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Merck
CN

O9126

Oxotremorine sesquifumarate salt

≥98% (HPLC), solid

Synonym(s):

1-(4-[1-Pyrrolidinyl]-2-butynyl)-2-pyrrolidinone, 1-(4-[1-Pyrrolidinyl]2-butynyl)-2-pyrrolidinone

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About This Item

Empirical Formula (Hill Notation):
C12H18N2O · 1.5C4H4O4 · xH2O
CAS Number:
17360-35-9
Molecular Weight:
380.39 (anhydrous basis)
NACRES:
NA.77
PubChem Substance ID:
24278614
UNSPSC Code:
12352200
EC Number:
241-388-3
MDL number:
MFCD00013163
Assay:
≥98% (HPLC)
Form:
solid

Key Documents

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Product Name

Oxotremorine sesquifumarate salt, ≥98% (HPLC), solid

InChI

1S/2C12H18N2O.3C4H4O4/c2*15-12-6-5-11-14(12)10-4-3-9-13-7-1-2-8-13;3*5-3(6)1-2-4(7)8/h2*1-2,5-11H2;3*1-2H,(H,5,6)(H,7,8)/b;;3*2-1+

InChI key

WLYYOFJEBGHKEC-VQYXCCSOSA-N

SMILES string

[H]\C(=C(\[H])C(O)=O)C(O)=O.[H]\C(=C(\[H])C(O)=O)C(O)=O.[H]\C(=C(\[H])C(O)=O)C(O)=O.O=C1CCCN1CC#CCN2CCCC2.O=C3CCCN3CC#CCN4CCCC4

assay

≥98% (HPLC)

form

solid

mp

102-105 °C (lit.)

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

Gene Information

human ... CHRM2(1129)

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Biochem/physiol Actions

Oxotremorine sesquifumarate salt is a muscarinic acetylcholine receptor agonist with preference for the M2 receptor.

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000083831
0000077578
0000077577
0000064706
0000064707

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I B Introini-Collison et al.
Behavioral and neural biology, 57(3), 248-255 (1992-05-01)
Post-training administration of the centrally acting muscarinic agonist oxotremorine (50.0 microgram/kg, ip) facilitated 48-hr retention, in mice, of a one-trial step-through inhibitory avoidance response. Oxotremorine-induced memory facilitation was not prevented by the simultaneous post-training administration of the central beta-adrenoceptor antagonist
P G Gunasekar et al.
Neuroscience research, 49(1), 13-18 (2004-04-22)
Cyanide is generated in neurons and this report examines the two different receptors which mediate cyanide formation in neuronal tissue. An opiate receptor blocked by naloxone increases cyanide production both in rat brain and in rat pheochromocytoma (PC12) cells. A
J D Brioni et al.
Behavioral and neural biology, 50(3), 251-254 (1988-11-01)
The pre-test administration of beta-endorphin (0.05 microgram/mouse), oxotremorine sesquifumarate (5.0 micrograms/mouse), or beta-endorphin plus oxotremorine enhanced retention test performance of a conditioned emotional response in mice. The effects were blocked by scopolamine. Scopolamine had no effect of its own. The
T Reinheimer et al.
American journal of respiratory and critical care medicine, 156(2 Pt 1), 389-395 (1997-08-01)
Human bronchi were incubated in organ baths to measure histamine release. The calcium ionophore A23187 (10 mumol/L; 1 min) stimulated histamine release by 148 +/- 28% (n = 11) above the prestimulation level but was ineffective in epithelium-denuded bronchi. Neither
I Izquierdo et al.
Pharmacology, biochemistry, and behavior, 33(3), 545-548 (1989-07-01)
CD-1 mice were trained in a classically conditioned emotional response paradigm and tested 24 hr later. Exposure to an open field 0 or 1, but not 3 hr after training retroactively interfered with retention of the conditioned emotional response. The
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