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Mecamylamine

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Also known as MecamilaminaSID11111496SID26755706SID90341710SID104171190SID50111169SID144203749SID170465225(+/-)-Mecamylamine

Summary

Mecamylamine (CHEMBL267936) is an approved small molecule (ATC C02BB01) targeting CHRNA1, CHRNA2, and CHRNA3; indicated across 10 conditions including hypertensive disorder and age-related macular degeneration.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: C02BB01
  • Targets: 6 (CHRNA1, CHRNA2, CHRNA3…)
  • Indications: 10 conditions
  • Clinical trials: 17
  • Chemistry: 167.29 Da · C11H21N

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL267936
NameMecamylamine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID4032
ATCC02BB01
Molecular formulaC11H21N
Molecular weight167.29
InChIKeyIMYZQPCYWPFTAG-UHFFFAOYSA-N

SMILES: CC1(C2CCC(C2)C1(C)NC)C

IUPAC name: N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine

Also known as: Mecamilamina, Mecamylamine, SID11111496, SID26755706, SID90341710, SID104171190, SID50111169, mecamylamine, SID144203749, SID170465225, MECAMYLAMINE, (+/-)-Mecamylamine

Parent form; salt/anhydrous children: CHEMBL1237082

Patent coverage: 1,829 distinct patent families (5,623 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CHRNA1nicotinic acetylcholine receptor α1 subunit5.820%P02708
CHRNA2nicotinic acetylcholine receptor α2 subunit0.1%Q15822
CHRNA3nicotinic acetylcholine receptor α3 subunit5.120%P32297
CHRNA4nicotinic acetylcholine receptor α4 subunit5.440.2%P43681
CHRNA6nicotinic acetylcholine receptor α6 subunit4.960.1%Q15825
CHRNA7nicotinic acetylcholine receptor α7 subunit4.810.1%P36544

Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: Pyruvate kinase PKM, Prelamin-A/C, Thrombopoietin, Neuronal acetylcholine receptor; alpha4/beta2, Neuronal acetylcholine receptor; alpha3/beta4, Neuronal acetylcholine receptor, Neuronal acetylcholine receptor; alpha2/beta4, Neuronal acetylcholine receptor; alpha3/beta2, Muscle-type nicotinic acetylcholine receptor, Neuronal acetylcholine receptor subunit alpha-7.

Bioactivity

ChEMBL activities: 18 potent at pChembl ≥ 5 of 27 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
PKM8Potency10nMCHEMBL_ACT_4388242
PKM8Potency10nMCHEMBL_ACT_4583905
CHRNB47IC50100nMCHEMBL_ACT_1040440
P047576.7EC50200nMCHEMBL_ACT_95884
CHRNB26.55IC50280nMCHEMBL_ACT_1484920
P027106.22IC50596nMCHEMBL_ACT_12574646
CHRNB26.22IC50600nMCHEMBL_ACT_13390152
CHRNB46.16IC50700nMCHEMBL_ACT_13390124
CHRNB45.85IC501400nMCHEMBL_ACT_1484927
CHRNA75.75IC501800nMCHEMBL_ACT_95885
CHRNB45.68IC502100nMCHEMBL_ACT_29203267
CHRNB45.51IC503100nMCHEMBL_ACT_1484925
NFKB15.5Potency3162nMCHEMBL_ACT_3672684
NFKB15.5Potency3162nMCHEMBL_ACT_4585965
CHRNB45.47IC503400nMCHEMBL_ACT_1484929
CHRNB45.42IC503800nMCHEMBL_ACT_1484928
THPO5Potency10000nMCHEMBL_ACT_4809560
THPO5Potency10000nMCHEMBL_ACT_5074267

Target pathways

Aggregated over 6 target gene(s): CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6, CHRNA7.

Top Reactome pathways

9 total, by targets touching each:

PathwayTargetsGenes
Neurotransmitter receptors and postsynaptic signal transmission6CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6, CHRNA7
Transmission across Chemical Synapses6CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6, CHRNA7
Neuronal System6CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6, CHRNA7
Acetylcholine binding and downstream events6CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6, CHRNA7
Postsynaptic nicotinic acetylcholine receptors6CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6, CHRNA7
Highly calcium permeable postsynaptic nicotinic acetylcholine receptors6CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6, CHRNA7
Presynaptic nicotinic acetylcholine receptors5CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6
Highly calcium permeable nicotinic acetylcholine receptors5CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6
Highly sodium permeable postsynaptic acetylcholine nicotinic receptors2CHRNA3, CHRNA4

Dominant GO biological processes

GO termTargets
synaptic transmission, cholinergic6
monoatomic ion transmembrane transport6
response to nicotine6
acetylcholine receptor signaling pathway6
monoatomic ion transport6
excitatory postsynaptic potential6
neuromuscular synaptic transmission5
membrane depolarization5
presynaptic modulation of chemical synaptic transmission5
regulation of postsynaptic membrane potential5
signal transduction5
regulation of membrane potential4
response to acetylcholine3
behavioral response to nicotine3
chemical synaptic transmission3

Indications & clinical

Indications

10 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
hypertensive disorder4MONDO:0005044EFO:0000537
age-related macular degeneration2MONDO:0005150EFO:0001365
nicotine dependence2MONDO:0008575EFO:0003768
macular degeneration2MONDO:0003004EFO:0009606
major depressive disorder2MONDO:0002009MONDO:0002009
alcohol abuse2MONDO:0002046MONDO:0007079
autism1MONDO:0005260EFO:0003758
pervasive developmental disorder1MONDO:0000594MONDO:0000594

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 17.

Phase distribution

PhaseTrials
PHASE26
PHASE13
Not specified3
EARLY_PHASE12
PHASE41
PHASE31
PHASE1/PHASE21

Top trials by phase / activity

NCTPhaseStatusTitle
NCT03914677PHASE4UNKNOWNMecamylamine for Autonomic Dysreflexia Prophylaxis
NCT00563797PHASE3COMPLETEDMecamylamine for the Treatment of Patients With Depression and Alcohol Dependence
NCT00262470PHASE1/PHASE2ACTIVE_NOT_RECRUITINGTreatment of Orthostatic Intolerance
NCT00018161PHASE2COMPLETEDTreatment to Quit Smoking
NCT00319319PHASE2COMPLETEDNicotinic Receptor Augmentation of SSRI Antidepressants
NCT00342563PHASE2COMPLETEDTreatment With Mecamylamine in Smoking and Non-smoking Alcohol Dependent Patients
NCT00414206PHASE2TERMINATEDSafety and Efficacy of ATG003 in Patients With Wet Age-Related Macular Degeneration (AMD)
NCT00536692PHASE2COMPLETEDTopical Ocular Mecamylamine in Diabetic Macular Edema (DME)
NCT00593879PHASE2COMPLETEDFlexible Dose Titration Add-on Study to Treat Major Depressive Disorder
NCT00018187PHASE1COMPLETEDCombinations of Pharmacologic Smoking Cessation Treatments
NCT00773812PHASE1COMPLETEDPlacebo-Controlled Pilot Trial of Mecamylamine for Treatment of Autism Spectrum Disorders
NCT03408574PHASE1COMPLETEDThe Nicotinic Cholinergic System and Cognitive Aging
NCT06002477EARLY_PHASE1RECRUITINGAttentional Mechanisms in SCD
NCT04756232EARLY_PHASE1COMPLETEDCholinergic Mechanisms of Attention in Aging
NCT00455650Not specifiedCOMPLETEDStudy of the Effects of Mecamylamine and Varenicline in Schizophrenia
NCT01223404Not specifiedCOMPLETEDNicotinic Modulation of the Default Network
NCT03244488Not specifiedCOMPLETEDMental Ability Challenge Study in Adults With and Without HIV

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

144 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
NICOTINEChEMBL + PubChemPhase 4 (approved)CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA6, CHRNA7
VARENICLINEChEMBL + PubChemPhase 4 (approved)CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA7
CYTISINICLINEChEMBL + PubChemPhase 3 (approved)CHRNA1, CHRNA2, CHRNA3, CHRNA4, CHRNA7
BUPROPIONChEMBL + PubChemPhase 4 (approved)CHRNA1, CHRNA3, CHRNA4, CHRNA7
TROPISETRONChEMBLPhase 4 (approved)CHRNA1, CHRNA3, CHRNA4, CHRNA7
DEXMECAMYLAMINEChEMBLPhase 3CHRNA1, CHRNA3, CHRNA4, CHRNA7
ALTINICLINEChEMBLPhase 2CHRNA1, CHRNA2, CHRNA3, CHRNA4
GTS-21ChEMBLPhase 2CHRNA1, CHRNA3, CHRNA4, CHRNA7
ACETYLCHOLINEChEMBL + PubChemPhase 4 (approved)CHRNA3, CHRNA4, CHRNA7
OndansetronChEMBL + PubChemPhase 4 (approved)CHRNA1, CHRNA3, CHRNA4
AZD1446ChEMBLPhase 2CHRNA3, CHRNA4, CHRNA7
RADAFAXINEChEMBLPhase 2CHRNA1, CHRNA3, CHRNA4
RIVANICLINEChEMBLPhase 2CHRNA3, CHRNA4, CHRNA7
STILONIUM IODIDEChEMBLPhase 2CHRNA3, CHRNA4, CHRNA7
TEBANICLINEChEMBLPhase 2CHRNA3, CHRNA4, CHRNA7
AtracuriumChEMBL + PubChemPhase 4 (approved)CHRNA1, CHRNA4
CARBAMOYLCHOLINEChEMBLPhase 4 (approved)CHRNA4, CHRNA7
GRANISETRONChEMBLPhase 4 (approved)CHRNA3, CHRNA4
AZD0328ChEMBLPhase 2CHRNA4, CHRNA7
BRADANICLINEChEMBLPhase 2CHRNA4, CHRNA7
LOBELINEChEMBLPhase 2CHRNA4, CHRNA7
SOFINICLINEChEMBLPhase 2CHRNA3, CHRNA4
CinacalcetPubChemApprovedCHRNA4, CHRNA7
PemigatinibPubChemApprovedCHRNA2, CHRNA6
SulindacPubChemApprovedCHRNA4, CHRNA7
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)CHRNA4
RIFAMPINChEMBL + PubChemPhase 4 (approved)CHRNA4
ANISOTROPINEChEMBLPhase 4 (approved)CHRNA4
AZELASTINEChEMBLPhase 4 (approved)CHRNA4
CHLOROPROCAINEChEMBLPhase 4 (approved)CHRNA4
CHLORPHENTERMINEChEMBLPhase 4 (approved)CHRNA4
DAUNORUBICINChEMBLPhase 4 (approved)CHRNA4
DIPHEMANILChEMBLPhase 4 (approved)CHRNA4
EPALRESTATChEMBLPhase 4 (approved)CHRNA4
FENTANYLChEMBLPhase 4 (approved)CHRNA4
ILOPERIDONEChEMBLPhase 4 (approved)CHRNA4
MEDAZEPAMChEMBLPhase 4 (approved)CHRNA4
MOXISYLYTEChEMBLPhase 4 (approved)CHRNA4
NALTREXONEChEMBLPhase 4 (approved)CHRNA7
NIMESULIDEChEMBLPhase 4 (approved)CHRNA4
NITAZOXANIDEChEMBLPhase 4 (approved)CHRNA4
OXYPERTINEChEMBLPhase 4 (approved)CHRNA4
PALBOCICLIBChEMBLPhase 4 (approved)CHRNA4
PALONOSETRONChEMBLPhase 4 (approved)CHRNA4
PONATINIBChEMBLPhase 4 (approved)CHRNA4
PYRVINIUMChEMBLPhase 4 (approved)CHRNA4
RIFAXIMINChEMBLPhase 4 (approved)CHRNA4
SERTINDOLEChEMBLPhase 4 (approved)CHRNA4
SUNITINIBChEMBLPhase 4 (approved)CHRNA4
THIORIDAZINEChEMBLPhase 4 (approved)CHRNA4
VANDETANIBChEMBLPhase 4 (approved)CHRNA4
ZIMELDINEChEMBLPhase 4 (approved)CHRNA4
CINITAPRIDEChEMBLPhase 3CHRNA4
DIACEREINChEMBLPhase 3CHRNA4
ENCENICLINEChEMBLPhase 3CHRNA7
PYRONARIDINEChEMBLPhase 3CHRNA4
RADOTINIBChEMBLPhase 3CHRNA4
TRIMEBUTINEChEMBLPhase 3CHRNA4
18-METHOXYCORONARIDINEChEMBLPhase 2CHRNA3
ALCURONIUMChEMBLPhase 2CHRNA4

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot