Mecamylamine (CED0004463)

Record Information
Version1.0
Creation Date2016-05-22 03:42:55 UTC
Update Date2026-08-18 13:16:42 UTC
SynCED IDCED0004463
Secondary Accession Numbers
  • CHEM016761
Identification
Common NameMecamylamine
ClassSmall Molecule
Description
Mecamylamine is an organic compound with the chemical formula C11H21N and an average molecular weight of 167.29 g/mol. Mecamylamine belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. This compound is found in or released from 13 recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically antihypertensives. It is also associated with household cleaning and consumer products, including cigar cigarettes, non-electric simulated smoking devices, other smoking requisites, pipe accessories, and perfumes within detergents and soaps. Additionally, it is found in electrical and electronic equipment, such as antennas, conductors or conductive bodies characterised by the conductive materials, electrically stimulated smoking devices, electrodes, fixed capacitors and their manufacture, and one other source. The recorded route of exposure for this substance is oral. At the molecular level, mecamylamine interacts with four recorded protein targets. It functions as an antagonist of the neuronal acetylcholine receptor subunit alpha-2 (CHRNA2), neuronal acetylcholine receptor subunit alpha-7 (CHRNA7), neuronal acetylcholine receptor subunit alpha-4 (CHRNA4), and neuronal acetylcholine receptor subunit beta-2 (CHRNB2).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
VersamineKegg
2-methylamino-2,3,3-TrimethylnorbornaneHMDB
2-MethylaminoisocamphaneHMDB
3-MethylaminoisocamphaneHMDB
MecamilaminaHMDB
Chemical FormulaC11H21N
Average Molecular Mass167.291 g/mol
Monoisotopic Mass167.167 g/mol
CAS Registry Number60-40-2
IUPAC NameN,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
Traditional Namemecamylamine
SMILESCNC1(C)C2CCC(C2)C1(C)C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0zir-6900000000-b03c48241fa5a85462dbNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-d1e9fe76d5bc86bef4e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001r-9700000000-9505ece9327e31f47ce0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9000000000-e4663d1da4e4bc059200Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9000000000-c6fd00cf5fa5e7d227e5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-003r-9000000000-e197ecfa004b426aeb2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001r-9500000000-4e031bcaa41c1a77d136Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-02261581ecce2fe0aac6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-8ba64af50bf00f9a5e0cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01bi-9800000000-9dca2aa3f405803a3a06Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-e9b1b86ff3dc70c022c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-daf154fc054c52f0b366Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-5900000000-df288b2fc5172a2dd7b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-db62fc8b34c82c8f5c64Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066r-4900000000-874a6af6751c34126877Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05mo-9200000000-10eb0d95245c92b03fb3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-4c4edbe39675d0a24ee0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-4c4edbe39675d0a24ee0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-21bcf3029f6554b35934Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
515.0 Log mg/kg [290:920]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
CEDs000289Antihypertensives?Antihypertensives are a class of synthetic chemicals designed to manage high blood pressure and related cardiovascular conditions.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000506Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.Electrical & Electronic EquipmentNot Available
CEDs000511Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.Electrical & Electronic EquipmentNot Available
CEDs000518Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.Electrical & Electronic EquipmentNot Available
CEDs000519Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.Electrical & Electronic EquipmentNot Available
CEDs000521Fixed Capacitors And Their Manufacture?Fixed capacitors are passive electronic components used to store and release electrical energy, playing a critical role in various circuits.Electrical & Electronic EquipmentNot Available
CEDs000524Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.Electrical & Electronic EquipmentNot Available
CEDs000556Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.Household cleaning & consumer productsNot Available
CEDs000559Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.Household cleaning & consumer productsNot Available
CEDs000560Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.Household cleaning & consumer productsNot Available
CEDs000561Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.Household cleaning & consumer productsNot Available
CEDs000562Pipe Accessories?Pipe accessories, such as fittings, connectors, and seals, are components used in plumbing systems to facilitate the flow of liquids and gases.Household cleaning & consumer productsNot Available
CEDs000569Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.Household cleaning & consumer productsNot Available
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingNot Available
CEDs000592Marine Propulsion Or Steering?Marine propulsion and steering systems often rely on various synthetic chemicals, including lubricants, fuels, and hydraulic fluids.Marine, shipping & aquacultureNot Available
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsNot Available
CEDs000615Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.Personal care & cosmeticsNot Available
CEDs000632Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.Textiles, leather & furnishingsNot Available
CEDs000671Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.Aviation & AerospaceNot Available
CEDs000685Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.Building & ConstructionNot Available
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingNot Available
CEDs000703Blackboards?Blackboards, traditionally made from slate or coated wood, can also be produced using synthetic materials that may contain various chemicals.Paper, pulp & fiber productsNot Available
CEDs000739Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.Paper, pulp & fiber productsNot Available
CEDs000741Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.Paper, pulp & fiber productsNot Available
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsNot Available
Pathways
2 pathwaysPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Neuronal acetylcholine receptor subunit alpha-7 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P36544HumansPredicted (SEA)
Prediction Confidence Score
0.318
Applicability Domain
1.0
Statistical Significance
0.0071
Supporting Reference Compounds
77
E-value
55.4286
Acetylcholine receptor subunit alpha structureClick to view 3D structureAcetylcholine receptor subunit alphaP02710Torpedo californicaPredicted (SEA)
Prediction Confidence Score
0.286
Applicability Domain
1.0
Statistical Significance
4.00e-05
Supporting Reference Compounds
11
E-value
0.311397
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)
Prediction Confidence Score
0.193
Applicability Domain
0.22 Low confidence
Statistical Significance
0.1877
Supporting Reference Compounds
54
E-value
1460.92
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)
Prediction Confidence Score
0.182
Applicability Domain
0.22 Low confidence
Statistical Significance
0.0155
Supporting Reference Compounds
33
E-value
120.744
Serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform structureClick to view 3D structureSerine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoformQ76MZ3Mus musculusPredicted (SEA)
Prediction Confidence Score
0.176
Applicability Domain
0.176 Low confidence
Statistical Significance
4.70e-04
Supporting Reference Compounds
1
E-value
3.65891
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-4P28471Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.174
Applicability Domain
0.174 Low confidence
Statistical Significance
0.0027
Supporting Reference Compounds
1
E-value
20.8636
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)
Prediction Confidence Score
0.17
Applicability Domain
0.205 Low confidence
Statistical Significance
0.8929
Supporting Reference Compounds
266
E-value
6951.16
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)
Prediction Confidence Score
0.17
Applicability Domain
0.196 Low confidence
Statistical Significance
0.3221
Supporting Reference Compounds
49
E-value
2507.29
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)
Prediction Confidence Score
0.17
Applicability Domain
0.205 Low confidence
Statistical Significance
0.943
Supporting Reference Compounds
373
E-value
7341.34
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)
Prediction Confidence Score
0.17
Applicability Domain
0.205 Low confidence
Statistical Significance
0.9512
Supporting Reference Compounds
451
E-value
7405.17
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)
Prediction Confidence Score
0.169
Applicability Domain
0.205 Low confidence
Statistical Significance
0.908
Supporting Reference Compounds
297
E-value
7068.94
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)
Prediction Confidence Score
0.169
Applicability Domain
0.205 Low confidence
Statistical Significance
0.9596
Supporting Reference Compounds
506
E-value
7470.1
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)
Prediction Confidence Score
0.168
Applicability Domain
0.178 Low confidence
Statistical Significance
0.9582
Supporting Reference Compounds
562
E-value
7459.75
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)
Prediction Confidence Score
0.167
Applicability Domain
0.205 Low confidence
Statistical Significance
0.9933
Supporting Reference Compounds
1538
E-value
7733.07
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)
Prediction Confidence Score
0.165
Applicability Domain
0.191 Low confidence
Statistical Significance
0.0157
Supporting Reference Compounds
21
E-value
122.068
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)
Prediction Confidence Score
0.165
Applicability Domain
0.205 Low confidence
Statistical Significance
0.9599
Supporting Reference Compounds
385
E-value
7472.67
Click to view 3D structureOxytocin receptorP70536Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.164
Applicability Domain
0.206 Low confidence
Statistical Significance
0.3926
Supporting Reference Compounds
29
E-value
3056.52
Click to view 3D structureFarnesyltransferase, putativeQ4CXF7Trypanosoma cruzi (strain CL Brener)Predicted (SEA)
Prediction Confidence Score
0.163
Applicability Domain
0.163 Low confidence
Statistical Significance
0.0581
Supporting Reference Compounds
1
E-value
452.382
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)
Prediction Confidence Score
0.163
Applicability Domain
0.205 Low confidence
Statistical Significance
0.9591
Supporting Reference Compounds
386
E-value
7466.44
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)
Prediction Confidence Score
0.162
Applicability Domain
0.205 Low confidence
Statistical Significance
0.9735
Supporting Reference Compounds
487
E-value
7578.39
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)
Prediction Confidence Score
0.161
Applicability Domain
0.205 Low confidence
Statistical Significance
0.958
Supporting Reference Compounds
340
E-value
7458.03
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)
Prediction Confidence Score
0.161
Applicability Domain
0.205 Low confidence
Statistical Significance
0.9842
Supporting Reference Compounds
686
E-value
7661.84
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)
Prediction Confidence Score
0.16
Applicability Domain
0.205 Low confidence
Statistical Significance
0.984
Supporting Reference Compounds
823
E-value
7660.36
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)
Prediction Confidence Score
0.16
Applicability Domain
0.178 Low confidence
Statistical Significance
0.9939
Supporting Reference Compounds
1245
E-value
7737.43
Histamine H3 receptor structureClick to view 3D structureHistamine H3 receptorQ9Y5N1HumansPredicted (SEA)
Prediction Confidence Score
0.16
Applicability Domain
0.205 Low confidence
Statistical Significance
0.9543
Supporting Reference Compounds
294
E-value
7429.31
Concentrations
Not Available
External Links
DrugBank IDDB00657
HMDB IDHMDB0251089
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00015963
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMecamylamine
Chemspider ID3892
ChEBI IDNot Available
PubChem Compound ID4032
Kegg Compound IDC07511
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available