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O100

Oxotremorine M

muscarinic acetylcholine receptor agonist, 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
UNSPSC Code:
12352200
PubChem Substance ID:
24277861
NACRES:
NA.77
MDL number:
MFCD00055133
Form:
solid
Quality level:
200
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Product Name

Oxotremorine M, solid

form

solid

Quality Level

200

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
  • to induce bladder overactivity in rats[2]

Biochem/physiol Actions

Oxotremorine M is a nonselective muscarinic acetylcholine receptor agonist.[3]

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.

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This Item
T9778SML0790G0544
Oxotremorine M solid

Sigma-Aldrich

O100

Oxotremorine M

Tropicamide solid

Sigma-Aldrich

T9778

Tropicamide

Iperoxo ≥98% (HPLC)

Sigma-Aldrich

SML0790

Iperoxo

GR 103691 ≥98% (HPLC), solid

Sigma-Aldrich

G0544

GR 103691

form

solid

form

solid

form

powder

form

solid

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

H2O: 24 mg/mL, ethanol: 4.6 mg/mL

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 4.3 mg/mL, ethanol: 5.6 mg/mL, H2O: insoluble

solubility

H2O: 5 mg/mL, clear (warmed)

solubility

DMSO: soluble >5 mg/mL at 60 °C

color

white

color

white

color

white to beige

color

white

Gene Information

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

Gene Information

human ... CHRM3(1131), CHRM4(1132)

Gene Information

-

Gene Information

rat ... Htr1a(24473)

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

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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Detection of Fibroblast Growth Factor Receptor 1 (FGFR1) Transactivation by Muscarinic Acetylcholine Receptors (mAChRs) in Primary Neuronal Hippocampal Cultures Through Use of Biochemical and Morphological Approaches
"Reference Module in Food Science, 57-70 (2018)
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
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.
View All Related Papers

Global Trade Item Number

SKUGTIN
O100-500MG04061838065063
O100-100MG04061834212690

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