Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 UTC
HMDB IDHMDB0014795
Secondary Accession Numbers
  • HMDB14795
Metabolite 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. Based on a literature review very few articles have been published on Mecamylamine.
Structure
Data?1582753221
Synonyms
ValueSource
VersamineKegg
2-methylamino-2,3,3-TrimethylnorbornaneHMDB
2-MethylaminoisocamphaneHMDB
3-MethylaminoisocamphaneHMDB
MecamilaminaHMDB
Chemical FormulaC11H21N
Average Molecular Weight167.2911
Monoisotopic Molecular Weight167.167399677
IUPAC NameN,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
Traditional Namemecamylamine
CAS Registry Number60-40-2
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/LNot Available
LogP2.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.17331661259
DarkChem[M-H]-135.99331661259
DeepCCS[M+H]+141.98530932474
DeepCCS[M-H]-139.21430932474
DeepCCS[M-2H]-175.28330932474
DeepCCS[M+Na]+150.75630932474
AllCCS[M+H]+137.332859911
AllCCS[M+H-H2O]+133.132859911
AllCCS[M+NH4]+141.132859911
AllCCS[M+Na]+142.232859911
AllCCS[M-H]-143.832859911
AllCCS[M+Na-2H]-145.032859911
AllCCS[M+HCOO]-146.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MecamylamineCNC1(C)C2CCC(C2)C1(C)C1415.1Standard polar33892256
MecamylamineCNC1(C)C2CCC(C2)C1(C)C1168.3Standard non polar33892256
MecamylamineCNC1(C)C2CCC(C2)C1(C)C1186.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mecamylamine,1TMS,isomer #1CN(C1(C)C2CCC(C2)C1(C)C)[Si](C)(C)C1354.4Semi standard non polar33892256
Mecamylamine,1TMS,isomer #1CN(C1(C)C2CCC(C2)C1(C)C)[Si](C)(C)C1427.5Standard non polar33892256
Mecamylamine,1TMS,isomer #1CN(C1(C)C2CCC(C2)C1(C)C)[Si](C)(C)C1449.7Standard polar33892256
Mecamylamine,1TBDMS,isomer #1CN(C1(C)C2CCC(C2)C1(C)C)[Si](C)(C)C(C)(C)C1591.6Semi standard non polar33892256
Mecamylamine,1TBDMS,isomer #1CN(C1(C)C2CCC(C2)C1(C)C)[Si](C)(C)C(C)(C)C1681.4Standard non polar33892256
Mecamylamine,1TBDMS,isomer #1CN(C1(C)C2CCC(C2)C1(C)C)[Si](C)(C)C(C)(C)C1611.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mecamylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zir-6900000000-b03c48241fa5a85462db2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mecamylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mecamylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mecamylamine LC-ESI-QQ , positive-QTOFsplash10-014i-0900000000-d1e9fe76d5bc86bef4e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mecamylamine LC-ESI-QQ , positive-QTOFsplash10-001r-9700000000-9505ece9327e31f47ce02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mecamylamine LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-e4663d1da4e4bc0592002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mecamylamine LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-c6fd00cf5fa5e7d227e52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mecamylamine LC-ESI-QQ , positive-QTOFsplash10-003r-9000000000-e197ecfa004b426aeb2b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mecamylamine LC-ESI-QTOF , positive-QTOFsplash10-001r-9500000000-4e031bcaa41c1a77d1362017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 10V, Positive-QTOFsplash10-014i-0900000000-02261581ecce2fe0aac62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 20V, Positive-QTOFsplash10-014i-0900000000-8ba64af50bf00f9a5e0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 40V, Positive-QTOFsplash10-01bi-9800000000-9dca2aa3f405803a3a062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 10V, Negative-QTOFsplash10-014i-0900000000-e9b1b86ff3dc70c022c82016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 20V, Negative-QTOFsplash10-014i-0900000000-daf154fc054c52f0b3662016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 40V, Negative-QTOFsplash10-0ue9-5900000000-df288b2fc5172a2dd7b02016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 10V, Positive-QTOFsplash10-014i-0900000000-db62fc8b34c82c8f5c642021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 20V, Positive-QTOFsplash10-066r-4900000000-874a6af6751c341268772021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 40V, Positive-QTOFsplash10-05mo-9200000000-10eb0d95245c92b03fb32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 10V, Negative-QTOFsplash10-014i-0900000000-4c4edbe39675d0a24ee02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 20V, Negative-QTOFsplash10-014i-0900000000-4c4edbe39675d0a24ee02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mecamylamine 40V, Negative-QTOFsplash10-014i-0900000000-21bcf3029f6554b359342021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00657 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00657 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00657
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00015963
Chemspider ID3892
KEGG Compound IDC07511
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMecamylamine
METLIN IDNot Available
PubChem Compound4032
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular weight:
59764.8
References
  1. 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 ]
  2. 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 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Struthers AM, Wilkinson JL, Dwoskin LP, Crooks PA, Bevins RA: Mecamylamine, dihydro-beta-erythroidine, and dextromethorphan block conditioned responding evoked by the conditional stimulus effects of nicotine. Pharmacol Biochem Behav. 2009 Dec;94(2):319-28. doi: 10.1016/j.pbb.2009.09.012. Epub 2009 Sep 22. [PubMed:19778551 ]
  5. Shytle RD, Penny E, Silver AA, Goldman J, Sanberg PR: Mecamylamine (Inversine): an old antihypertensive with new research directions. J Hum Hypertens. 2002 Jul;16(7):453-7. [PubMed:12080428 ]