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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2023-02-21 17:18:16 UTC

HMDB ID

HMDB0014748

Secondary Accession Numbers

HMDB14748

Metabolite Identification

Common Name

Metaraminol

Description

Metaraminol is only found in individuals that have used or taken this drug. It is an adrenergic agonist that acts predominantly at alpha adrenergic receptors and also stimulates the release of norepinephrine. It has been used primarily as a vasoconstrictor in the treatment of hypotension. [PubChem]Metaraminol acts through peripheral vasoconstriction by acting as a pure alpha-1 adrenergic receptor agonist, consequently increasing systemic blood pressure (both systolic & diastolic). Its effect is thought to be associated with the inhibition of adenyl cyclase which leads to an inhibition of the production of cAMP. Another effect of Metaraminol is that it releases norepinephrine from its storage sites indirectly.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 610                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.414   2.164   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.226   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.081   3.704   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.748   1.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   2.164   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -0.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   1.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -0.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -0.916   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -2.456   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -2.456   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -3.226   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2   10                                                            
CONECT    3    5                                                            
CONECT    4    1    5    6                                                  
CONECT    5    3    4    7                                                  
CONECT    6    4    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6   10                                                       
CONECT    9    6   11                                                       
CONECT   10    2    8   12                                                  
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Erythro-metaraminol	ChEBI
1-(m-Hydroxyphenyl)-2-amino-1-propanol	ChEBI
1-Metaraminol	ChEBI
2-Amino-1-(m-hydroxyphenyl)-1-propanol	ChEBI
3-Hydroxyphenylisopropanolamine	ChEBI
alpha-(1-Aminoethyl)-3-hydroxybenzenemethanol	ChEBI
alpha-(m-Hydroxyphenyl)-beta-aminopropanol	ChEBI
Hydroxynorephedrine	ChEBI
L-Metaraminol	ChEBI
m-Hydroxy norephedrine	ChEBI
m-Hydroxyphenylpropanolamine	ChEBI
m-Hydroxypropadrine	ChEBI
Metaraminolum	ChEBI
a-(1-Aminoethyl)-3-hydroxybenzenemethanol	Generator
Α-(1-aminoethyl)-3-hydroxybenzenemethanol	Generator
a-(m-Hydroxyphenyl)-b-aminopropanol	Generator
Α-(m-hydroxyphenyl)-β-aminopropanol	Generator
Metaraminol bitartrate	HMDB
Araminol	HMDB
Bitartrate, metaraminol	HMDB
Merck sharp and dohme brand OF metaraminol bitartrate	HMDB
Metaradrin	HMDB
Metaraminol tartrate	HMDB
m-Hydroxynorephedrine	HMDB
Isophenylephrine	HMDB
Meta hydroxynorephedrine	HMDB
Meta-hydroxynorephedrine	HMDB
Aramine	HMDB
Merck brand OF metaraminol bitartrate	HMDB
Tartrate, metaraminol	HMDB
m Hydroxynorephedrine	HMDB
Metaraminol bitartrate (1:1)	HMDB
Hydroxyphenylpropanolamine	HMDB
m Hydroxyphenylpropanolamine	HMDB

Chemical Formula

C₉H₁₃NO₂

Average Molecular Weight

167.205

Monoisotopic Molecular Weight

167.094628665

IUPAC Name

3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol

Traditional Name

metaraminol

CAS Registry Number

54-49-9

SMILES

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

InChI Identifier

InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1

InChI Key

WXFIGDLSSYIKKV-RCOVLWMOSA-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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Organic nitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Primary amine
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethanolamines (CHEBI:6794 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014748)

Source

Exogenous

Exogenous (HMDB: HMDB0014748)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	107.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	12.8 g/L	Not Available
LogP	0.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.8 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	-0.045	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	17.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.386	31661259
DarkChem	[M-H]-	137.131	31661259
DeepCCS	[M+H]+	142.634	30932474
DeepCCS	[M-H]-	140.238	30932474
DeepCCS	[M-2H]-	173.55	30932474
DeepCCS	[M+Na]+	148.547	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]-	136.1	32859911
AllCCS	[M+Na-2H]-	137.3	32859911
AllCCS	[M+HCOO]-	138.7	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.	1.74 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8701 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.17 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	215.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	507.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	261.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	86.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	262.0 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	251.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	672.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	604.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	53.0 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	610.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	157.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	542.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	479.4 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	165.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metaraminol	C[C@H](N)[C@H](O)C1=CC(O)=CC=C1	3025.2	Standard polar	33892256
Metaraminol	C[C@H](N)[C@H](O)C1=CC(O)=CC=C1	1680.1	Standard non polar	33892256
Metaraminol	C[C@H](N)[C@H](O)C1=CC(O)=CC=C1	1762.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Metaraminol,1TMS,isomer #1	C[C@H](N)[C@H](O[Si](C)(C)C)C1=CC=CC(O)=C1	1753.1	Semi standard non polar	33892256
Metaraminol,1TMS,isomer #2	C[C@H](N)[C@H](O)C1=CC=CC(O[Si](C)(C)C)=C1	1687.8	Semi standard non polar	33892256
Metaraminol,1TMS,isomer #3	C[C@H](N[Si](C)(C)C)[C@H](O)C1=CC=CC(O)=C1	1797.9	Semi standard non polar	33892256
Metaraminol,2TMS,isomer #1	C[C@H](N)[C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1717.1	Semi standard non polar	33892256
Metaraminol,2TMS,isomer #2	C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1=CC=CC(O)=C1	1757.2	Semi standard non polar	33892256
Metaraminol,2TMS,isomer #3	C[C@H](N[Si](C)(C)C)[C@H](O)C1=CC=CC(O[Si](C)(C)C)=C1	1764.3	Semi standard non polar	33892256
Metaraminol,2TMS,isomer #4	C[C@@H]([C@H](O)C1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	1935.0	Semi standard non polar	33892256
Metaraminol,3TMS,isomer #1	C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1783.2	Semi standard non polar	33892256
Metaraminol,3TMS,isomer #1	C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1796.3	Standard non polar	33892256
Metaraminol,3TMS,isomer #1	C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1838.1	Standard polar	33892256
Metaraminol,3TMS,isomer #2	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	1938.7	Semi standard non polar	33892256
Metaraminol,3TMS,isomer #2	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	1942.4	Standard non polar	33892256
Metaraminol,3TMS,isomer #2	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	1940.6	Standard polar	33892256
Metaraminol,3TMS,isomer #3	C[C@@H]([C@H](O)C1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	1925.2	Semi standard non polar	33892256
Metaraminol,3TMS,isomer #3	C[C@@H]([C@H](O)C1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	1891.8	Standard non polar	33892256
Metaraminol,3TMS,isomer #3	C[C@@H]([C@H](O)C1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2066.0	Standard polar	33892256
Metaraminol,4TMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2044.8	Semi standard non polar	33892256
Metaraminol,4TMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	1918.4	Standard non polar	33892256
Metaraminol,4TMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	1840.6	Standard polar	33892256
Metaraminol,1TBDMS,isomer #1	C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	1978.5	Semi standard non polar	33892256
Metaraminol,1TBDMS,isomer #2	C[C@H](N)[C@H](O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	1933.7	Semi standard non polar	33892256
Metaraminol,1TBDMS,isomer #3	C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)C1=CC=CC(O)=C1	2008.3	Semi standard non polar	33892256
Metaraminol,2TBDMS,isomer #1	C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2190.5	Semi standard non polar	33892256
Metaraminol,2TBDMS,isomer #2	C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	2222.0	Semi standard non polar	33892256
Metaraminol,2TBDMS,isomer #3	C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2272.3	Semi standard non polar	33892256
Metaraminol,2TBDMS,isomer #4	C[C@@H]([C@H](O)C1=CC=CC(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2350.3	Semi standard non polar	33892256
Metaraminol,3TBDMS,isomer #1	C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2460.3	Semi standard non polar	33892256
Metaraminol,3TBDMS,isomer #1	C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2400.4	Standard non polar	33892256
Metaraminol,3TBDMS,isomer #1	C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2246.9	Standard polar	33892256
Metaraminol,3TBDMS,isomer #2	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2595.0	Semi standard non polar	33892256
Metaraminol,3TBDMS,isomer #2	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2560.6	Standard non polar	33892256
Metaraminol,3TBDMS,isomer #2	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2271.1	Standard polar	33892256
Metaraminol,3TBDMS,isomer #3	C[C@@H]([C@H](O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2651.2	Semi standard non polar	33892256
Metaraminol,3TBDMS,isomer #3	C[C@@H]([C@H](O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2524.4	Standard non polar	33892256
Metaraminol,3TBDMS,isomer #3	C[C@@H]([C@H](O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2387.0	Standard polar	33892256
Metaraminol,4TBDMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2901.5	Semi standard non polar	33892256
Metaraminol,4TBDMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2681.2	Standard non polar	33892256
Metaraminol,4TBDMS,isomer #1	C[C@@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2290.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metaraminol GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9500000000-19e4ba301696c4b31705	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metaraminol GC-MS (2 TMS) - 70eV, Positive	splash10-00kb-2920000000-b05bd4da1530670783f5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metaraminol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metaraminol LC-ESI-QQ , positive-QTOF	splash10-0uxr-0900000000-54fdef7fb806e9618517	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metaraminol LC-ESI-QQ , positive-QTOF	splash10-0udi-1900000000-53aa60f30061472008e2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metaraminol LC-ESI-QQ , positive-QTOF	splash10-0a4i-3900000000-03da43641cb5f6da239a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metaraminol LC-ESI-QQ , positive-QTOF	splash10-056r-9700000000-bb18dd53ad6ac9a58e4f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metaraminol LC-ESI-QQ , positive-QTOF	splash10-004i-9300000000-3d3ebdc9e7c553d5122c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 10V, Positive-QTOF	splash10-0uxr-0900000000-cb591339823fe58da583	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 20V, Positive-QTOF	splash10-0ue9-0900000000-72d52af9c83300b1cf21	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 40V, Positive-QTOF	splash10-001i-5900000000-bf0b8aab46d5d2c3aab6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 10V, Negative-QTOF	splash10-014i-0900000000-0ed81878c7665d2668c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 20V, Negative-QTOF	splash10-00r2-0900000000-432f771c7524342b7012	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 40V, Negative-QTOF	splash10-006x-8900000000-01eebcaa27ee21836f1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 10V, Positive-QTOF	splash10-0udi-0900000000-7cfdf32533cde65b37fb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 20V, Positive-QTOF	splash10-001i-0900000000-e5f86599f7aaea978c90	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 40V, Positive-QTOF	splash10-0pvi-9600000000-1f433b6e4686c25920c0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 10V, Negative-QTOF	splash10-0002-0900000000-78917da9a8c1cc2ba5dc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 20V, Negative-QTOF	splash10-05fu-2900000000-edfa5053e3bba3a40bfa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaraminol 40V, Negative-QTOF	splash10-0006-9300000000-8cb77e21838a1ccce636	2021-10-11	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

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 DB00610	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00610	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00610

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5695

KEGG Compound ID

C07146

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metaraminol

METLIN ID

Not Available

PubChem Compound

5906

PDB ID

Not Available

ChEBI ID

6794

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

Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. [PubMed:2258979 ]
Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism]. Urologe A. 1988 Jul;27(4):225-9. [PubMed:3140463 ]
McDonald M, Santucci RA: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. Int Braz J Urol. 2004 Mar-Apr;30(2):121-2. [PubMed:15703094 ]

Enzymes

Enzyme Details

1. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Tatsuta M, Iishi H, Baba M, Yano H, Sakai N, Uehara H, Hirasawa R, Nakaizumi A: Alpha1-adrenoceptor stimulation enhances experimental gastric carcinogenesis induced by N-methyl-N'-nitro-N-nitrosoguanidine in Wistar rats. Int J Cancer. 1998 Jul 29;77(3):467-9. [PubMed:9663612 ]

Showing metabocard for Metaraminol (HMDB0014748)

MOL for HMDB0014748 (Metaraminol)

3D MOL for HMDB0014748 (Metaraminol)

3D SDF for HMDB0014748 (Metaraminol)

3D-SDF for HMDB0014748 (Metaraminol)

PDB for HMDB0014748 (Metaraminol)

3D PDB for HMDB0014748 (Metaraminol)

SMILES for HMDB0014748 (Metaraminol)

INCHI for HMDB0014748 (Metaraminol)

Structure for HMDB0014748 (Metaraminol)

3D Structure for HMDB0014748 (Metaraminol)

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