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Showing NP-Card for mecamylamine (NP0242765)

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Record Information
Version2.0
Created at2022-09-07 03:09:22 UTC
Updated at2022-09-07 03:09:22 UTC
NP-MRD IDNP0242765
Secondary Accession NumbersNone
Natural Product Identification
Common Namemecamylamine
DescriptionMecamylamine, also known as versamine, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Mecamylamine is a drug which is used for the treatment of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. A comprehensive review of the pharmacology of mecamylamine was published in 2001. Mecamylamine is a very strong basic compound (based on its pKa). Mecamylamine is also sometimes used as an antiaddictive drug to help people stop smoking tobacco, and is now more widely used for this application than it is for lowering blood pressure. TC-5214 is currently in Phase III of clinical development as an add-on treatment and on stage II as a monotherapy treatment for major depression. Targacept voluntarily withdrew mecamylamine from the market in 2009 for reasons not related to safety or efficacy. Manchester Pharmaceuticals brought the drug back to market in 2013. mecamylamine is found in Wettsteinia inversa. In the United States, it was voluntarily withdrawn from the market in 2009 but was brought to market in 2013 as Vecamyl and eventually was marketed by Turing Pharmaceuticals.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0242765 (mecamylamine)

657
  Mrv0541 02231214522D          

 12 13  0  0  1  0            999 V2000
    2.5472   -1.1420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    0.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3065   -0.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440    0.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4701    0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491    1.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746    0.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    0.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3436   -0.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7845   -0.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2108   -1.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0242765 (mecamylamine)

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
    2.7813   -0.8280    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7352    0.1127    0.7873 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6532    0.0877   -0.1963 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2459    0.5163   -1.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1319   -1.3275   -0.2452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8376   -1.4097   -1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0992   -0.6930   -0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -0.0932    0.4023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8609   -1.3100    0.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243    0.8838    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3078    1.5503    1.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9101    1.9954   -0.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -1.2561   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7580   -0.2821    0.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8289   -1.6852    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4032   -0.1512    1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5616    1.0326   -2.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565   -0.4332   -2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    1.1830   -1.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -2.1064   -0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565   -0.9138   -2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0787   -2.4661   -1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954    0.0185   -1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920   -1.4341   -0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4486    0.2034    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3859   -1.1198    1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5092   -2.1897    0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439    0.8403    2.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558    2.1022    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731    2.2259    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075    1.6732   -1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7300    2.5588   -0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0893    2.7150   -0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 10  3  1  0
  9  5  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  4 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
M  END
Download

3D SDF for NP0242765 (mecamylamine)

657
  Mrv0541 02231214522D          

 12 13  0  0  1  0            999 V2000
    2.5472   -1.1420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    0.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3065   -0.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440    0.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4701    0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491    1.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8746    0.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    0.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3436   -0.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7845   -0.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2108   -1.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC1(C)C2CCC(C2)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3

> <INCHI_KEY>
IMYZQPCYWPFTAG-UHFFFAOYSA-N

> <FORMULA>
C11H21N

> <MOLECULAR_WEIGHT>
167.2911

> <EXACT_MASS>
167.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.74117247495387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
2.3736397596666663

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.875985632386264

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
51.832499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mecamylamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0242765 (mecamylamine)

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PDB for NP0242765 (mecamylamine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 657                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       4.755  -2.132   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.678   0.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.305  -0.961   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.802   1.504   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.478   0.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.878   2.736   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.099   0.552   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.775  -0.659   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.890   1.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.508  -0.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.331  -1.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.993  -2.328   0.000  0.00  0.00           C+0
CONECT    1    3   12                                                       
CONECT    2    3    4    9   10                                             
CONECT    3    1    2    5   11                                             
CONECT    4    2    6    7                                                  
CONECT    5    3    6    8                                                  
CONECT    6    4    5                                                       
CONECT    7    4    8                                                       
CONECT    8    5    7                                                       
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0242765 (mecamylamine)
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SMILES for NP0242765 (mecamylamine)
CNC1(C)C2CCC(C2)C1(C)C
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INCHI for NP0242765 (mecamylamine)
InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3
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View in JSmol
Synonyms
ValueSource
VersamineKegg
2-Methylamino-2,3,3-trimethylnorbornaneHMDB
2-MethylaminoisocamphaneHMDB
3-MethylaminoisocamphaneHMDB
MecamilaminaHMDB
Chemical FormulaC11H21N
Average Mass167.2911 Da
Monoisotopic Mass167.16740 Da
IUPAC NameN,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
Traditional Namemecamylamine
CAS Registry NumberNot Available
SMILES
CNC1(C)C2CCC(C2)C1(C)C
InChI Identifier
InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3
InChI KeyIMYZQPCYWPFTAG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Wettsteinia inversaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
    • 

  • Secondary amine
    • 

  • Secondary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.13ALOGPS
logP2.37ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)10.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.83 m³·mol⁻¹ChemAxon
Polarizability20.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014795  
DrugBank IDDB00657  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3892  
KEGG Compound IDC07511  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMecamylamine  
METLIN IDNot Available
PubChem Compound4032  
PDB IDNot Available
ChEBI ID100880  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]