Oxotremorine M | CAS# 3854-04-4 | Muscarinic acetylcholine receptor agonist

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

MedKoo CAT#: 574382

CAS#: 3854-04-4

Description: Oxotremorine M is a non-selective muscarinic (M) acetylcholine receptor agonist that induces phosphoinositide hydrolysis in the ileum and increases M4-induced inhibition of calcium currents in neuroblastoma cells.

Chemical Structure

Oxotremorine M

CAS# 3854-04-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 574382
Name: Oxotremorine M
CAS#: 3854-04-4
Chemical Formula: C11H19IN2O
Exact Mass: 322.05
Molecular Weight: 322.191
Elemental Analysis: C, 41.01; H, 5.94; I, 39.39; N, 8.69; O, 4.97

Price and Availability

Size	Price	Availability
50mg	USD 240	2 Weeks
100mg	USD 395	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Oxotremorine M

IUPAC/Chemical Name: N,N,N-trimethyl-4-(2-oxo-1-pyrrolidinyl)-2-butyn-1-aminium, monoiodide

InChi Key: VVLMSCJCXMBGDI-UHFFFAOYSA-M

InChi Code: 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

SMILES Code: O=C1CCCN1CC#CC[N+](C)(C)C.[I-]

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

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Product Data:

Product Data

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Biological target:	Oxotremorine M is a non-selective muscarinic (M) acetylcholine receptor agonist.
In vitro activity:	This study found that KCNQ2/3 currents were inhibited when Oxo-M (oxotremorine M) was applied during an ongoing KCNQ2/3 response, an effect that was not blocked by atropine, suggesting that Oxo-M inhibits KCNQ2/3 channels directly. Indeed, also in oocytes that were transfected with only KCNQ2/3 channels, but not with muscarinic M1 receptors, Oxo-M inhibited the KCNQ2/3 response. These results show that besides the usual muscarinic acetylcholine receptor-mediated inhibition, Oxo-M also inhibits KCNQ2/3 channels by a direct mechanism. Reference: Eur J Pharmacol. 2016 Nov 15;791:221-228. https://pubmed.ncbi.nlm.nih.gov/27590358/
In vivo activity:	In urinary bladder from wild-type mice, the muscarinic agonist oxotremorine-M, elicited a robust phosphoinositide response characterized by an EC50 value of 0.22 microM and a maximal response (Emax) of 32.8% conversion of [3H]inositol-labeled phosphoinositides into [3H]inositol phosphates. In ilea from wild-type and M2 knockout mice, substantial phosphoinositide responses to oxotremorine-M were measured, characterized by EC50 values of 0.37 and 0.52 microM and Emax values of 35.8 and 34.7%, respectively. Oxotremorine-M also elicited phosphoinositide hydrolysis in ilea from M3 and M2/M3 knockout mice, although these responses were less sensitive (EC50 values of 1.6 and 1.4 microM; Emax values of 31.2 and 20.8%, respectively). Reference: J Pharmacol Exp Ther. 2006 Aug;318(2):649-56. https://pubmed.ncbi.nlm.nih.gov/16675640/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	125.0	387.97
	Water	20.3	62.93

Preparing Stock Solutions

The following data is based on the product molecular weight 322.19 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.

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. Zwart R, Reed H, Clarke S, Sher E. A novel muscarinic receptor-independent mechanism of KCNQ2/3 potassium channel blockade by Oxotremorine-M. Eur J Pharmacol. 2016 Nov 15;791:221-228. doi: 10.1016/j.ejphar.2016.08.037. Epub 2016 Aug 31. PMID: 27590358. 2. Tran JA, Matsui M, Ehlert FJ. Differential coupling of muscarinic M1, M2, and M3 receptors to phosphoinositide hydrolysis in urinary bladder and longitudinal muscle of the ileum of the mouse. J Pharmacol Exp Ther. 2006 Aug;318(2):649-56. doi: 10.1124/jpet.106.103093. Epub 2006 May 4. PMID: 16675640. 3. Ichikawa J, Chung YC, Li Z, Dai J, Meltzer HY. Cholinergic modulation of basal and amphetamine-induced dopamine release in rat medial prefrontal cortex and nucleus accumbens. Brain Res. 2002 Dec 20;958(1):176-84. doi: 10.1016/s0006-8993(02)03692-2. PMID: 12468043.
In vitro protocol:	1. Zwart R, Reed H, Clarke S, Sher E. A novel muscarinic receptor-independent mechanism of KCNQ2/3 potassium channel blockade by Oxotremorine-M. Eur J Pharmacol. 2016 Nov 15;791:221-228. doi: 10.1016/j.ejphar.2016.08.037. Epub 2016 Aug 31. PMID: 27590358.
In vivo protocol:	1. Tran JA, Matsui M, Ehlert FJ. Differential coupling of muscarinic M1, M2, and M3 receptors to phosphoinositide hydrolysis in urinary bladder and longitudinal muscle of the ileum of the mouse. J Pharmacol Exp Ther. 2006 Aug;318(2):649-56. doi: 10.1124/jpet.106.103093. Epub 2006 May 4. PMID: 16675640. 2. Ichikawa J, Chung YC, Li Z, Dai J, Meltzer HY. Cholinergic modulation of basal and amphetamine-induced dopamine release in rat medial prefrontal cortex and nucleus accumbens. Brain Res. 2002 Dec 20;958(1):176-84. doi: 10.1016/s0006-8993(02)03692-2. PMID: 12468043.

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1. Tran, J.A., Matsui, M., and Ehlert, F.J. Differential coupling of muscarinic M1, M2, and M3 receptors to phosphoinositide hydrolysis in urinary bladder and longitudinal muscle of the ileum of the mouse. J. Pharmacol. Exp. Ther. 318(2), 649-656 (2006).

2. Caulfield, M.P., and Brown, D.A. Pharmacology of the putative M4 muscarinic receptor mediating Ca-current inhibition in neuroblastoma x glioma hybrid (NG 108-15) cells. Br. J. Pharmacol. 104(1), 39-44 (1991).

3. Zwart, R., Reed, H., Clarke, S., et al. A novel muscarinic receptor-independent mechanism of KCNQ2/3 potassium channel blockade by Oxotremorine-M. Eur. J. Pharmacol. 791, 221-228 (2016).

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