NP-MRD: Showing NP-Card for bamipine (NP0212031)

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Record Information

Version

2.0

Created at

2022-09-05 10:33:46 UTC

Updated at

2022-09-05 10:33:46 UTC

NP-MRD ID

NP0212031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bamipine

Description

Bamipine belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine. No oral use is known. Bamipine is a very strong basic compound (based on its pKa). In humans, bamipine is involved in bamipine h1-antihistamine action. When applied topically, the maximal effect is reached after 20 to 60 minutes and lasts up to 48 hours. Allergic and hypersensitivity reactions are also rare. Bamipine is not absorbed through intact skin in relevant doses. Side effects are typical of an old (first-generation) antihistamine: Tiredness in adults, agitation in children, mydriasis (dilation of the pupils). Bamipine (trade name Soventol) is a pharmaceutical drug acting as an H1 antihistamine with anticholinergic properties. These effects are rare when bamipine is applied topically as an ointment. bamipine is found in Piper hispidum and Piper retrofractum. It is used as an antipruritic ointment.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
    5.2858   -0.0058    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733   -0.2157    0.2107 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2980   -1.0055    1.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8107   -0.9081    1.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420   -0.9074   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -0.1614   -0.0037 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    1.2613    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880    1.8633    0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064    2.6838   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0707    3.2748   -0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423    3.0591    0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027    2.2241    1.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2560    1.6387    1.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2913   -0.8833   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -0.8663   -1.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758   -1.6092   -1.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306   -2.3551   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9193   -2.3681    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589   -1.6282    0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956   -0.4219   -1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -0.8578   -1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634    0.1311   -0.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4343    0.9862    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7894   -0.7846    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6582   -0.5982    2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5861   -2.0747    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447   -1.8327    1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4470   -0.0345    1.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9289   -1.9938   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660    1.6958   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707    1.4889    1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2070    2.9233   -1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4233    3.9316   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9202    3.5217    0.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1756    2.0424    2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481    0.9904    2.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -0.2998   -2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7623   -1.6312   -2.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353   -2.9449   -0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -2.9422    1.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951   -1.6345    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0305    0.6527   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6620   -0.9114   -2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -0.5351   -1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4107   -1.9578   -0.9201 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  1  0
  5 20  1  0
 20 21  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 21  2  1  0
 13  8  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv1572004221606592D          

 21 23  0  0  0  0            999 V2000
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17  8  2  0  0  0  0
 17  9  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  2  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20  1  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC(CC1)N(CC1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2/c1-20-14-12-19(13-15-20)21(18-10-6-3-7-11-18)16-17-8-4-2-5-9-17/h2-11,19H,12-16H2,1H3

> <INCHI_KEY>
VZSXTYKGYWISGQ-UHFFFAOYSA-N

> <FORMULA>
C19H24N2

> <MOLECULAR_WEIGHT>
280.415

> <EXACT_MASS>
280.193948781

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.15131424966427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-benzyl-1-methyl-N-phenylpiperidin-4-amine

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.8325689190000007

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.76024365713573

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
90.5503

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bamipine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -6.668  11.550   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      -6.668   6.930   0.000  0.00  0.00           N+0
CONECT    1   20                                                            
CONECT    2    4    5                                                       
CONECT    3    6    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   17                                                       
CONECT    9    5   17                                                       
CONECT   10    6   18                                                       
CONECT   11    7   18                                                       
CONECT   12   14   19                                                       
CONECT   13   15   19                                                       
CONECT   14   12   20                                                       
CONECT   15   13   20                                                       
CONECT   16   17   21                                                       
CONECT   17    8    9   16                                                  
CONECT   18   10   11   21                                                  
CONECT   19   12   13   21                                                  
CONECT   20    1   14   15                                                  
CONECT   21   16   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
Piperamine	ChEMBL
Bamipine	MeSH
Bamipine dihydrochloride	MeSH
Bamipine dihydrochloride, hydrate	MeSH
Bamipine monohydrochloride	MeSH
Bamipine citrate	MeSH
Bampine hydrochloride	MeSH
Bamipine lactate	MeSH
Soventol	MeSH
Bamipine ethanol hydrate	MeSH

Chemical Formula

C₁₉H₂₄N₂

Average Mass

280.4150 Da

Monoisotopic Mass

280.19395 Da

IUPAC Name

N-benzyl-1-methyl-N-phenylpiperidin-4-amine

Traditional Name

bamipine

CAS Registry Number

Not Available

SMILES

CN1CCC(CC1)N(CC1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H24N2/c1-20-14-12-19(13-15-20)21(18-10-6-3-7-11-18)16-17-8-4-2-5-9-17/h2-11,19H,12-16H2,1H3

InChI Key

VZSXTYKGYWISGQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Piper hispidum	LOTUS Database	35616633
Piper retrofractum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylbenzamines

Alternative Parents

Substituents

Phenylbenzamine
Benzylamine
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
4-aminopiperidine
Aralkylamine
Piperidine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Amine
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.96	ALOGPS
logP	3.83	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.55 m³·mol⁻¹	ChemAxon
Polarizability	33.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB13489

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bamipine

METLIN ID

Not Available

PubChem Compound

72075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for bamipine (NP0212031)

MOL for NP0212031 (bamipine)

3D MOL for NP0212031 (bamipine)

3D SDF for NP0212031 (bamipine)

3D-SDF for NP0212031 (bamipine)

PDB for NP0212031 (bamipine)

3D PDB for NP0212031 (bamipine)

SMILES for NP0212031 (bamipine)

INCHI for NP0212031 (bamipine)

Structure for NP0212031 (bamipine)

3D Structure for NP0212031 (bamipine)