677989aab76b176	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-3dd538034653edb47df1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-553c930e0970a8c1a866	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-0499cdf7955d013fca29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-015a-1900000000-f6b6229ef8c2d7fd24ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0159-2900000000-7c8549f8cd727886d67d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-bcbf5073df33d11415cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine 60V, Positive-QTOF	splash10-0002-0900000000-8df1676350e720b21d8c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine 75V, Positive-QTOF	splash10-015a-1900000000-8d8e8c6689866070b7de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine 90V, Positive-QTOF	splash10-0159-2900000000-573a202622c26aee5f4e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine 35V, Positive-QTOF	splash10-0002-0900000000-a2c5df7e718fb237fcb4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ephedrine 35V, Positive-QTOF	splash10-0002-0900000000-33d551e262321705ae8a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrine 10V, Positive-QTOF	splash10-00kb-0900000000-677d622716b4c2545f16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrine 20V, Positive-QTOF	splash10-00kb-2900000000-416def0e527ddf116a39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrine 40V, Positive-QTOF	splash10-0aou-9500000000-155625a572f19610e138	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrine 10V, Negative-QTOF	splash10-03di-0900000000-ea7e1b550b5dc0d6d41d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrine 20V, Negative-QTOF	splash10-03dj-2900000000-f4de25860574bb60daf1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrine 40V, Negative-QTOF	splash10-0a6r-9600000000-62e375458e5f83795e90	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01364	21059682	details
Urine	Detected and Quantified	0.6 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01364	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01364

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001409

Chemspider ID

8935

KEGG Compound ID

C01575

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ephedrine

METLIN ID

Not Available

PubChem Compound

9294

PDB ID

Not Available

ChEBI ID

15407

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Acetylcholinesterase

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

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 ]

Enzyme Details

2. Cholinesterase

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

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 ]

Enzyme Details

3. Synaptic vesicular amine transporter

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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Enzyme Details

4. Alpha-1A adrenergic receptor

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

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 ]
Wellman PJ, Miller DK, Ho DH: Noradrenergic modulation of ephedrine-induced hypophagia. Synapse. 2003 Apr;48(1):18-24. [PubMed:12557268 ]
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

Enzyme Details

1. Sodium-dependent noradrenaline transporter

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

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 ]
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 ]
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 ]
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 ]

Showing metabocard for Ephedrine (HMDB0015451)

MOL for HMDB0015451 (Ephedrine)

3D MOL for HMDB0015451 (Ephedrine)

3D SDF for HMDB0015451 (Ephedrine)

3D-SDF for HMDB0015451 (Ephedrine)

PDB for HMDB0015451 (Ephedrine)

3D PDB for HMDB0015451 (Ephedrine)

SMILES for HMDB0015451 (Ephedrine)

INCHI for HMDB0015451 (Ephedrine)

Structure for HMDB0015451 (Ephedrine)

3D Structure for HMDB0015451 (Ephedrine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

References

References

Transporters

References