Oxotremorine M | CAS# 3854-04-4 | Non-selective mAChR agonist

MedKoo Cat#: 574382 | Name: Oxotremorine M

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Description:

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

Oxotremorine M is a non-selective muscarinic (M) acetylcholine receptor (mAChR) 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

Theoretical Analysis

MedKoo Cat#: 574382

Name: Oxotremorine M

CAS#: 3854-04-4

Chemical Formula: C11H19IN2O

Exact Mass: 322.0542

Molecular Weight: 322.19

Elemental Analysis: C, 41.01; H, 5.94; I, 39.39; N, 8.69; O, 4.97

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 450.00	2 Weeks
100mg	USD 650.00	2 Weeks

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Synonym

Oxotremorine M; Oxo-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

Instruction

View handling instruction

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/

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

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:

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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