ML213 | CID-3111211 | CAS#489402-47-3 | KCNQ4 Channel Activator| MedKoo

MedKoo Cat#: 532191 | Name: ML213

Description:

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

ML213, also known as CID-3111211, is a selective KV7.2 (KCNQ2) and KV7.4 (KCNQ4) channel opener (EC50 values are 230 and 510 nM for KV7.2 and KV7.4 respectively). ML213 displays > 80-fold selectivity against KV7.1, KV7.3 and KV7.5 in a thallium-based fluorescence assay.

Chemical Structure

ML213

CAS#489402-47-3

Theoretical Analysis

MedKoo Cat#: 532191

Name: ML213

CAS#: 489402-47-3

Chemical Formula: C17H23NO

Exact Mass: 257.1780

Molecular Weight: 257.38

Elemental Analysis: C, 79.33; H, 9.01; N, 5.44; O, 6.22

Price and Availability

Size	Price	Availability
100mg	USD 550.00	2 Weeks
200mg	USD 950.00	2 Weeks
500mg	USD 1,850.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,250.00	2 Weeks

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Related CAS #

No Data

Synonym

ML213; ML 213; ML-213; CID-3111211; CID 3111211; CID3111211.

IUPAC/Chemical Name

N-(2,4,6-trimethylphenyl)bicyclo[2.2.1]heptane-6-carboxamide

InChi Key

SIQGKPGBLYKQBB-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H23NO/c1-10-6-11(2)16(12(3)7-10)18-17(19)15-9-13-4-5-14(15)8-13/h6-7,13-15H,4-5,8-9H2,1-3H3,(H,18,19)

SMILES Code

O=C(C1CC2CCC1C2)NC3=C(C)C=C(C)C=C3C

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

>2 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

Product Data

Instruction

View handling instruction

Biological target:

ML213 is a selective activator of Kv7.2 and Kv7.4 channels, enhances Kv7.2 and Kv7.4 channels with EC50s of 230 and 510 nM.

In vitro activity:

Despite its previous description as a selective activator of Kv7.2 and Kv7.4, ML213 significantly increased the maximum conductance of homomeric Kv7.4 and Kv7.5, as well as heteromeric Kv7.4/7.5 channels, and induced a negative shift of their activation curves. Current deactivation rates decreased in the presence of the ML213 (10 μM) for all three channel combinations. Reference: Mol Pharmacol. 2014 Sep;86(3):330-41. https://pubmed.ncbi.nlm.nih.gov/24944189/

In vivo activity:

Following contraction with the α1-adrenoceptor agonist methoxamine, application of increasing concentrations of ML213 and NS15370 to segments of rat thoracic aorta, renal artery and mesenteric artery resulted in concentration-dependent relaxations, which were considerably different from the minimal loss of tone seen when vehicle alone was applied (Figure 2A). When comparing the three arteries, ML213 and NS15370 were more potent at relaxing precontracted segments of mesenteric artery than the thoracic aorta and renal artery (n = 7–10; Table 2). Reference: Br J Pharmacol. 2014 Oct;171(19):4413-24. https://pubmed.ncbi.nlm.nih.gov/24909207/

	Solvent	mg/mL	mM
Solubility
	DMSO	19.9	77.26
	Ethanol	13.6	52.93

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 257.38 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. Brueggemann LI, Haick JM, Cribbs LL, Byron KL. Differential activation of vascular smooth muscle Kv7.4, Kv7.5, and Kv7.4/7.5 channels by ML213 and ICA-069673. Mol Pharmacol. 2014 Sep;86(3):330-41. doi: 10.1124/mol.114.093799. Epub 2014 Jun 18. PMID: 24944189; PMCID: PMC4152906. 2. Yu H, Wu M, Townsend SD, Zou B, Long S, Daniels JS, McManus OB, Li M, Lindsley CW, Hopkins CR. Discovery, Synthesis, and Structure Activity Relationship of a Series of N-Aryl- bicyclo[2.2.1]heptane-2-carboxamides: Characterization of ML213 as a Novel KCNQ2 and KCNQ4 Potassium Channel Opener. ACS Chem Neurosci. 2011 Oct 19;2(10):572-577. doi: 10.1021/cn200065b. PMID: 22125664; PMCID: PMC3223964. 3. Baldwin SN, Forrester EA, Homer NZM, Andrew R, Barrese V, Stott JB, Isakson BE, Albert AP, Greenwood IA. Marked oestrous cycle-dependent regulation of rat arterial KV 7.4 channels driven by GPER1. Br J Pharmacol. 2023 Jan;180(2):174-193. doi: 10.1111/bph.15947. Epub 2022 Oct 11. PMID: 36085551. 4. Jepps TA, Bentzen BH, Stott JB, Povstyan OV, Sivaloganathan K, Dalby-Brown W, Greenwood IA. Vasorelaxant effects of novel Kv 7.4 channel enhancers ML213 and NS15370. Br J Pharmacol. 2014 Oct;171(19):4413-24. doi: 10.1111/bph.12805. Epub 2014 Aug 14. PMID: 24909207; PMCID: PMC4209148.

In vitro protocol:

In vivo protocol:

1. Baldwin SN, Forrester EA, Homer NZM, Andrew R, Barrese V, Stott JB, Isakson BE, Albert AP, Greenwood IA. Marked oestrous cycle-dependent regulation of rat arterial KV 7.4 channels driven by GPER1. Br J Pharmacol. 2023 Jan;180(2):174-193. doi: 10.1111/bph.15947. Epub 2022 Oct 11. PMID: 36085551. 2. Jepps TA, Bentzen BH, Stott JB, Povstyan OV, Sivaloganathan K, Dalby-Brown W, Greenwood IA. Vasorelaxant effects of novel Kv 7.4 channel enhancers ML213 and NS15370. Br J Pharmacol. 2014 Oct;171(19):4413-24. doi: 10.1111/bph.12805. Epub 2014 Aug 14. PMID: 24909207; PMCID: PMC4209148.

1: Rivera-Arconada I, Vicente-Baz J, Lopez-Garcia JA. Targeting Kv7 channels in pain pathways. Oncotarget. 2017 Feb 10. doi: 10.18632/oncotarget.15261. [Epub ahead of print] PubMed PMID: 28199957. 2: Abbott GW, Jepps TA. Kcne4 Deletion Sex-Dependently Alters Vascular Reactivity. J Vasc Res. 2016;53(3-4):138-148. PubMed PMID: 27710966; PubMed Central PMCID: PMC5166573. 3: Vicente-Baz J, Lopez-Garcia JA, Rivera-Arconada I. Effects of novel subtype selective M-current activators on spinal reflexes in vitro: Comparison with retigabine. Neuropharmacology. 2016 Oct;109:131-8. doi: 10.1016/j.neuropharm.2016.05.025. PubMed PMID: 27263036. 4: Chen X, Li W, Hiett SC, Obukhov AG. Novel Roles for Kv7 Channels in Shaping Histamine-Induced Contractions and Bradykinin-Dependent Relaxations in Pig Coronary Arteries. PLoS One. 2016 Feb 4;11(2):e0148569. doi: 10.1371/journal.pone.0148569. PubMed PMID: 26844882; PubMed Central PMCID: PMC4742238. 5: Jepps TA, Olesen SP, Greenwood IA, Dalsgaard T. Molecular and functional characterization of Kv 7 channels in penile arteries and corpus cavernosum of healthy and metabolic syndrome rats. Br J Pharmacol. 2016 May;173(9):1478-90. doi: 10.1111/bph.13444. PubMed PMID: 26802314; PubMed Central PMCID: PMC4831315. 6: Svalø J, Sheykhzade M, Nordling J, Matras C, Bouchelouche P. Functional and molecular evidence for Kv7 channel subtypes in human detrusor from patients with and without bladder outflow obstruction. PLoS One. 2015 Feb 18;10(2):e0117350. doi: 10.1371/journal.pone.0117350. PubMed PMID: 25692982; PubMed Central PMCID: PMC4333569. 7: Brueggemann LI, Haick JM, Cribbs LL, Byron KL. Differential activation of vascular smooth muscle Kv7.4, Kv7.5, and Kv7.4/7.5 channels by ML213 and ICA-069673. Mol Pharmacol. 2014 Sep;86(3):330-41. doi: 10.1124/mol.114.093799. PubMed PMID: 24944189; PubMed Central PMCID: PMC4152906. 8: Jepps TA, Bentzen BH, Stott JB, Povstyan OV, Sivaloganathan K, Dalby-Brown W, Greenwood IA. Vasorelaxant effects of novel Kv 7.4 channel enhancers ML213 and NS15370. Br J Pharmacol. 2014 Oct;171(19):4413-24. doi: 10.1111/bph.12805. PubMed PMID: 24909207; PubMed Central PMCID: PMC4209148. 9: Svalø J, Bille M, Parameswaran Theepakaran N, Sheykhzade M, Nordling J, Bouchelouche P. Bladder contractility is modulated by Kv7 channels in pig detrusor. Eur J Pharmacol. 2013 Sep 5;715(1-3):312-20. doi: 10.1016/j.ejphar.2013.05.005. PubMed PMID: 23707187. 10: Yu H, Wu M, Hopkins C, Engers J, Townsend S, Lindsley C, McManus OB, Li M. A small molecule activator of KCNQ2 and KCNQ4 channels. 2011 Mar 29 [updated 2013 Feb 28]. Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010-. Available from http://www.ncbi.nlm.nih.gov/books/NBK133435/ PubMed PMID: 23658954. 11: Yu H, Wu M, Townsend SD, Zou B, Long S, Daniels JS, McManus OB, Li M, Lindsley CW, Hopkins CR. Discovery, Synthesis, and Structure Activity Relationship of a Series of N-Aryl- bicyclo[2.2.1]heptane-2-carboxamides: Characterization of ML213 as a Novel KCNQ2 and KCNQ4 Potassium Channel Opener. ACS Chem Neurosci. 2011 Oct 19;2(10):572-577. PubMed PMID: 22125664; PubMed Central PMCID: PMC3223964.