Oxotremorine sesquifumarate
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 574381

CAS#: 17360-35-9

Description: Oxotremorine sesquifumarate is a muscarinic agonist.


Chemical Structure

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Oxotremorine sesquifumarate
CAS# 17360-35-9

Theoretical Analysis

MedKoo Cat#: 574381
Name: Oxotremorine sesquifumarate
CAS#: 17360-35-9
Chemical Formula: C36H48N4O14
Exact Mass: 760.32
Molecular Weight: 760.794
Elemental Analysis: C, 56.83; H, 6.36; N, 7.36; O, 29.44

Price and Availability

Size Price Availability Quantity
250mg USD 285 2 Weeks
500mg USD 485 2 Weeks
1g USD 755 2 Weeks
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Synonym: Oxotremorine sesquifumarate

IUPAC/Chemical Name: 1-(4-(pyrrolidin-1-yl)but-2-yn-1-yl)pyrrolidin-2-one sesquifumarate

InChi Key: WLYYOFJEBGHKEC-VQYXCCSOSA-N

InChi Code: 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+

SMILES Code: OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.O=C1CCCN1CC#CCN1CCCC1.O=C1CCCN1CC#CCN1CCCC1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Oxotremorine sesquifumarate is a mAChR agonist that mainly activates M2 receptors.
In vitro activity: Oxotremorine (10.5 micron) produced a paralytic effect on twitch responses of rat diaphragm in vitro to direct and indirect stimulation. The paralytic effect of oxotremorine was absent when the diaphragm was stimulated directly in the presence of hemicholinium-3 (0.42 mM), at a time when twitch responses to indirect stimulation ceased completely. Oxotremorine, at two different pharmacologically active doses, strikingly increased the resting as well as electrically evoked release of acetylcholine into the bathing fluid from the phrenic nerve-diaphragm preparation. Reference: Br J Pharmacol. 1978 Feb;62(2):195-8. https://pubmed.ncbi.nlm.nih.gov/203356/
In vivo activity: The present study was performed to examine whether cold hypersensitivity and heat hyperalgesia in rats with partial sciatic nerve injuries can be attenuated by SCS in the same way as tactile hypersensitivity and to explore a possibly synergistic effect of SCS and a muscarinic receptor agonist, oxotremorine. Oxotremorine was administered intrathecally. Tactile, cold and heat sensitivities were assessed by using von Frey filaments, cold spray and focused radiant heat, respectively. Oxotremorine i.t. dose-dependently suppressed the tactile hypersensitivity. Reference: Neurosci Lett. 2008 May 2;436(1):7-12. https://pubmed.ncbi.nlm.nih.gov/18343581/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 16.0 21.03
DMSO 59.0 77.57
Ethanol 10.0 26.29
PBS (pH 7.2) 3.0 3.94
Water 54.8 71.97

Preparing Stock Solutions

The following data is based on the product molecular weight 760.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Kim EC, Toyono T, Berlinicke CA, Zack DJ, Jurkunas U, Usui T, Jun AS. Screening and Characterization of Drugs That Protect Corneal Endothelial Cells Against Unfolded Protein Response and Oxidative Stress. Invest Ophthalmol Vis Sci. 2017 Feb 1;58(2):892-900. doi: 10.1167/iovs.16-20147. PMID: 28159976; PMCID: PMC5295784. 2. Das M, Ganguly DK, Vedasiromoni JR. Enhancement by oxotremorine of acetylcholine release from the rat phrenic nerve. Br J Pharmacol. 1978 Feb;62(2):195-8. doi: 10.1111/j.1476-5381.1978.tb08445.x. PMID: 203356; PMCID: PMC1667799. 3. Frinchi M, Nuzzo D, Scaduto P, Di Carlo M, Massenti MF, Belluardo N, Mudò G. Anti-inflammatory and antioxidant effects of muscarinic acetylcholine receptor (mAChR) activation in the rat hippocampus. Sci Rep. 2019 Oct 2;9(1):14233. doi: 10.1038/s41598-019-50708-w. PMID: 31578381; PMCID: PMC6775129. 4. Song Z, Meyerson BA, Linderoth B. Muscarinic receptor activation potentiates the effect of spinal cord stimulation on pain-related behavior in rats with mononeuropathy. Neurosci Lett. 2008 May 2;436(1):7-12. doi: 10.1016/j.neulet.2008.02.044. Epub 2008 Feb 26. PMID: 18343581.
In vitro protocol: 1. Kim EC, Toyono T, Berlinicke CA, Zack DJ, Jurkunas U, Usui T, Jun AS. Screening and Characterization of Drugs That Protect Corneal Endothelial Cells Against Unfolded Protein Response and Oxidative Stress. Invest Ophthalmol Vis Sci. 2017 Feb 1;58(2):892-900. doi: 10.1167/iovs.16-20147. PMID: 28159976; PMCID: PMC5295784. 2. Das M, Ganguly DK, Vedasiromoni JR. Enhancement by oxotremorine of acetylcholine release from the rat phrenic nerve. Br J Pharmacol. 1978 Feb;62(2):195-8. doi: 10.1111/j.1476-5381.1978.tb08445.x. PMID: 203356; PMCID: PMC1667799.
In vivo protocol: 1. Frinchi M, Nuzzo D, Scaduto P, Di Carlo M, Massenti MF, Belluardo N, Mudò G. Anti-inflammatory and antioxidant effects of muscarinic acetylcholine receptor (mAChR) activation in the rat hippocampus. Sci Rep. 2019 Oct 2;9(1):14233. doi: 10.1038/s41598-019-50708-w. PMID: 31578381; PMCID: PMC6775129. 2. Song Z, Meyerson BA, Linderoth B. Muscarinic receptor activation potentiates the effect of spinal cord stimulation on pain-related behavior in rats with mononeuropathy. Neurosci Lett. 2008 May 2;436(1):7-12. doi: 10.1016/j.neulet.2008.02.044. Epub 2008 Feb 26. PMID: 18343581.

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1. Fisher et al (1984) Differential stimulation in inositol phospholipid turnover in brain by analogs of oxotremorine. J.Neurochem. 43 1171 PMID: 6088696

2. Moroi-Fetters et al (1988) Muscarinic receptor-mediated phosphoinositide hydrolysis in the rat retina. J.Pharmacol.Exp.Ther. 246 553 PMID: 2841451