(2-Carbamoyloxy-ethyl)-trimethyl-ammonium chloride

ID: ALA14

Chembl Id: CHEMBL14

Cas Number: 51-83-2

PubChem CID: 5831

Product Number: C133466

Max Phase: Approved

First Approval: 1972

Molecular Formula: C6H15ClN2O2

Molecular Weight: 147.20

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Carbachol | Carbachol chloride | Carbacholine Chloride | Carbamoylcholine chloride | NSC-32865 | carbachol|51-83-2|Carbamoylcholine chloride|Carbamylcholine chloride|Miostat|CARBACHOL CHLORIDE|Jestryl|Carbastat|Carbacholine chloride|Carbacholin|Carbacolina|Carbamiotin|Carbocholine|Carcholin|Vasoperif|Coletyl|Lentin|Doryl|Moryl|Isopto Carbachol|Choline carbamate chloride|Carbacholum|Carbocholin|Carbochol|Carbyl|Carbacholine|Choline chloride, carbamate|Carbaminocholine chloride|Carbacol|Karbachol|Show More

Trade Names(4): Carbachol | Carbastat | Doryl | Miostat

Canonical SMILES:  C[N+](C)(C)CCOC(N)=O.[Cl-]

Standard InChI:  InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H

Standard InChI Key:  AIXAANGOTKPUOY-UHFFFAOYSA-N

Associated Targets(Human)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM4 Tclin Muscarinic acetylcholine receptor M4 (6041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM3 Tclin Muscarinic acetylcholine receptor (1128 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM3 Tclin Muscarinic acetylcholine receptors; M2 & M3 (708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EDNRA Tclin Endothelin receptor ET-A (5008 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptors; M1 & M2 (498 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-N-SH (1499 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1/M5 chimeric protein (31 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RY2 Tclin Purinergic receptor P2Y2 (1109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BLM Tchem Bloom syndrome protein (4248 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CALM1 Tclin Calmodulin (82 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD4 Tchem Dopamine D4 receptor (7907 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR2 Tclin Estrogen receptor beta (9272 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH1 Tclin Histamine H1 receptor (7573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH2 Tclin Histamine H2 receptor (5428 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HMGCR Tclin HMG-CoA reductase (2475 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYSLTR1 Tclin Cysteinyl leukotriene receptor 1 (2118 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC3R Tchem Melanocortin receptor 3 (5659 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC4R Tclin Melanocortin receptor 4 (10016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC5R Tchem Melanocortin receptor 5 (4283 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPY1R Tchem Neuropeptide Y receptor type 1 (5019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPY2R Tchem Neuropeptide Y receptor type 2 (3731 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRD1 Tclin Delta opioid receptor (15096 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Tclin Kappa opioid receptor (16155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE5A Tclin Phosphodiesterase 5A (5113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTAFR Tchem Platelet activating factor receptor (2575 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP1 Tchem Caspase-1 (6235 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CTSG Tchem Cathepsin G (2304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ELANE Tclin Leukocyte elastase (8173 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP9 Tchem Matrix metalloproteinase 9 (6779 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCA Tchem Protein kinase C alpha (5923 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK3 Tchem MAP kinase ERK1 (4725 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK1 Tchem MAP kinase ERK2 (25055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPP3CA Tchem Serine/threonine protein phosphatase 2B catalytic subunit, alpha isoform (1831 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FYN Tclin Tyrosine-protein kinase FYN (5308 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPRC Tchem Leukocyte common antigen (2317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR6 Tchem Serotonin 6 (5-HT6) receptor (9749 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Tclin Sigma opioid receptor (6358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TACR1 Tclin Neurokinin 1 receptor (6273 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TACR2 Tchem Neurokinin 2 receptor (3341 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TBXAS1 Tchem Thromboxane-A synthase (3355 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FLT1 Tclin Vascular endothelial growth factor receptor 1 (6262 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VIPR1 Tchem Vasoactive intestinal polypeptide receptor 1 (1904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB3 Tclin Beta-3 adrenergic receptor (5850 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR2 Tchem Angiotensin II type 2 (AT-2) receptor (2549 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CALCR Tclin Calcitonin receptor (2215 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR2 Tchem C-C chemokine receptor type 2 (5628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR4 Tclin C-C chemokine receptor type 4 (2819 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR5 Tclin C-C chemokine receptor type 5 (5640 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CXCR1 Tchem Interleukin-8 receptor A (2256 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CXCR2 Tchem Interleukin-8 receptor B (3491 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCKAR Tclin Cholecystokinin A receptor (4460 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2E1 Tchem Cytochrome P450 2E1 (2174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD2 Tclin Dopamine D2 receptor (23596 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GALC Tbio Galactocerebrosidase (1984 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GPR146 Tbio Probable G-protein coupled receptor 146 (24 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

GPM3 Muscarinic acetylcholine receptor M3 (1154 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor M1 (3437 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor (3770 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cavia porcellus (23802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor M1 (123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm2 Muscarinic acetylcholine receptor M2 (85 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm3 Muscarinic acetylcholine receptor M3 (70 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A9 (98 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna2 Neuronal acetylcholine receptor; alpha2/beta2 (198 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna3 Neuronal acetylcholine receptor; alpha3/beta2 (421 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna3 Neuronal acetylcholine receptor; alpha3/beta4 (1368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna4 Neuronal acetylcholine receptor; alpha4/beta2 (3557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna4 Neuronal acetylcholine receptor; alpha4/beta4 (595 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna3 Neuronal acetylcholine receptor (756 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm2 Muscarinic acetylcholine receptor M2 (1011 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic receptor M1 and M2 (189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oryctolagus cuniculus (11301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Arpp19 cyclic AMP phosphoprotein (35 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm3 Muscarinic acetylcholine receptor M3 (655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm4 Muscarinic acetylcholine receptor M4 (559 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ache Acetylcholinesterase (1323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
chrnd Acetylcholine receptor protein delta chain (49 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aorta (2975 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ampC Beta-lactamase AmpC (62480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Glra2 Glycine receptor (1745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Insr Insulin receptor (1750 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LTC4S Leukotriene C4 synthase (1746 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15 Arachidonate 15-lipoxygenase (2064 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos1 Nitric-oxide synthase, brain (2987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos2 Nitric oxide synthase, inducible (3573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Progesterone receptor (1742 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACE Angiotensin-converting enzyme (2863 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr1a Serotonin 1a (5-HT1a) receptor (8655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr1b Serotonin 1b (5-HT1b) receptor (2343 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR4 Serotonin 4 (5-HT4) receptor (2870 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ar Androgen Receptor (5522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1a Alpha-1a adrenergic receptor (3346 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1b Alpha-1b adrenergic receptor (2470 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Akr1b1 Aldose reductase (4007 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
nAChRalpha5 Nicotinic acetylcholine receptor alpha 5 subunit (134 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA1 Acetylcholine receptor protein alpha chain (109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: Yes
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: YesProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 147.20Molecular Weight (Monoisotopic): 147.1128AlogP: -0.21#Rotatable Bonds: 3
Polar Surface Area: 52.32Molecular Species: NEUTRALHBA: 2HBD: 1
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: -4.55CX LogD: -4.55
Aromatic Rings: Heavy Atoms: 10QED Weighted: 0.56Np Likeness Score: 1.00

References

1. Sauerberg P, Larsen JJ, Falch E, Krogsgaard-Larsen P..  (1986)  A novel class of conformationally restricted heterocyclic muscarinic agonists.,  29  (6): [PMID:3712371] [10.1021/jm00156a018]
2. Bradbury BJ, Baumgold J, Paek R, Kammula U, Zimmet J, Jacobson KA..  (1991)  Muscarinic receptor binding and activation of second messengers by substituted N-methyl-N-[4-(1-azacycloalkyl)-2-butynyl]acetamides.,  34  (3): [PMID:1848294] [10.1021/jm00107a029]
3. Showell GA, Gibbons TL, Kneen CO, MacLeod AM, Merchant K, Saunders J, Freedman SB, Patel S, Baker R..  (1991)  Tetrahydropyridyloxadiazoles: semirigid muscarinic ligands.,  34  (3): [PMID:2002451] [10.1021/jm00107a032]
4. Sowell JW, Tang Y, Valli MJ, Chapman JM, Usher LA, Vaughan CM, Kosh JW..  (1992)  Synthesis and cholinergic properties of bis[[(dimethylamino)methyl]furanyl] analogues of ranitidine.,  35  (6): [PMID:1552502] [10.1021/jm00084a015]
5. Saunders J, Cassidy M, Freedman SB, Harley EA, Iversen LL, Kneen C, MacLeod AM, Merchant KJ, Snow RJ, Baker R..  (1990)  Novel quinuclidine-based ligands for the muscarinic cholinergic receptor.,  33  (4): [PMID:2319559] [10.1021/jm00166a008]
6. Stähle H, Daniel H, Kobinger W, Lillie C, Pichler L..  (1980)  Chemistry, pharmacology, and structure-activity relationships with a new type of imidazolines exerting a specific bradycardic action at a cardiac site.,  23  (11): [PMID:7452671] [10.1021/jm00185a013]
7. Messer WS, Abuh YF, Liu Y, Periyasamy S, Ngur DO, Edgar MA, El-Assadi AA, Sbeih S, Dunbar PG, Roknich S, Rho T, Fang Z, Ojo B, Zhang H, Huzl JJ, Nagy PI..  (1997)  Synthesis and biological characterization of 1,4,5,6-tetrahydropyrimidine and 2-amino-3,4,5,6-tetrahydropyridine derivatives as selective m1 agonists.,  40  (8): [PMID:9111297] [10.1021/jm960467d]
8. Sloan JW, Martin WR, Hook R, Hernandez J..  (1985)  Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.,  28  (9): [PMID:4032427] [10.1021/jm00147a021]
9. Koskinen AM, Rapoport H..  (1985)  Synthetic and conformational studies on anatoxin-a: a potent acetylcholine agonist.,  28  (9): [PMID:4032432] [10.1021/jm00147a032]
10. Hobbs SH, Johnson SJ, Kesten SR, Pavia MR, Davis RE, Schwarz RD, Coughenour LL, Myers SL, Dudley DT, Moss WH.  (1991)  Cholinergic agents: 2-oxazolidinone analogues of the acetylcholine-receptor muscarinic agonist pilocarpine,  (3): [10.1016/S0960-894X(01)80787-3]
11. Nordvall G, Sundquist S, Glas G, Gogoll A, Nilvebrant L, Hacksell U..  (1992)  Analogues of the muscarinic agent 2'-methylspiro[1-azabicyclo[2.2.2]octane-3,4'-[1,3]dioxolane]: synthesis and pharmacology.,  35  (9): [PMID:1578479] [10.1021/jm00087a007]
12. Teodori E, Gualtieri F, Angeli P, Brasili L, Giannella M, Pigini M..  (1986)  Resolution, absolute configuration, and cholinergic enantioselectivity of (+)- and (-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide.,  29  (9): [PMID:3746812] [10.1021/jm00159a009]
13. Ringdahl B, Roch M, Jenden DJ..  (1988)  Tertiary 3- and 4-haloalkylamine analogues of oxotremorine as prodrugs of potent muscarinic agonists.,  31  (1): [PMID:3336014] [10.1021/jm00396a024]
14. Andrews PR, Craik DJ, Martin JL..  (1984)  Functional group contributions to drug-receptor interactions.,  27  (12): [PMID:6094812] [10.1021/jm00378a021]
15. Ringdahl B..  (1988)  Dimethylsulfonium and thiolanium analogues of the muscarinic agent oxotremorine.,  31  (1): [PMID:3336015] [10.1021/jm00396a025]
16. Xiao Y, Baydyuk M, Wang HP, Davis HE, Kellar KJ..  (2004)  Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.,  14  (8): [PMID:15050613] [10.1016/j.bmcl.2003.09.105]
17. Teodori E, Gualtieri F, Angeli P, Brasili L, Giannella M..  (1987)  Resolution, absolute configuration, and cholinergic enantioselectivity of (-)- and (+)-c-2-methyl-r-5-[(dimethylamino)methyl]-1,3-oxathiolane t-3-oxide methiodide and related sulfones.,  30  (10): [PMID:3656366] [10.1021/jm00393a042]
18. Augelli-Szafran CE, Jaen JC, Moreland DW, Nelson CB, Penvose-Yi JR, Schwarz RD..  (1998)  Identification and characterization of m4 selective muscarinic antagonists.,  (15): [PMID:9873472] [10.1016/s0960-894x(98)00351-5]
19. Jeppesen L, Olesen PH, Hansen L, Sheardown MJ, Thomsen C, Rasmussen T, Jensen AF, Christensen MS, Rimvall K, Ward JS, Whitesitt C, Calligaro DO, Bymaster FP, Delapp NW, Felder CC, Shannon HE, Sauerberg P..  (1999)  1-(1,2,5-Thiadiazol-4-yl)-4-azatricyclo[2.2.1.0(2,6)]heptanes as new potent muscarinic M1 agonists: structure-activity relationship for 3-aryl-2-propyn-1-yloxy and 3-aryl-2-propyn-1-ylthio derivatives.,  42  (11): [PMID:10354408] [10.1021/jm9910019]
20. Pei XF, Gupta TH, Badio B, Padgett WL, Daly JW..  (1998)  6beta-Acetoxynortropane: a potent muscarinic agonist with apparent selectivity toward M2-receptors.,  41  (12): [PMID:9622546] [10.1021/jm9705115]
21. Pei XF, Gupta TH, Badio B, Padgett WL, Daly JW..  (1998)  6beta-Acetoxynortropane: a potent muscarinic agonist with apparent selectivity toward M2-receptors.,  41  (12): [PMID:9622546] [10.1021/jm9705115]
22. MacLeod AM, Baker R, Freedman SB, Patel S, Merchant KJ, Roe M, Saunders J..  (1990)  Synthesis and muscarinic activities of 1,2,4-thiadiazoles.,  33  (7): [PMID:2362286] [10.1021/jm00169a041]
23. Carroll FI, Abraham P, Chemburkar S, He XC, Mascarella SW, Kwon YW, Triggle DJ..  (1992)  Synthesis and muscarinic receptor activity of ester derivatives of 2-substituted 2-azabicyclo[2.2.1]heptan-5-ol and -6-ol.,  35  (12): [PMID:1613746] [10.1021/jm00090a006]
24. Bräuner-Osborne H, Ebert B, Brann MR, Falch E, Krogsgaard-Larsen P..  (1995)  Annulated heterocyclic bioisosteres of norarecoline. Synthesis and molecular pharmacology at five recombinant human muscarinic acetylcholine receptors.,  38  (12): [PMID:7783150] [10.1021/jm00012a019]
25. Kim MG, Bodor ET, Wang C, Harden TK, Kohn H..  (2003)  C(8) substituted 1-azabicyclo[3.3.1]non-3-enes and C(8) substituted 1-azabicyclo[3.3.1]nonan-4-ones: novel muscarinic receptor antagonists.,  46  (11): [PMID:12747793] [10.1021/jm020572p]
26. Sauerberg P, Olesen PH, Nielsen S, Treppendahl S, Sheardown MJ, Honoré T, Mitch CH, Ward JS, Pike AJ, Bymaster FP..  (1992)  Novel functional M1 selective muscarinic agonists. Synthesis and structure-activity relationships of 3-(1,2,5-thiadiazolyl)-1,2,5,6-tetrahydro-1-methylpyridines .,  35  (12): [PMID:1613751] [10.1021/jm00090a019]
27. Daly JW, Gupta TH, Padgett WL, Pei XF..  (2000)  6beta-Acyloxy(nor)tropanes: affinities for antagonist/agonist binding sites on transfected and native muscarinic receptors.,  43  (13): [PMID:10891110] [10.1021/jm9904001]
28. Tecle H, Barrett SD, Lauffer DJ, Augelli-Szafran C, Brann MR, Callahan MJ, Caprathe BW, Davis RE, Doyle PD, Eubanks D, Lipiniski W, Mirzadegan T, Moos WH, Moreland DW, Nelson CB, Pavia MR, Raby C, Schwarz RD, Spencer CJ, Thomas AJ, Jaen JC..  (1998)  Design and synthesis of m1-selective muscarinic agonists: (R)-(-)-(Z)-1-Azabicyclo[2.2.1]heptan-3-one, O-(3-(3'-methoxyphenyl)-2-propynyl)oxime maleate (CI-1017), a functionally m1-selective muscarinic agonist.,  41  (14): [PMID:9651157] [10.1021/jm960683m]
29. Street LJ, Baker R, Book T, Kneen CO, MacLeod AM, Merchant KJ, Showell GA, Saunders J, Herbert RH, Freedman SB..  (1990)  Synthesis and biological activity of 1,2,4-oxadiazole derivatives: highly potent and efficacious agonists for cortical muscarinic receptors.,  33  (10): [PMID:2213823] [10.1021/jm00172a003]
30. Shapiro G, Floersheim P, Boelsterli J, Amstutz R, Bolliger G, Gammenthaler H, Gmelin G, Supavilai P, Walkinshaw M..  (1992)  Muscarinic activity of the thiolactone, lactam, lactol, and thiolactol analogues of pilocarpine and a hypothetical model for the binding of agonists to the m1 receptor.,  35  (1): [PMID:1732522] [10.1021/jm00079a002]
31. Bruno-Blanch L, Gálvez J, García-Domenech R..  (2003)  Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.,  13  (16): [PMID:12873507] [10.1016/s0960-894x(03)00535-3]
32. Dunbar PG, Durant GJ, Rho T, Ojo B, Huzl JJ, Smith DA, el-Assadi AA, Sbeih S, Ngur DO, Periyasamy S..  (1994)  Design, synthesis, and neurochemical evaluation of 2-amino-5-(alkoxycarbonyl)-3,4,5,6-tetrahydropyridines and 2-amino-5-(alkoxycarbonyl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists.,  37  (17): [PMID:8064804] [10.1021/jm00043a016]
33. Sauerberg P, Jeppesen L, Olesen PH, Sheardown MJ, Fink-Jensen A, Rasmussen T, Rimvall K, Shannon HE, Bymaster FP, DeLapp NW, Calligaro DO, Ward JS, Whitesitt CA, Thomsen C..  (1998)  Identification of side chains on 1,2,5-thiadiazole-azacycles optimal for muscarinic m1 receptor activation.,  (20): [PMID:9873644] [10.1016/s0960-894x(98)00509-5]
34. Yang R, Zhao R, Chen D, Shan L, Yun L, Wang H..  (2004)  Discovering selective agonists of endothelial target for acetylcholine (ETA) via diversity-guided pharmacophore simplification and simulation.,  14  (12): [PMID:15149637] [10.1016/j.bmcl.2004.04.042]
35. Street LJ, Baker R, Book T, Reeve AJ, Saunders J, Willson T, Marwood RS, Patel S, Freedman SB..  (1992)  Synthesis and muscarinic activity of quinuclidinyl- and (1-azanorbornyl)pyrazine derivatives.,  35  (2): [PMID:1732546] [10.1021/jm00080a014]
36. Valli MJ, Tang Y, Kosh JW, Chapman JM, Sowell JW..  (1992)  Synthesis and cholinergic properties of N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamino analogs of ranitidine.,  35  (17): [PMID:1507203] [10.1021/jm00095a008]
37. Triggle DJ, Kwon YW, Abraham P, Pitner JB, Mascarella SW, Carroll FI..  (1991)  Synthesis, molecular modeling studies, and muscarinic receptor activity of azaprophen analogues.,  34  (11): [PMID:1956033] [10.1021/jm00115a003]
38. Lundkvist JR, Vargas HM, Caldirola P, Ringdahl B, Hacksell U..  (1990)  Resolved pyrrolidine, piperidine, and perhydroazepine analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.,  33  (12): [PMID:2258904] [10.1021/jm00174a014]
39. Trybulski EJ, Kramss RH, Mangano RM, Rusinko A..  (1990)  Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).,  33  (12): [PMID:2258905] [10.1021/jm00174a015]
40. Nilsson BM, Vargas HM, Hacksell U..  (1992)  Urea and 2-imidazolidone derivatives of the muscarinic agents oxotremorine and N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.,  35  (17): [PMID:1507212] [10.1021/jm00095a025]
41. Trybulski EJ, Zhang J, Kramss RH, Mangano RM..  (1993)  The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives.,  36  (23): [PMID:8246221] [10.1021/jm00075a007]
42. Moltzen EK, Pedersen H, Bøgesø KP, Meier E, Frederiksen K, Sánchez C, Løve Lembøl H..  (1994)  Bioisosteres of arecoline: 1,2,3,6-tetrahydro-5-pyridyl-substituted and 3-piperidyl-substituted derivatives of tetrazoles and 1,2,3-triazoles. Synthesis and muscarinic activity.,  37  (24): [PMID:7990109] [10.1021/jm00050a006]
43. Wu ES, Kover A, Semus SF..  (1998)  Synthesis and modeling studies of a potent conformationally rigid muscarinic agonist: 1-azabicyclo[2.2.1]heptanespirofuranone.,  41  (22): [PMID:9784090] [10.1021/jm980192x]
44. Bromidge SM, Brown F, Cassidy F, Clark MS, Dabbs S, Hadley MS, Hawkins J, Loudon JM, Naylor CB, Orlek BS, Riley GJ..  (1997)  Design of [R-(Z)]-(+)-alpha-(methoxyimino)-1-azabicyclo[2.2.2]octane-3-acetonitri le (SB 202026), a functionally selective azabicyclic muscarinic M1 agonist incorporating the N-methoxy imidoyl nitrile group as a novel ester bioisostere.,  40  (26): [PMID:9435896] [10.1021/jm9702903]
45. Cao Y, Zhang M, Wu C, Lee S, Wroblewski ME, Whipple T, Nagy PI, Takács-Novák K, Balázs A, Torös S, Messer WS..  (2003)  Synthesis and biological characterization of 1-methyl-1,2,5,6-tetrahydropyridyl-1,2,5-thiadiazole derivatives as muscarinic agonists for the treatment of neurological disorders.,  46  (20): [PMID:13678406] [10.1021/jm0301235]
46. Rajeswaran WG, Cao Y, Huang XP, Wroblewski ME, Colclough T, Lee S, Liu F, Nagy PI, Ellis J, Levine BA, Nocka KH, Messer WS..  (2001)  Design, synthesis, and biological characterization of bivalent 1-methyl-1,2,5,6-tetrahydropyridyl-1,2,5-thiadiazole derivatives as selective muscarinic agonists.,  44  (26): [PMID:11741475] [10.1021/jm0102405]
47. Saunders J, Showell GA, Snow RJ, Baker R, Harley EA, Freedman SB..  (1988)  2-Methyl-1,3-dioxaazaspiro[4.5]decanes as novel muscarinic cholinergic agonists.,  31  (2): [PMID:3339620] [10.1021/jm00397a039]
48. Schickaneder H, Engler H, Szelenyi I..  (1987)  2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives: new bronchosecretolytic agents.,  30  (3): [PMID:3820227] [10.1021/jm00386a018]
49. Nilsson BM, Ringdahl B, Hacksell U..  (1988)  Derivatives of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.,  31  (3): [PMID:3346873] [10.1021/jm00398a015]
50. Tecle H, Jaen J, Augelli-Szafran C, Barrett S, Caprathe B, Lauffer D, Mirzadegan T, Moos W, Moreland D, Pavia M, Schwarz R, Thomas A, Davis R.  (1995)  Z-()-1-azabicyclo[2.2.1]heptan-3-one, O-(3-aryl-2-propynyl) oximes as potential m1-subtype selective muscarinic agonists,  (6): [10.1016/0960-894X(95)00086-9]
51. Tecle H, Lauffer D, Davis R, Mirzadegan T, Moreland D, Schwan R, Thomas A, Raby C, Eubanks D, Brann M, Jaen J.  (1995)  ()-1-Azabicyclo[2.2.1]heptan-3-one, O-(3-methyl-5-aryl-2-penten-4-ynyl) oximes: Potent muscarinic agonists,  (6): [10.1016/0960-894X(95)00087-A]
52. Ringdahl B..  (1988)  5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.,  31  (3): [PMID:3346881] [10.1021/jm00398a031]
53. Messer WS, Dunbar PG, Rho T, Periyasamy S, Ngur D, Ellerbrock BR, Bohnett M, Ryan K, Durant GJ, Hoss W.  (1992)  Synthesis, biochemical activity and behavioral effects of a series of 1,4,5,6-tetrahydropyrimidines as novel ligands for M1 receptors,  (8): [10.1016/S0960-894X(00)80531-4]
54. Tecle H, Mirzadegan T, Moos W, Moreland D, Pavia M, Schwarz R, Davis R.  (1992)  A rationale for the design and synthesis of m1 selective muscarinic agonists.,  (8): [10.1016/S0960-894X(00)80538-7]
55. Trybulski EJ, Kramss RH, Mangano RM, Brabander HJ, Francisco G.  (1992)  The synthesis and structure activity relationships of enantiomerically pure hydroxylated oxotremorine derivatives,  (8): [10.1016/S0960-894X(00)80539-9]
56. Dunbar PG, Durant GJ, Fang Z, Abuh YF, el-Assadi AA, Ngur DO, Periyasamy S, Hoss WP, Messer WS..  (1993)  Design, synthesis, and neurochemical evaluation of 5-(3-alkyl-1,2,4- oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists.,  36  (7): [PMID:8464038] [10.1021/jm00059a008]
57. Lundkvist JR, Ringdahl B, Hacksell U..  (1989)  Conformationally restricted analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.,  32  (4): [PMID:2704032] [10.1021/jm00124a022]
58. Showell GA, Baker R, Davis J, Hargreaves R, Freedman SB, Hoogsteen K, Patel S, Snow RJ..  (1992)  Synthesis and in vitro biological profile of all four isomers of the potent muscarinic agonist 3-(3-methyl-1,2,4-oxadiazol-5-yl)-1-azabicyclo[2.2.1]heptane.,  35  (5): [PMID:1548680] [10.1021/jm00083a016]
59. Saunders J, Showell GA, Baker R, Freedman SB, Hill D, McKnight A, Newberry N, Salamone JD, Hirshfield J, Springer JP..  (1987)  Synthesis and characterization of all four isomers of the muscarinic agonist 2'-methylspiro[1-azabicyclo[2.2.2]octane-3,4'-[1,3]dioxolane].,  30  (6): [PMID:3585909] [10.1021/jm00389a003]
60. Scapecchi S, Matucci R, Bellucci C, Buccioni M, Dei S, Guandalini L, Martelli C, Manetti D, Martini E, Marucci G, Nesi M, Romanelli MN, Teodori E, Gualtieri F..  (2006)  Highly chiral muscarinic ligands: the discovery of (2S,2'R,3'S,5'R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine 3-sulfoxide methyl iodide, a potent, functionally selective, M2 partial agonist.,  49  (6): [PMID:16539379] [10.1021/jm0510878]
61. Husain SS, Nirthanan S, Ruesch D, Solt K, Cheng Q, Li GD, Arevalo E, Olsen RW, Raines DE, Forman SA, Cohen JB, Miller KW..  (2006)  Synthesis of trifluoromethylaryl diazirine and benzophenone derivatives of etomidate that are potent general anesthetics and effective photolabels for probing sites on ligand-gated ion channels.,  49  (16): [PMID:16884293] [10.1021/jm051207b]
62. Tejada FR, Nagy PI, Xu M, Wu C, Katz T, Dorsey J, Rieman M, Lawlor E, Warrier M, Messer WS..  (2006)  Design and synthesis of novel derivatives of the muscarinic agonist tetra(ethylene glycol)(3-methoxy-1,2,5-thiadiazol-4-yl) [3-(1-methyl-1,2,5,6-tetrahydropyrid-3-yl)-1,2,5-thiadiazol-4-yl] ether (CDD-0304): effects of structural modifications on the binding and activity at muscarinic receptor subtypes and chimeras.,  49  (25): [PMID:17149881] [10.1021/jm0606995]
63. Piergentili A, Quaglia W, Giannella M, Del Bello F, Bruni B, Buccioni M, Carrieri A, Ciattini S..  (2007)  Dioxane and oxathiane nuclei: suitable substructures for muscarinic agonists.,  15  (2): [PMID:17084634] [10.1016/j.bmc.2006.10.040]
64. Piergentili A, Quaglia W, Giannella M, Del Bello F, Buccioni M, Nesi M, Matucci R..  (2008)  Rapid novel divergent synthesis and muscarinic agonist profile of all four optical isomers of N,N,N-trimethyl(6-methyl-1,4-dioxan-2-yl)methanaminium iodide.,  18  (2): [PMID:18077164] [10.1016/j.bmcl.2007.11.073]
65. Vistoli G, Pedretti A, Dei S, Scapecchi S, Marconi C, Romanelli MN..  (2008)  Docking analyses on human muscarinic receptors: unveiling the subtypes peculiarities in agonists binding.,  16  (6): [PMID:18182302] [10.1016/j.bmc.2007.12.036]
66. Scapecchi S, Nesi M, Matucci R, Bellucci C, Buccioni M, Dei S, Guandalini L, Manetti D, Martini E, Marucci G, Romanelli MN, Teodori E, Cirilli R..  (2008)  Synthesis and pharmacological characterization of chiral pyrrolidinylfuran derivatives: the discovery of new functionally selective muscarinic agonists.,  51  (13): [PMID:18543900] [10.1021/jm800145d]
67. Hillmann P, Ko GY, Spinrath A, Raulf A, von Kügelgen I, Wolff SC, Nicholas RA, Kostenis E, Höltje HD, Müller CE..  (2009)  Key determinants of nucleotide-activated G protein-coupled P2Y(2) receptor function revealed by chemical and pharmacological experiments, mutagenesis and homology modeling.,  52  (9): [PMID:19419204] [10.1021/jm801442p]
68. Niu YY, Zhu L, Cui YY, Liu HZ, Chen HZ, Lu Y..  (2008)  The absolute configuration plays an important role in muscarinic activity of BGT-A and its analogs.,  16  (24): [PMID:19013075] [10.1016/j.bmc.2008.10.047]
69. Li JH, Han SJ, Hamdan FF, Kim SK, Jacobson KA, Bloodworth LM, Zhang X, Wess J..  (2007)  Distinct structural changes in a G protein-coupled receptor caused by different classes of agonist ligands.,  282  (36): [PMID:17623649] [10.1074/jbc.m704875200]
70. Gilligan PJ, Clarke T, He L, Lelas S, Li YW, Heman K, Fitzgerald L, Miller K, Zhang G, Marshall A, Krause C, McElroy JF, Ward K, Zeller K, Wong H, Bai S, Saye J, Grossman S, Zaczek R, Arneric SP, Hartig P, Robertson D, Trainor G..  (2009)  Synthesis and structure-activity relationships of 8-(pyrid-3-yl)pyrazolo[1,5-a]-1,3,5-triazines: potent, orally bioavailable corticotropin releasing factor receptor-1 (CRF1) antagonists.,  52  (9): [PMID:19361209] [10.1021/jm900025h]
71. Piergentili A, Quaglia W, Del Bello F, Giannella M, Pigini M, Barocelli E, Bertoni S, Matucci R, Nesi M, Bruni B, Di Vaira M..  (2009)  Properly substituted 1,4-dioxane nucleus favours the selective M3 muscarinic receptor activation.,  17  (24): [PMID:19896386] [10.1016/j.bmc.2009.10.027]
72. Navarrete-Vázquez G, Hidalgo-Figueroa S, Torres-Piedra M, Vergara-Galicia J, Rivera-Leyva JC, Estrada-Soto S, Estrada-Soto S, León-Rivera I, Aguilar-Guardarrama B, Rios-Gómez Y, Villalobos-Molina R, Ibarra-Barajas M..  (2010)  Synthesis, vasorelaxant activity and antihypertensive effect of benzo[d]imidazole derivatives.,  18  (11): [PMID:20451399] [10.1016/j.bmc.2010.04.027]
73. Tasso B, Budriesi R, Vazzana I, Ioan P, Micucci M, Novelli F, Tonelli M, Sparatore A, Chiarini A, Sparatore F..  (2010)  Novel quinolizidinyl derivatives as antiarrhythmic agents: 2. Further investigation.,  53  (12): [PMID:20509610] [10.1021/jm100298d]
74. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  (5): [PMID:17417631] [10.1038/nchembio873]
75. PubChem BioAssay data set, 
76. PubChem BioAssay data set, 
77. PubChem BioAssay data set, 
78. Torres-Piedra M, Figueroa M, Hernández-Abreu O, Ibarra-Barajas M, Navarrete-Vázquez G, Estrada-Soto S, Estrada-Soto S..  (2011)  Vasorelaxant effect of flavonoids through calmodulin inhibition: Ex vivo, in vitro, and in silico approaches.,  19  (1): [PMID:21129983] [10.1016/j.bmc.2010.10.063]
79. Ziegler N, Bätz J, Zabel U, Lohse MJ, Hoffmann C..  (2011)  FRET-based sensors for the human M1-, M3-, and M5-acetylcholine receptors.,  19  (3): [PMID:20716489] [10.1016/j.bmc.2010.07.060]
80. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]
81. Unpublished dataset, 
82. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 
83. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]
84. Lebois EP, Digby GJ, Sheffler DJ, Melancon BJ, Tarr JC, Cho HP, Miller NR, Morrison R, Bridges TM, Xiang Z, Daniels JS, Wood MR, Conn PJ, Lindsley CW..  (2011)  Development of a highly selective, orally bioavailable and CNS penetrant M1 agonist derived from the MLPCN probe ML071.,  21  (21): [PMID:21930376] [10.1016/j.bmcl.2011.08.084]
85. Melancon BJ, Gogliotti RD, Tarr JC, Saleh SA, Chauder BA, Lebois EP, Cho HP, Utley TJ, Sheffler DJ, Bridges TM, Morrison RD, Daniels JS, Niswender CM, Conn PJ, Lindsley CW, Wood MR..  (2012)  Continued optimization of the MLPCN probe ML071 into highly potent agonists of the hM1 muscarinic acetylcholine receptor.,  22  (10): [PMID:22507963] [10.1016/j.bmcl.2012.03.088]
86. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
87. Daval SB, Valant C, Bonnet D, Kellenberger E, Hibert M, Galzi JL, Ilien B..  (2012)  Fluorescent derivatives of AC-42 to probe bitopic orthosteric/allosteric binding mechanisms on muscarinic M1 receptors.,  55  (5): [PMID:22329602] [10.1021/jm201348t]
88. Rendón-Vallejo P, Hernández-Abreu O, Vergara-Galicia J, Millán-Pacheco C, Mejía A, Ibarra-Barajas M, Estrada-Soto S, Estrada-Soto S..  (2012)  Ex vivo study of the vasorelaxant activity induced by phenanthrene derivatives isolated from Maxillaria densa.,  75  (12): [PMID:23234371] [10.1021/np300508v]
89. TOMIZAWA M, YAMAMOTO I.  (1992)  Binding of Nicotinoids and the Related Compounds to the Insect Nicotinic Acetyicholine Receptor,  17  (4): [10.1584/jpestics.17.4_231]
90. YAMAMOTO I, YABUTA G, TOMIZAWA M, SAITO T, MIYAMOTO T, KAGABU S.  (1995)  Molecular Mechanism for Selective Toxicity of Nicotinoids and Neonicotinoids,  20  (1): [10.1584/jpestics.20.33]
91. TOMIZAWA M, OTSUKA H, MIYAMOTO T, YAMAMOTO I.  (1995)  Pharmacological Effects of Imidacloprid and Its Related Compounds on the Nicotinic Acetyicholine Receptor with Its Ion Channel from the Torpedo Electric Organ,  20  (1): [10.1584/jpestics.20.49]
92. TOMIZAWA M, OTSUKA H, MIYAMOTO T, ELDEFRAWI ME, YAMAMOTO I.  (1995)  Pharmacological Characteristics of Insect Nicotinic Acetyicholine Receptor with Its Ion Channel and the Comparison of the Effect of Nicotinoids and Neonicotinoids,  20  (1): [10.1584/jpestics.20.57]
93. PubChem BioAssay data set, 
94. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]
95. Hernández F, Sánchez A, Rendón-Vallejo P, Millán-Pacheco C, Alcaraz Y, Delgado F, Vázquez MA, Estrada-Soto S, Estrada-Soto S..  (2013)  Synthesis, ex vivo and in silico studies of 3-cyano-2-pyridone derivatives with vasorelaxant activity.,  70  [PMID:24212125] [10.1016/j.ejmech.2013.10.018]
96. PubChem BioAssay data set, 
97. Rodger IW, Hersom AS, Waigh RD..  (1979)  Actions of two dopamine derivatives at adreno- and cholinoceptors.,  22  (1): [PMID:423175] [10.1021/jm00187a027]
98. Del Bello F, Bonifazi A, Quaglia W, Mazzolari A, Barocelli E, Bertoni S, Matucci R, Nesi M, Piergentili A, Vistoli G..  (2014)  Mode of interaction of 1,4-dioxane agonists at the M2 and M3 muscarinic receptor orthosteric sites.,  24  (15): [PMID:24980056] [10.1016/j.bmcl.2014.06.020]
99. WHO Anatomical Therapeutic Chemical Classification, 
100. British National Formulary (72nd edition), 
101. DrugMatrix,  [10.6019/CHEMBL3885881]
102. Qu C, Ding M, Zhu Y, Lu Y, Du J, Miller M, Tian J, Zhu J, Xu J, Wen M, Er-Bu A, Wang J, Xiao Y, Wu M, McManus OB, Li M, Wu J, Luo HR, Cao Z, Shen B, Wang H, Zhu MX, Hong X..  (2017)  Pyrazolopyrimidines as Potent Stimulators for Transient Receptor Potential Canonical 3/6/7 Channels.,  60  (11): [PMID:28395140] [10.1021/acs.jmedchem.7b00304]
103. Fish I, Stößel A, Eitel K, Valant C, Albold S, Huebner H, Möller D, Clark MJ, Sunahara RK, Christopoulos A, Shoichet BK, Gmeiner P..  (2017)  Structure-Based Design and Discovery of New M2 Receptor Agonists.,  60  (22): [PMID:29094937] [10.1021/acs.jmedchem.7b01113]
104. Del Bello F, Bonifazi A, Giorgioni G, Cifani C, Micioni Di Bonaventura MV, Petrelli R, Piergentili A, Fontana S, Mammoli V, Yano H, Matucci R, Vistoli G, Quaglia W..  (2018)  1-[3-(4-Butylpiperidin-1-yl)propyl]-1,2,3,4-tetrahydroquinolin-2-one (77-LH-28-1) as a Model for the Rational Design of a Novel Class of Brain Penetrant Ligands with High Affinity and Selectivity for Dopamine D4 Receptor.,  61  (8): [PMID:29589445] [10.1021/acs.jmedchem.8b00265]
105. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]
106. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]
107. Agnetta L, Bermudez M, Riefolo F, Matera C, Claro E, Messerer R, Littmann T, Wolber G, Holzgrabe U, Decker M..  (2019)  Fluorination of Photoswitchable Muscarinic Agonists Tunes Receptor Pharmacology and Photochromic Properties.,  62  (6): [PMID:30827105] [10.1021/acs.jmedchem.8b01822]
108. Pegoli A, Wifling D, Gruber CG, She X, Hübner H, Bernhardt G, Gmeiner P, Keller M..  (2019)  Conjugation of Short Peptides to Dibenzodiazepinone-Type Muscarinic Acetylcholine Receptor Ligands Determines M2R Selectivity.,  62  (11): [PMID:31074983] [10.1021/acs.jmedchem.8b01967]
109. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
110. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]
111. Fischer O, Hofmann J, Rampp H, Kaindl J, Pratsch G, Bartuschat A, Taudte RV, Fromm MF, Hübner H, Gmeiner P, Heinrich MR..  (2020)  Regiospecific Introduction of Halogens on the 2-Aminobiphenyl Subunit Leading to Highly Potent and Selective M3 Muscarinic Acetylcholine Receptor Antagonists and Weak Inverse Agonists.,  63  (8): [PMID:32202101] [10.1021/acs.jmedchem.0c00297]
112. Lindfors L, Sundström L, Fröderberg Roth L, Meuller J, Andersson S, Kihlberg J..  (2020)  Is GPR146 really the receptor for proinsulin C-peptide?,  30  (13): [PMID:32354568] [10.1016/j.bmcl.2020.127208]
113. Unpublished dataset, 
114. Lin SX,Curtis MA,Sperry J.  (2020)  Pyridine alkaloids with activity in the central nervous system.,  28  (24): [PMID:33120080] [10.1016/j.bmc.2020.115820]
115. Köckenberger J, Fischer O, Konopa A, Bergwinkl S, Mühlich S, Gmeiner P, Kutta RJ, Hübner H, Keller M, Heinrich MR..  (2022)  Synthesis, Characterization, and Application of Muscarinergic M3 Receptor Ligands Linked to Fluorescent Dyes.,  65  (24.0): [PMID:36484801] [10.1021/acs.jmedchem.2c01376]