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Compound Detail

CHEMBL376897

METHSCOPOLAMINE
💊 Approved Drug
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💊 Approved Drug
C[N+]1(C)[C@@H]2C[C@@H](OC(=O)[C@H](CO)c3ccccc3)C[C@H]1[C@@H]1O[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL376897
Name METHSCOPOLAMINE
Phase Approved
Structure Type MOL
InChI Key LZCOQTDXKCNBEE-IKIFYQGPSA-N
Therapeutic ✓ Yes

Known Names

(-)-n-methylscopolamine Methscopolamine cation Methscopolamine ion Methylscopolamine N-methylhyoscine N-methylscopolamine
9
Targets
43
Activities
4
Assay Types
0
PK Parameters
20
Publications
6
Known Names
1
Indications

Molecular Properties

318.4
MW (Da)
1.06
ALogP
4
HBA
1
HBD
59.1
PSA (Ų)
0.51
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1953
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C18H24NO4+
MW 318.39
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 1.14

Indications

Digestive System Diseases

ATC Classification

A03BB03
methylscopolamine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
S01FA03
methylscopolamine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 27 meas. best 10.2
IC50 8 meas. best 8.96
Kd 6 meas. best 9.33
EC50 2 meas. best 10.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M3
CHEMBL320
 EC50 10.3 10.005 0.1 2
Muscarinic acetylcholine receptor M2
CHEMBL211
 Ki 10.2 9.37 0.1 10
Muscarinic acetylcholine receptor M1
CHEMBL216
 Ki 10.02 9.652 0.1 5
Muscarinic acetylcholine receptor M3
CHEMBL245
 Ki 9.87 9.87 0.1 3
Muscarinic acetylcholine receptor M4
CHEMBL1821
 Ki 9.85 9.85 0.1 3
Muscarinic acetylcholine receptor M5
CHEMBL2035
 Ki 9.68 9.4975 0.2 4
Muscarinic receptor 2
CHEMBL1075061
 Kd 9.33 9.33 0.5 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 Kd 9.33 9.33 0.5 1
Muscarinic acetylcholine receptor M3
CHEMBL5498
 Kd 9.21 9.21 0.6 2
Muscarinic acetylcholine receptor M3
CHEMBL245
 IC50 8.96 8.96 1.1 1
Muscarinic acetylcholine receptor M1
CHEMBL216
 IC50 8.74 8.74 1.8 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
 IC50 8.64 8.64 2.3 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
 IC50 8.64 8.64 2.3 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 IC50 8.37 6.8575 4.3 4
Muscarinic receptor 4
CHEMBL1075071
 Kd 8.19 8.19 6.5 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
 Kd 8.19 8.19 6.5 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M3 EC50 = 0.05 nM 10.3 Stimulation of disulfide bond cross-linking formation in rat M3'(3C)-Xa receptor... 17623649
Muscarinic acetylcholine receptor M2 Ki = 0.0631 nM 10.2 Displacement of [3H]UNSW-MK259 from human muscarinic acetylcholine receptor M2 e... 28388054
Muscarinic acetylcholine receptor M1 Ki = 0.0955 nM 10.02 Displacement of [3H]NMS from EGFP-fused human M1 receptor N-terminal truncated a... 22329602
Muscarinic acetylcholine receptor M3 Ki = 0.1349 nM 9.87 Displacement of [3H]N-methylscopolamine from human muscarinic M3 receptor expres... 22243489
Muscarinic acetylcholine receptor M3 Ki = 0.1349 nM 9.87 Displacement of [3H]NMS from human cloned muscarinic M3 receptor expressed in CH... 19928767
Muscarinic acetylcholine receptor M3 Ki = 0.1349 nM 9.87 Binding affinity to human cloned muscarinic receptor M3 expressed in CHO cells 17305327
Muscarinic acetylcholine receptor M4 Ki = 0.1413 nM 9.85 Displacement of [3H]N-methylscopolamine from human muscarinic M4 receptor expres... 22243489
Muscarinic acetylcholine receptor M4 Ki = 0.1413 nM 9.85 Displacement of [3H]NMS from human cloned muscarinic M4 receptor expressed in CH... 19928767
Muscarinic acetylcholine receptor M4 Ki = 0.1413 nM 9.85 Binding affinity to human cloned muscarinic receptor M4 expressed in CHO cells 17305327
Muscarinic acetylcholine receptor M1 Ki = 0.1698 nM 9.77 Competitive inhibition of EGFP-fused human M1 receptor N-terminal truncated at 1... 22329602
Muscarinic acetylcholine receptor M2 Ki = 0.1778 nM 9.75 Displacement of [3H]N-methylscopolamine from human muscarinic M2 receptor expres... 22243489
Muscarinic acetylcholine receptor M2 Ki = 0.1778 nM 9.75 Displacement of [3H]NMS from human cloned muscarinic M2 receptor expressed in CH... 19928767
Muscarinic acetylcholine receptor M2 Ki = 0.1778 nM 9.75 Binding affinity to human cloned muscarinic receptor M2 expressed in CHO cells 17305327
Muscarinic acetylcholine receptor M3 EC50 = 0.195 nM 9.71 Stimulation of disulfide bond cross-linking formation in rat M3'(3C)-Xa receptor... 17623649
Muscarinic acetylcholine receptor M5 Ki = 0.2089 nM 9.68 Displacement of [3H]N-methylscopolamine from human muscarinic M5 receptor expres... 22243489
Muscarinic acetylcholine receptor M5 Ki = 0.2089 nM 9.68 Displacement of [3H]NMS from human cloned muscarinic M5 receptor expressed in CH... 19928767
Muscarinic acetylcholine receptor M5 Ki = 0.2089 nM 9.68 Binding affinity to human cloned muscarinic receptor M5 expressed in CHO cells 17305327
Muscarinic acetylcholine receptor M1 Ki = 0.3236 nM 9.49 Binding affinity to human cloned muscarinic receptor M1 expressed in CHO cells 17305327
Muscarinic acetylcholine receptor M1 Ki = 0.3236 nM 9.49 Displacement of [3H]NMS from human cloned muscarinic M1 receptor expressed in CH... 19928767
Muscarinic acetylcholine receptor M1 Ki = 0.3236 nM 9.49 Displacement of [3H]N-methylscopolamine from human muscarinic M1 receptor expres... 22243489

Literature References

PubMed DOI Target Context # Activities
17623649 10.1074/jbc.m704875200 Muscarinic acetylcholine receptor M3 10
28388054 10.1021/acs.jmedchem.6b01892 Muscarinic acetylcholine receptor M2 5
25051097 10.1021/jm500790x Muscarinic acetylcholine receptor M2 5
17305327 10.1021/jm061374r Muscarinic acetylcholine receptor M3 2
22705021 10.1016/j.bmc.2012.05.042 Unchecked 2
22329602 10.1021/jm201348t Muscarinic acetylcholine receptor M1 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
19928767 10.1021/jm901048j Muscarinic acetylcholine receptor M3 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
17305327 10.1021/jm061374r Muscarinic acetylcholine receptor M4 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
17305327 10.1021/jm061374r Muscarinic acetylcholine receptor M2 2
17305327 10.1021/jm061374r Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
17305327 10.1021/jm061374r Muscarinic acetylcholine receptor M5 1
14695827 10.1021/jm030351z Monoclonal antibody (mAb) 2E2 1
9703467 10.1021/jm9708588 Muscarinic acetylcholine receptor M2 1
9873472 10.1016/s0960-894x(98)00351-5 Muscarinic acetylcholine receptor M5 1

Data from ChEMBL 36 via Core Engine