SM-21 maleate | CAS#155058-71-2 | Sigma(2) Antagonist

MedKoo Cat#: 532755 | Name: SM-21 maleate

Description:

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

SM-21 is a potent and selective sigma(2) antagonist. SM-21 is a tropane analogue with high affinity and selectivity for sigma(2) receptor subtype. SM 21 attenuates the convulsive and locomotor stimulatory effects of cocaine in mice. (+/-)-SM 21 may be a suitable lead compound for developing sigma2-selective ligands.

Chemical Structure

SM-21 maleate

CAS#155058-71-2 (racemic free base)

Theoretical Analysis

MedKoo Cat#: 532755

Name: SM-21 maleate

CAS#: 155058-71-2 (racemic free base)

Chemical Formula: C18H24ClNO3

Exact Mass: 337.1445

Molecular Weight: 337.84

Elemental Analysis: C, 63.99; H, 7.16; Cl, 10.49; N, 4.15; O, 14.21

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450.00	2 Weeks
25mg	USD 700.00	2 Weeks

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Related CAS #

155156-22-2 (R-isomer maleate) 155058-71-2 (racemic free base) 155156-12-0 (R-isomer) 155156-13-1 (S-isomer) 155156-23-3 (S-isomer maleate)

Synonym

SM 21; SM21; SM-21; (±)-SM21; SM-21 maleate; SM-21 racemate maleate,

IUPAC/Chemical Name

(1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(4-chlorophenoxy)butanoate

InChi Key

WTPAXDRULIZRDJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H24ClNO3/c1-3-17(22-15-8-4-12(19)5-9-15)18(21)23-16-10-13-6-7-14(11-16)20(13)2/h4-5,8-9,13-14,16-17H,3,6-7,10-11H2,1-2H3

SMILES Code

CCC(OC1=CC=C(Cl)C=C1)C(O[C@H]2C[C@H](N3C)CC[C@H]3C2)=O

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

Certificate of Analysis

View CoA: current batch, Lot#A20O11B10

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 337.84 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

This message contains search results from the National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM). Do not reply directly to this message Sent On: Mon Nov 09 09:33:44 2020 Search: SM21 20 selected items PubMed Results Items 1-20 of 20 (Display the 20 citations in PubMed) 1: Udawatte NS, Kang SW, Wang Y, Arumugam TV, Seneviratne CJ. Predictive Nephrotoxicity Profiling of a Novel Antifungal Small Molecule in Comparison to Amphotericin B and Voriconazole. Front Pharmacol. 2020 Apr 24;11:511. doi: 10.3389/fphar.2020.00511. PMID: 32390849; PMCID: PMC7193989. 2: Cantonero C, Camello PJ, Abate C, Berardi F, Salido GM, Rosado JA, Redondo PC. NO1, a New Sigma 2 Receptor/TMEM97 Fluorescent Ligand, Downregulates SOCE and Promotes Apoptosis in the Triple Negative Breast Cancer Cell Lines. Cancers (Basel). 2020 Jan 21;12(2):257. doi: 10.3390/cancers12020257. PMID: 31973006; PMCID: PMC7072710. 3: Truong T, Zeng G, Lim TK, Cao T, Pang LM, Lee YM, Lin Q, Wang Y, Seneviratne CJ. Proteomics Analysis of Candida albicans dnm1 Haploid Mutant Unraveled the Association between Mitochondrial Fission and Antifungal Susceptibility. Proteomics. 2020 Jan;20(1):e1900240. doi: 10.1002/pmic.201900240. Epub 2019 Dec 18. PMID: 31811746. 4: Rahmani A, Baee M, Rostamtabar M, Karkhah A, Alizadeh S, Tourani M, Nouri HR. Development of a conserved chimeric vaccine based on helper T-cell and CTL epitopes for induction of strong immune response against Schistosoma mansoni using immunoinformatics approaches. Int J Biol Macromol. 2019 Dec 1;141:125-136. doi: 10.1016/j.ijbiomac.2019.08.259. Epub 2019 Aug 31. PMID: 31479669. 5: Zhang LN, Wang DC, Hu Q, Dai XQ, Xie YS, Li Q, Liu HM, Guo JH. Consortium of Plant Growth-Promoting Rhizobacteria Strains Suppresses Sweet Pepper Disease by Altering the Rhizosphere Microbiota. Front Microbiol. 2019 Jul 23;10:1668. doi: 10.3389/fmicb.2019.01668. PMID: 31396185; PMCID: PMC6664061. 6: Terada K, Migita K, Matsushima Y, Sugimoto Y, Kamei C, Matsumoto T, Mori M, Matsunaga K, Takata J, Karube Y. Cholinesterase inhibitor rivastigmine enhances nerve growth factor-induced neurite outgrowth in PC12 cells via sigma-1 and sigma-2 receptors. PLoS One. 2018 Dec 17;13(12):e0209250. doi: 10.1371/journal.pone.0209250. PMID: 30557385; PMCID: PMC6296549. 7: Truong T, Suriyanarayanan T, Zeng G, Le TD, Liu L, Li J, Tong C, Wang Y, Seneviratne CJ. Use of Haploid Model of Candida albicans to Uncover Mechanism of Action of a Novel Antifungal Agent. Front Cell Infect Microbiol. 2018 Jun 8;8:164. doi: 10.3389/fcimb.2018.00164. PMID: 29938200; PMCID: PMC6002804. 8: Rezende CMF, Coitinho JB, Costa M, Silva MR, Giusta M, Oliveira-Prado R, Corrêa-Oliveira R, Nagem R, Goes AM. Biochemical analysis and identification of linear B-cell epitopes from recombinant Sm21.7 antigen from Schistosoma mansoni. Mol Immunol. 2018 Sep;101:29-37. doi: 10.1016/j.molimm.2018.05.019. Epub 2018 May 29. PMID: 29857222. 9: Mukherjee C, Hale C, Mukhopadhyay S. A Simple Multistep Protocol for Differentiating Human Induced Pluripotent Stem Cells into Functional Macrophages. Methods Mol Biol. 2018;1784:13-28. doi: 10.1007/978-1-4939-7837-3_2. PMID: 29761384. 10: Trujillo AN, Katnik C, Cuevas J, Cha BJ, Taylor-Clark TE, Breslin JW. Modulation of mesenteric collecting lymphatic contractions by σ1-receptor activation and nitric oxide production. Am J Physiol Heart Circ Physiol. 2017 Oct 1;313(4):H839-H853. doi: 10.1152/ajpheart.00702.2016. Epub 2017 Aug 4. PMID: 28778917; PMCID: PMC5668603. 11: Katnik C, Garcia A, Behensky AA, Yasny IE, Shuster AM, Seredenin SB, Petrov AV, Cuevas J. Activation of σ1 and σ2 receptors by afobazole increases glial cell survival and prevents glial cell activation and nitrosative stress after ischemic stroke. J Neurochem. 2016 Nov;139(3):497-509. doi: 10.1111/jnc.13756. Epub 2016 Sep 1. PMID: 27488244. 12: Kuehnel RU, Hartrumpf M, Erb M, Albes JM. Hemodynamic Performance of Endovascular Valves as Valve-in-Valve in Small Stented Bioprosthesis. Thorac Cardiovasc Surg. 2017 Apr;65(3):225-230. doi: 10.1055/s-0036-1586492. Epub 2016 Aug 12. PMID: 27517167. 13: Thomas CM, Fitzsimmons CM, Dunne DW, Timson DJ. Comparative biochemical analysis of three members of the Schistosoma mansoni TAL family: Differences in ion and drug binding properties. Biochimie. 2015 Jan;108:40-7. doi: 10.1016/j.biochi.2014.10.015. Epub 2014 Nov 5. PMID: 25447146; PMCID: PMC4300400. 14: Soria MC, Audisio MC. Inhibition of Bacillus cereus Strains by Antimicrobial Metabolites from Lactobacillus johnsonii CRL1647 and Enterococcus faecium SM21. Probiotics Antimicrob Proteins. 2014 Dec;6(3-4):208-16. doi: 10.1007/s12602-014-9169-z. PMID: 25305011. 15: Costa MA, Rodrigues FT, Chagas BC, Rezende CM, Goes AM, Nagem RA. Preliminary crystallographic studies of a Schistosoma mansoni antigen (Sm21.7) dynein light-chain (DLC) domain. Acta Crystallogr F Struct Biol Commun. 2014 Jun;70(Pt 6):803-7. doi: 10.1107/S2053230X14009273. Epub 2014 May 24. PMID: 24915098; PMCID: PMC4051542. 16: Wong SS, Kao RY, Yuen KY, Wang Y, Yang D, Samaranayake LP, Seneviratne CJ. In vitro and in vivo activity of a novel antifungal small molecule against Candida infections. PLoS One. 2014 Jan 22;9(1):e85836. doi: 10.1371/journal.pone.0085836. PMID: 24465737; PMCID: PMC3899067. 17: Katnik C, Garcia A, Behensky AA, Yasny IE, Shuster AM, Seredenin SB, Petrov AV, Seifu S, McAleer J, Willing A, Cuevas J. Treatment with afobazole at delayed time points following ischemic stroke improves long-term functional and histological outcomes. Neurobiol Dis. 2014 Feb;62:354-64. doi: 10.1016/j.nbd.2013.10.011. Epub 2013 Oct 16. PMID: 24141021. 18: Kotagale NR, Shirbhate SH, Shukla P, Ugale RR. Agmatine attenuates neuropathic pain in sciatic nerve ligated rats: modulation by hippocampal sigma receptors. Eur J Pharmacol. 2013 Aug 15;714(1-3):424-31. doi: 10.1016/j.ejphar.2013.07.005. Epub 2013 Jul 16. PMID: 23872381. 19: Wang X, Wang J, Jin P, Zheng Y. Investigating the efficacy of Bacillus subtilis SM21 on controlling Rhizopus rot in peach fruit. Int J Food Microbiol. 2013 Jun 17;164(2-3):141-7. doi: 10.1016/j.ijfoodmicro.2013.04.010. Epub 2013 Apr 22. PMID: 23673059. 20: Kotagale NR, Mendhi SM, Aglawe MM, Umekar MJ, Taksande BG. Evidences for the involvement of sigma receptors in antidepressant like effect of quetiapine in mice. Eur J Pharmacol. 2013 Feb 28;702(1-3):180-6. doi: 10.1016/j.ejphar.2013.01.045. Epub 2013 Feb 8. PMID: 23399765.

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