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O100

Sigma-Aldrich

Oxotremorine M

solid

Synonym(s):

N,N,N,-Trimethyl-4-(2-oxo-1-pyrrolidinyl)-2-butyn-1-ammonium iodide, Oxotremorine methiodide

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About This Item

Empirical Formula (Hill Notation):
C11H19IN2O
CAS Number:
63939-65-1
Molecular Weight:
322.19
MDL number:
MFCD00055133
UNSPSC Code:
12352200
PubChem Substance ID:
24277861
NACRES:
NA.77

form

solid

color

white

solubility

H2O: 24 mg/mL
ethanol: 4.6 mg/mL

storage temp.

2-8°C

SMILES string

[I-].C[N+](C)(C)CC#CCN1CCCC1=O

InChI

1S/C11H19N2O.HI/c1-13(2,3)10-5-4-8-12-9-6-7-11(12)14;/h6-10H2,1-3H3;1H/q+1;/p-1

InChI key

VVLMSCJCXMBGDI-UHFFFAOYSA-M

Gene Information

human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)

Application

Oxotremorine M has been used as a muscarinic acetylcholine receptor (mAchR) agonist:
  • to study its acute effects on the movement of Caenorhabditis elegans[1]
  • to treat hippocampal neurons for studying fibroblast growth factor receptor 1 (FGFR1) phosphorylation[2]
  • to induce bladder overactivity in rats[3]

Biochem/physiol Actions

Oxotremorine M is a nonselective muscarinic acetylcholine receptor agonist.[4]

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Acetylcholine Receptors (Muscarinic) and Acetylcholine Receptors (Nicotinic) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000366288
0000366288
0000217518
0000217518
0000184217

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M Gillard et al.
Molecular pharmacology, 32(1), 100-108 (1987-07-01)
We compared the binding characteristics of muscarinic receptors labeled by [3H]oxotremorine-M ([3H]oxo-M) in homogenates of brain cortex and heart from rat. In both tissues [3H]oxo-M bound, with the same KD (6.5 nM), to a fraction of the receptors labeled by
Simona Dedoni et al.
Journal of neurochemistry, 122(1), 58-71 (2012-04-27)
Type I interferons (IFNs) have been shown to act on neurons and to cause neuronal damage through mechanisms not completely defined. Here, we investigated the effects of type I IFNs on brain-derived neurotrophic factor (BDNF)-induced TrkB receptor signaling and neurotrophic
Yoshihiro Matsumoto et al.
Urology, 75(4), 862-867 (2010-02-17)
To investigate the effects of various muscarinic acetylcholine receptor (mAChR) antagonists, including selective M2 and M3 mAChR antagonists, on bladder overactivity. It has been proposed that the urothelium modulates the activity of bladder afferent pathways. However, the differential roles of
Li Hu et al.
Scientific reports, 10(1), 17581-17581 (2020-10-18)
SPARC-deficient mice have been shown to exhibit impaired glucose tolerance and insulin secretion, but the underlying mechanism remains unknown. Here, we showed that SPARC enhanced the promoting effect of Muscarinic receptor agonist oxotremorine-M on insulin secretion in cultured mouse islets.
Pawan Bista et al.
Pflugers Archiv : European journal of physiology, 463(1), 89-102 (2011-11-16)
Modulation of the standing outward current (I (SO)) by muscarinic acetylcholine (ACh) receptor (MAChR) stimulation is fundamental for the state-dependent change in activity mode of thalamocortical relay (TC) neurons. Here, we probe the contribution of MAChR subtypes, G proteins, phospholipase
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