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Compound Detail

CHEMBL267936

MECAMYLAMINE
💊 Approved Drug
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💊 Approved Drug
CNC1(C)C2CCC(C2)C1(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267936
Name MECAMYLAMINE
Phase Approved
Structure Type MOL
InChI Key IMYZQPCYWPFTAG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Mecamilamina Mecamylamine
10
Targets
21
Activities
3
Assay Types
0
PK Parameters
20
Publications
2
Known Names
10
Indications

Molecular Properties

167.3
MW (Da)
2.42
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.63
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1956
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C11H21N
MW 167.30
Aromatic Rings 0
Heavy Atoms 12
NP-Likeness 1.56

Indications

Hypertension Alcoholism Depressive Disorder, Major Macular Degeneration Macular Degeneration Tobacco Use Disorder Aging Autistic Disorder Child Development Disorders, Pervasive Cognitive Dysfunction

ATC Classification

C02BB01
mecamylamine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: ANTIHYPERTENSIVES

Activity Summary

IC50 18 meas. best 7.0
EC50 2 meas. best 6.7
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 IC50 7.0 5.98 100.0 5
Neuronal acetylcholine receptor
CHEMBL2094110
 EC50 6.7 6.7 200.0 1
Neuronal acetylcholine receptor; alpha3/beta2
CHEMBL2109234
 IC50 6.55 6.55 280.0 1
Unchecked
CHEMBL612545
 IC50 6.52 5.785 300.0 2
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 IC50 6.22 6.22 600.0 1
Acetylcholine receptor subunit alpha
CHEMBL3097
 IC50 6.22 5.415 596.0 2
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 IC50 5.75 5.33 1800.0 2
Neuronal acetylcholine receptor; alpha2/beta4
CHEMBL2109230
 IC50 5.51 5.155 3100.0 2
Plasmodium falciparum
CHEMBL364
 IC50 5.22 4.63 6000.0 2
Muscle-type nicotinic acetylcholine receptor
CHEMBL2362997
 EC50 4.52 4.52 30000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 100.0 nM 7.0 Inhibitory activity against nicotinic acetylcholine receptor alpha3-beta4 15203153
Neuronal acetylcholine receptor EC50 = 200.0 nM 6.7 Compound was evaluated for functional potency and efficacy at rat Nicotinic acet... 9435889
Neuronal acetylcholine receptor; alpha3/beta2 IC50 = 280.0 nM 6.55 Inhibitory concentration against Nicotinic acetylcholine receptor alpha3-beta2 16033252
Unchecked IC50 = 300.0 nM 6.52 Antagonist activity at nAChR in Sprague-Dawley rat striatal slices assessed as i... 26164842
Acetylcholine receptor subunit alpha IC50 = 596.0 nM 6.22 Displacement of [3H]PCP from nAChR in Torpedo nobiliana electric organs membrane... -
Neuronal acetylcholine receptor; alpha4/beta2 IC50 = 600.0 nM 6.22 Antagonist activity at human alpha4beta2 nAChR expressed in HEK-tsA201 cells ass... 23757208
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 700.0 nM 6.16 Antagonist activity at human alpha3beta4 nAChR expressed in HEK-tsA201 cells ass... 23757208
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 1400.0 nM 5.85 Inhibitory concentration against Nicotinic acetylcholine receptor alpha3-beta4 16033252
Neuronal acetylcholine receptor subunit alpha-7 IC50 = 1800.0 nM 5.75 Ability to block activation of acetylcholine-stimulated currents in human alpha-... 9435889
Neuronal acetylcholine receptor; alpha2/beta4 IC50 = 3100.0 nM 5.51 Inhibitory concentration against Nicotinic acetylcholine receptor alpha2-beta4 16033252
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 3400.0 nM 5.47 Inhibitory concentration against Nicotinic acetylcholine receptor alpha3-beta4 16033252
Neuronal acetylcholine receptor; alpha3/beta4 IC50 = 3800.0 nM 5.42 Inhibitory concentration against Nicotinic acetylcholine receptor alpha3-beta4 16033252
Plasmodium falciparum IC50 = 6000.0 nM 5.22 Concentration required to reduce chloroquine IC50 by 50% 12109904
Unchecked IC50 = 8980.0 nM 5.05 Displacement of [3H]PCP from nAChR in Apis mellifera (honeybee0 head homogenates -
Neuronal acetylcholine receptor subunit alpha-7 IC50 = 12300.0 nM 4.91 Inhibitory concentration against Nicotinic acetylcholine receptor alpha 7 16033252
Neuronal acetylcholine receptor; alpha2/beta4 IC50 = 16000.0 nM 4.8 Inhibitory concentration against Nicotinic acetylcholine receptor alpha2-beta4 16033252
Acetylcholine receptor subunit alpha IC50 = 24700.0 nM 4.61 Displacement of [3H]PCP from nAChR in Torpedo nobiliana electric organs membrane... -
Muscle-type nicotinic acetylcholine receptor EC50 = 30000.0 nM 4.52 Compound was evaluated for functional potencies and efficacies at human muscle t... 9435889
Plasmodium falciparum IC50 = 91400.0 nM 4.04 In vitro inhibitory activity against multidrug-resistant Plasmodium falciparum W... 12109904

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
12109904 10.1021/jm011046l Plasmodium falciparum 4
- 10.1584/jpestics.20.49 Acetylcholine receptor subunit alpha 4
12109904 10.1021/jm011046l No relevant target 3
2002445 10.1021/jm00107a019 Mus musculus 3
2002445 10.1021/jm00107a019 No relevant target 3
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha3/beta4 3
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha4/beta4 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
22931300 10.1021/tx300075j Liver microsomes 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha2/beta4 2
- 10.1584/jpestics.20.57 Unchecked 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
4032427 10.1021/jm00147a021 Neuronal acetylcholine receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2

Data from ChEMBL 36 via Core Engine