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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015289

Secondary Accession Numbers

HMDB15289

Metabolite Identification

Common Name

Bretylium

Description

Bretylium blocks the release of noradrenaline from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation. The primary mode of action for bretylium is thought to be inhibition of voltage-gated K(+) channels. Recent evidence has shown that bretylium may also inhibit the Na,K-ATPase by binding to the extracellular K-site.

Structure

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

HMDB0015289
     RDKit          3D
Bretylium
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.3610    0.1218    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -0.7936    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -0.0870   -0.2220 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.2605   -0.7946   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    1.1802   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525    0.3298    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813    0.1013    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -1.1744    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -1.3412   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -0.1936   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454    1.0725   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605    1.2211    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875    2.9773    0.5530 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    0.6801    1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    0.7576   -0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -0.5483    0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -1.4377   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057   -1.4699    0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562   -0.2980   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -0.7392   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683   -1.8734   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.8475   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724    0.8524   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189    1.5404   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    1.3022    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -0.4595    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -2.0620    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -2.3222   -0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -0.3591   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599    1.9699   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
M  CHG  1   3   1
M  END

HMDB0015289
     RDKit          3D
Bretylium
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.3610    0.1218    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -0.7936    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -0.0870   -0.2220 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.2605   -0.7946   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    1.1802   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525    0.3298    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813    0.1013    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -1.1744    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -1.3412   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -0.1936   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454    1.0725   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605    1.2211    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875    2.9773    0.5530 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    0.6801    1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    0.7576   -0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -0.5483    0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -1.4377   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057   -1.4699    0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562   -0.2980   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -0.7392   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683   -1.8734   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.8475   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724    0.8524   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189    1.5404   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    1.3022    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -0.4595    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -2.0620    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -2.3222   -0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -0.3591   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599    1.9699   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
M  CHG  1   3   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1158                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0       3.080  -0.770   0.000  0.00  0.00          Br+0
HETATM    2  N   UNK     0       7.081   1.540   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       5.748   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.415   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.311   2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.851   0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -3.850   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    3    4    5    6                                             
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    9   10                                                  
CONECT    8    4                                                            
CONECT    9    1    7   11                                                  
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0015289
HETATM    1  C1  UNL     1      -3.361   0.122   0.293  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.172  -0.794   0.088  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.974  -0.087  -0.222  1.00  0.00           N1+
HETATM    4  C3  UNL     1      -0.260  -0.795  -1.262  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.360   1.180  -0.935  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.153   0.330   0.899  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.281   0.101   0.472  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.742  -1.174   0.306  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.018  -1.341  -0.238  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.745  -0.194  -0.579  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.245   1.072  -0.389  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.961   1.221   0.161  1.00  0.00           C  
HETATM   13 BR1  UNL     1       1.287   2.977   0.553  1.00  0.00          BR  
HETATM   14  H1  UNL     1      -3.256   0.680   1.233  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.575   0.758  -0.584  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.230  -0.548   0.425  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.483  -1.438  -0.804  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.106  -1.470   0.929  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.656  -0.298  -1.614  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.982  -0.739  -2.153  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.168  -1.873  -1.063  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.860   1.848  -0.236  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.972   0.852  -1.790  1.00  0.00           H  
HETATM   24  H11 UNL     1      -0.419   1.540  -1.381  1.00  0.00           H  
HETATM   25  H12 UNL     1      -0.377   1.302   1.270  1.00  0.00           H  
HETATM   26  H13 UNL     1      -0.318  -0.460   1.690  1.00  0.00           H  
HETATM   27  H14 UNL     1       1.181  -2.062   0.660  1.00  0.00           H  
HETATM   28  H15 UNL     1       3.431  -2.322  -0.371  1.00  0.00           H  
HETATM   29  H16 UNL     1       4.720  -0.359  -1.046  1.00  0.00           H  
HETATM   30  H17 UNL     1       3.760   1.970  -0.694  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4    5    6
CONECT    4   19   20   21
CONECT    5   22   23   24
CONECT    6    7   25   26
CONECT    7    8    8   12
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13
END

HMDB0015289
     RDKit          3D
Bretylium
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.3610    0.1218    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -0.7936    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -0.0870   -0.2220 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.2605   -0.7946   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    1.1802   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525    0.3298    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813    0.1013    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -1.1744    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -1.3412   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -0.1936   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454    1.0725   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605    1.2211    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875    2.9773    0.5530 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    0.6801    1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    0.7576   -0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -0.5483    0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -1.4377   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057   -1.4699    0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562   -0.2980   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -0.7392   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683   -1.8734   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.8475   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724    0.8524   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189    1.5404   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    1.3022    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -0.4595    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -2.0620    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -2.3222   -0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -0.3591   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599    1.9699   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
M  CHG  1   3   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2-Bromobenzyl)ethyldimethylaminium	ChEBI
2-Bromo-N-ethyl-N,N-dimethylbenzenemethanaminium	ChEBI
N-Ethyl-N,N-dimethyl-2-bromobenzenemethanaminium	ChEBI
Bretylate	HMDB
Bretylium tolsylate	HMDB
Bretylium tosylate	HMDB
Bretylum	HMDB
Bretylium bromide	HMDB
Bretylium chloride	HMDB
Bretylium iodide	HMDB

Chemical Formula

C₁₁H₁₇BrN

Average Molecular Weight

243.163

Monoisotopic Molecular Weight

242.054437196

IUPAC Name

[(2-bromophenyl)methyl](ethyl)dimethylazanium

Traditional Name

bretylium

CAS Registry Number

59-41-6

SMILES

CC[N+](C)(C)CC1=CC=CC=C1Br

InChI Identifier

InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1

InChI Key

AAQOQKQBGPPFNS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylmethylamines

Alternative Parents

Substituents

Benzylamine
Phenylmethylamine
Aralkylamine
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Tetraalkylammonium salt
Quaternary ammonium salt
Amine
Organic nitrogen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organic salt
Hydrocarbon derivative
Organopnictogen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:3172 )

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: HMDB0015289)

Source

Exogenous

Exogenous (HMDB: HMDB0015289)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00015 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	140.573	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000839

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.1	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	17.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.89 m³·mol⁻¹	ChemAxon
Polarizability	23.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	133.198	30932474
DeepCCS	[M-H]-	130.803	30932474
DeepCCS	[M-2H]-	166.444	30932474
DeepCCS	[M+Na]+	141.282	30932474
AllCCS	[M+H]+	148.3	32859911
AllCCS	[M+H-H2O]+	144.6	32859911
AllCCS	[M+NH4]+	151.8	32859911
AllCCS	[M+Na]+	152.8	32859911
AllCCS	[M-H]-	159.2	32859911
AllCCS	[M+Na-2H]-	160.6	32859911
AllCCS	[M+HCOO]-	162.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bretylium	CC[N+](C)(C)CC1=CC=CC=C1Br	1993.1	Standard polar	33892256
Bretylium	CC[N+](C)(C)CC1=CC=CC=C1Br	1387.2	Standard non polar	33892256
Bretylium	CC[N+](C)(C)CC1=CC=CC=C1Br	1505.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bretylium GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-9660000000-f1a790c5dc75745515bf	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bretylium GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bretylium 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bretylium 10V, Positive-QTOF	splash10-0006-0090000000-4aeb2988fef6edbee36e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bretylium 20V, Positive-QTOF	splash10-03xr-0390000000-a00c3f0ed8c3aa8c892a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bretylium 40V, Positive-QTOF	splash10-014i-2910000000-431fec477d416b1fea58	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart 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 DB01158	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01158	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01158

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2337

KEGG Compound ID

C06855

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bretylium

METLIN ID

Not Available

PubChem Compound

2431

PDB ID

Not Available

ChEBI ID

3172

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. Sodium/potassium-transporting ATPase subunit alpha-1

General function:: Involved in ATP binding
Specific function:: This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:: ATP1A1
Uniprot ID:: P05023
Molecular weight:: 112895.01

References

Dzimiri N, Almotrefi AA: Inhibition of myocardial Na(+)-K(+)-ATPase activity by bretylium: role of potassium. Arch Int Pharmacodyn Ther. 1992 Jul-Aug;318:76-85. [PubMed:1334399 ]
Helms JB, Arnett KL, Gatto C, Milanick MA: Bretylium, an organic quaternary amine, inhibits the Na,K-ATPase by binding to the extracellular K-site. Blood Cells Mol Dis. 2004 May-Jun;32(3):394-400. [PubMed:15121098 ]
Dzimiri N, Almotrefi AA: Interaction of bretylium tosylate with guinea-pig myocardial Na(+)-K(+)-ATPase. Gen Pharmacol. 1991;22(5):935-8. [PubMed:1662173 ]
Tiku PE, Nowell PT: Selective inhibition of K(+)-stimulation of Na,K-ATPase by bretylium. Br J Pharmacol. 1991 Dec;104(4):895-900. [PubMed:1667290 ]

Showing metabocard for Bretylium (HMDB0015289)

MOL for HMDB0015289 (Bretylium)

3D MOL for HMDB0015289 (Bretylium)

3D SDF for HMDB0015289 (Bretylium)

3D-SDF for HMDB0015289 (Bretylium)

PDB for HMDB0015289 (Bretylium)

3D PDB for HMDB0015289 (Bretylium)

SMILES for HMDB0015289 (Bretylium)

INCHI for HMDB0015289 (Bretylium)

Structure for HMDB0015289 (Bretylium)

3D Structure for HMDB0015289 (Bretylium)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References