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Showing metabocard for Butyrylcholine (HMDB0013223)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-11-30 15:51:15 UTC
Update Date2020-04-30 16:28:36 UTC
HMDB IDHMDB0013223
Secondary Accession Numbers
  • HMDB13223
Metabolite Identification
Common NameButyrylcholine
DescriptionButyrylcholine belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Butyrylcholine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Butyrylcholine is a synthetic compound and does not occur in the body naturally. It is used as a tool to distinguish between acetyl- and butyrylcholinesterase. Butyrylcholine is an acetylcholine-like molecule, with activation of some of the same receptors as acetylcholine. It is hydrolyzed by acetylcholinesterase and butyrylcholinesterase (also known as pseudocholinesterase), with butyrylcholinesterase being more efficient than acetylcholinesterase. Butyrylcholine is a nicotinic receptor agonist and mimics the action of acetylcholine (ACh) at both enteric and epithelial nicotinic acetylcholine receptors (nAChRs). Additionally, butyrylcholine is also able to stimulate muscarinic acetylcholine receptors (mAChRs) (PMID: 6481626 , 27423041 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013223 (Butyrylcholine)

  Mrv1652304302018042D          

 12 11  0  0  0  0            999 V2000
 9998.6249 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9100 9999.7745    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9999.3398 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1909 9999.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.910010000.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.055610000.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0554 9999.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7691 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4848 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.769110000.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.2006 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9143 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  CHG  1   2   1
M  END
Download

3D MOL for HMDB0013223 (Butyrylcholine)

HMDB0013223
     RDKit          3D
Butyrylcholine
 32 31  0  0  0  0  0  0  0  0999 V2000
    4.8152   -0.2010   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    0.1175    0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010    0.0311   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3225    0.3459    0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414    1.5308    0.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -0.6907    1.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -0.4799    1.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5701    0.3835    1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.0007    0.3715 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5627   -0.0152   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    1.0149    0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053   -1.2602    0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -1.2898   -0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5152    0.2778   -1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7680    0.2515   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -0.6160    1.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568    1.1542    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -0.9596   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3608    0.8120   -1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847   -1.4773    2.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    0.0220    2.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    1.4009    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096    0.5843    2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696   -0.8898   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703   -0.1058   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533    0.9404   -0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523    1.9783    0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556    1.2057   -0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3111    0.7224    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634   -1.2937   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5940   -1.3490    1.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3778   -2.1444    0.3776 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
M  CHG  1   9   1
M  END
Download

3D SDF for HMDB0013223 (Butyrylcholine)

  Mrv1652304302018042D          

 12 11  0  0  0  0            999 V2000
 9998.6249 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9100 9999.7745    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9999.3398 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1909 9999.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.910010000.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.055610000.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0554 9999.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7691 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4848 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.769110000.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.2006 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9143 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
HMDB0013223

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C9H20NO2/c1-5-6-9(11)12-8-7-10(2,3)4/h5-8H2,1-4H3/q+1

> <INCHI_KEY>
YRIBGSCJIMXMPJ-UHFFFAOYSA-N

> <FORMULA>
C9H20NO2

> <MOLECULAR_WEIGHT>
174.2606

> <EXACT_MASS>
174.149403889

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
20.726997717196653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-(butanoyloxy)ethyl]trimethylazanium

> <ALOGPS_LOGP>
-2.52

> <JCHEM_LOGP>
-3.076039240471746

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-7.047066258269654

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
60.5734

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyrylcholine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0013223 (Butyrylcholine)

HMDB0013223
     RDKit          3D
Butyrylcholine
 32 31  0  0  0  0  0  0  0  0999 V2000
    4.8152   -0.2010   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    0.1175    0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010    0.0311   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3225    0.3459    0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414    1.5308    0.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -0.6907    1.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -0.4799    1.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5701    0.3835    1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.0007    0.3715 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5627   -0.0152   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    1.0149    0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053   -1.2602    0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -1.2898   -0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5152    0.2778   -1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7680    0.2515   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -0.6160    1.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568    1.1542    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -0.9596   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3608    0.8120   -1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847   -1.4773    2.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    0.0220    2.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    1.4009    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096    0.5843    2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696   -0.8898   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703   -0.1058   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533    0.9404   -0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523    1.9783    0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556    1.2057   -0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3111    0.7224    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634   -1.2937   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5940   -1.3490    1.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3778   -2.1444    0.3776 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
M  CHG  1   9   1
M  END
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PDB for HMDB0013223 (Butyrylcholine)

HEADER    PROTEIN                                 30-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-20         0                                  
HETATM    1  C   UNK     0    8664.1008665.477   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8662.7658666.246   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0    8665.4348666.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8661.4238665.473   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.7658667.785   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8661.1708667.169   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8666.7708665.477   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8668.1028666.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.4388665.477   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8668.1028667.785   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8670.7748666.246   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8672.1078665.477   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5    6                                             
CONECT    3    1    7                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0013223 (Butyrylcholine)

COMPND    HMDB0013223
HETATM    1  C1  UNL     1       4.815  -0.201  -0.660  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.722   0.117   0.344  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.401   0.031  -0.433  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.323   0.346   0.558  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.141   1.531   0.918  1.00  0.00           O  
HETATM    6  O2  UNL     1       0.549  -0.691   1.051  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.483  -0.480   1.983  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.570   0.384   1.506  1.00  0.00           C  
HETATM    9  N1  UNL     1      -2.316  -0.001   0.371  1.00  0.00           N1+
HETATM   10  C7  UNL     1      -1.563  -0.015  -0.855  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.373   1.015   0.194  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.005  -1.260   0.482  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.939  -1.290  -0.757  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.515   0.278  -1.610  1.00  0.00           H  
HETATM   15  H3  UNL     1       5.768   0.251  -0.333  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.753  -0.616   1.159  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.857   1.154   0.679  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.250  -0.960  -0.872  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.361   0.812  -1.201  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.785  -1.477   2.353  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.006   0.022   2.869  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.149   1.401   1.298  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.310   0.584   2.339  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.870  -0.890  -0.835  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.270  -0.106  -1.726  1.00  0.00           H  
HETATM   26  H14 UNL     1      -1.053   0.940  -0.950  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.052   1.978   0.656  1.00  0.00           H  
HETATM   28  H16 UNL     1      -3.556   1.206  -0.877  1.00  0.00           H  
HETATM   29  H17 UNL     1      -4.311   0.722   0.689  1.00  0.00           H  
HETATM   30  H18 UNL     1      -3.763  -1.294  -0.326  1.00  0.00           H  
HETATM   31  H19 UNL     1      -3.594  -1.349   1.436  1.00  0.00           H  
HETATM   32  H20 UNL     1      -2.378  -2.144   0.378  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   11   12
CONECT   10   24   25   26
CONECT   11   27   28   29
CONECT   12   30   31   32
END
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SMILES for HMDB0013223 (Butyrylcholine)

CCCC(=O)OCC[N+](C)(C)C
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INCHI for HMDB0013223 (Butyrylcholine)

InChI=1S/C9H20NO2/c1-5-6-9(11)12-8-7-10(2,3)4/h5-8H2,1-4H3/q+1
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Synonyms
ValueSource
(2-Butyryloxy-ethyl)-trimethyl-ammoniumHMDB
N,N,N-Trimethyl-2-(1-oxobutoxy)ethanaminiumHMDB
ButyrylcholineHMDB
Chemical FormulaC9H20NO2
Average Molecular Weight174.2606
Monoisotopic Molecular Weight174.149403889
IUPAC Name[2-(butanoyloxy)ethyl]trimethylazanium
Traditional Namebutyrylcholine
CAS Registry Number3922-86-9
SMILES
CCCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C9H20NO2/c1-5-6-9(11)12-8-7-10(2,3)4/h5-8H2,1-4H3/q+1
InChI KeyYRIBGSCJIMXMPJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentAcyl cholines
Alternative Parents
Substituents
  • Acyl choline
  • Fatty acid ester
  • Fatty acyl
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029342
KNApSAcK IDNot Available
Chemspider ID16312
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButyrylcholine
METLIN IDNot Available
PubChem Compound17233
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Andreev AA, Veprintsev BN, Vulfius CA: Two-component desensitization of nicotinic receptors induced by acetylcholine agonists in Lymnaea stagnalis neurones. J Physiol. 1984 Aug;353:375-91. doi: 10.1113/jphysiol.1984.sp015341. [PubMed:6481626 ]
  2. Moreno S, Gerbig S, Schulz S, Spengler B, Diener M, Bader S: Epithelial propionyl- and butyrylcholine as novel regulators of colonic ion transport. Br J Pharmacol. 2016 Sep;173(18):2766-79. doi: 10.1111/bph.13555. Epub 2016 Aug 10. [PubMed:27423041 ]