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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
  • to treat hippocampal neurons for studying fibroblast growth factor receptor 1 (FGFR1) phosphorylation
  • to induce bladder overactivity in rats

Biochem/physiol Actions

Oxotremorine M is a nonselective muscarinic acetylcholine receptor agonist.

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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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David R Thomas et al.
Neuropharmacology, 58(8), 1206-1214 (2010-03-09)
N-desmethylclozapine (NDMC) has been reported to display partial agonism at the human recombinant and rat native M(1) mAChR, a property suggested to contribute to the clinical efficacy of clozapine. However, the profile of action of NDMC at the human native
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
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
Paola Correa et al.
PLoS genetics, 8(11), e1003015-e1003015 (2012-11-21)
Caenorhabditis elegans male copulation requires coordinated temporal-spatial execution of different motor outputs. During mating, a cloacal circuit consisting of cholinergic sensory-motor neurons and sex muscles maintains the male's position and executes copulatory spicule thrusts at his mate's vulva. However, distinct
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.
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