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

MedKoo CAT#: 319633

CAS#: 351994-94-0

Description: Emeramide, also known as NBMI, BDTH2 or N,N'-Bis(2-mercaptoethyl)isophthalamide, is a mercury/heavy metal chelator. Emeramide molecule consists of two thiol groups and linked via a pair of amide groups. NBMI can be used to chelate heavy metals like lead, cadmium, copper, manganese, zinc, iron, and mercury from ground water, coal tailings, gold ore, waste water of battery-recycling plants, and contaminated soil. Warning: Our product, supplied as a pure chemical solid powder, has NOT been approved by FDA, is for research use only, not for human use.


Chemical Structure

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Emeramide
CAS# 351994-94-0

Theoretical Analysis

MedKoo Cat#: 319633
Name: Emeramide
CAS#: 351994-94-0
Chemical Formula: C12H16N2O2S2
Exact Mass: 284.0653
Molecular Weight: 284.39
Elemental Analysis: C, 50.68; H, 5.67; N, 9.85; O, 11.25; S, 22.55

Price and Availability

Size Price Availability Quantity
5.0g USD 150.0 Ready to ship
10.0g USD 250.0 Ready to ship
20.0g USD 450.0 Ready to ship
30.0g USD 650.0 Ready to ship
40.0g USD 850.0 Ready to ship
50.0g USD 950.0 Ready to ship
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Synonym: BDTH2; BDET; BDETH2; NBMI; Emeramide; N,N'-Bis(2-mercaptoethyl)isophthalamide; trade names B9, MetX, OSR, OSR#1.

IUPAC/Chemical Name: N1,N3-bis(2-sulfanylethyl)benzene-1,3-dicarboxamide

InChi Key: JUTBAVRYDAKVGQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H16N2O2S2/c15-11(13-4-6-17)9-2-1-3-10(8-9)12(16)14-5-7-18/h1-3,8,17-18H,4-7H2,(H,13,15)(H,14,16)

SMILES Code: O=C(C1=CC=CC(C(NCCS)=O)=C1)NCCS

Appearance: White to off-white solid powder with density 0.64 g/mL

Purity: >99% (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, not in water

Shelf Life: 2 years after customer received if the product is 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

Biological target: Emeramide is a thiol-redox antioxidant and heavy metal chelator.
In vitro activity: Even the lowest NBMI concentration (10 µM) successfully attenuated PbAc-induced toxicity by bringing the cell viability up from 42 to 83% (p < 0.0001), while the positive control DMSA did not show any impact in cell viability at even the highest concentration (100 µM) tested (Fig. 4b). Reference: Arch Toxicol. 2021 Aug;95(8):2643-2657. https://pubmed.ncbi.nlm.nih.gov/34165617/
In vivo activity: Here this study used the nematode Caenorhabditis elegans (C. elegans) to test the efficacy of NBMI in attenuating MeHg toxicity in vivo in the whole organism. The results showed that NBMI reduced both the acute toxicity (125 μM MeHg, 1 h) and chronic (5 μM MeHg, 24 h) MeHg toxicity. Co-treatment with NBMI achieved maximal efficacy against MeHg toxicity, however delayed treatment 6 days after initiation of exposure was also effective at reducing neurotoxicity. Co-treatment of NBMI reduced the worms' death rate, structural damage in DAergic neurons, and restored antioxidant response levels. Reference: Neurotox Res. 2020 Jun; 38(1): 133–144. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7924665/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 175.81
DMF 50.0 175.81

Preparing Stock Solutions

The following data is based on the product molecular weight 284.39 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. Gadde R, Betharia S. N,N'bis-(2-mercaptoethyl) isophthalamide (NBMI) exerts neuroprotection against lead-induced toxicity in U-87 MG cells. Arch Toxicol. 2021 Aug;95(8):2643-2657. doi: 10.1007/s00204-021-03103-2. Epub 2021 Jun 24. PMID: 34165617. 2. Secor JD, Kotha SR, Gurney TO, Patel RB, Kefauver NR, Gupta N, Morris AJ, Haley BE, Parinandi NL. Novel lipid-soluble thiol-redox antioxidant and heavy metal chelator, N,N'-bis(2-mercaptoethyl)isophthalamide (NBMI) and phospholipase D-specific inhibitor, 5-fluoro-2-indolyl des-chlorohalopemide (FIPI) attenuate mercury-induced lipid signaling leading to protection against cytotoxicity in aortic endothelial cells. Int J Toxicol. 2011 Dec;30(6):619-38. doi: 10.1177/1091581811422413. Epub 2011 Oct 12. PMID: 21994240; PMCID: PMC3503146. 3. Ke T, Bornhorst J, Schwerdtle T, Santamaría A, Soare FAA, Rocha JBT, Farina M, Bowman AB, Aschner M. Therapeutic Efficacy of the N,N' Bis-(2-Mercaptoethyl) Isophthalamide Chelator for Methylmercury Intoxication in Caenorhabditis elegans. Neurotox Res. 2020 Jun;38(1):133-144. doi: 10.1007/s12640-020-00194-0. Epub 2020 Mar 31. PMID: 32236898; PMCID: PMC7924665. 4. Nilsson JLÅ, Blomgren A, Nilsson UJ, Högestätt ED, Grundemar L. N,N'-Bis(2-mercaptoethyl)isophthalamide Binds Electrophilic Paracetamol Metabolites and Prevents Paracetamol-Induced Liver Toxicity. Basic Clin Pharmacol Toxicol. 2018 Nov;123(5):589-593. doi: 10.1111/bcpt.13058. Epub 2018 Jul 9. PMID: 29908097.
In vitro protocol: 1. Gadde R, Betharia S. N,N'bis-(2-mercaptoethyl) isophthalamide (NBMI) exerts neuroprotection against lead-induced toxicity in U-87 MG cells. Arch Toxicol. 2021 Aug;95(8):2643-2657. doi: 10.1007/s00204-021-03103-2. Epub 2021 Jun 24. PMID: 34165617. 2. Secor JD, Kotha SR, Gurney TO, Patel RB, Kefauver NR, Gupta N, Morris AJ, Haley BE, Parinandi NL. Novel lipid-soluble thiol-redox antioxidant and heavy metal chelator, N,N'-bis(2-mercaptoethyl)isophthalamide (NBMI) and phospholipase D-specific inhibitor, 5-fluoro-2-indolyl des-chlorohalopemide (FIPI) attenuate mercury-induced lipid signaling leading to protection against cytotoxicity in aortic endothelial cells. Int J Toxicol. 2011 Dec;30(6):619-38. doi: 10.1177/1091581811422413. Epub 2011 Oct 12. PMID: 21994240; PMCID: PMC3503146.
In vivo protocol: 1. Ke T, Bornhorst J, Schwerdtle T, Santamaría A, Soare FAA, Rocha JBT, Farina M, Bowman AB, Aschner M. Therapeutic Efficacy of the N,N' Bis-(2-Mercaptoethyl) Isophthalamide Chelator for Methylmercury Intoxication in Caenorhabditis elegans. Neurotox Res. 2020 Jun;38(1):133-144. doi: 10.1007/s12640-020-00194-0. Epub 2020 Mar 31. PMID: 32236898; PMCID: PMC7924665. 2. Nilsson JLÅ, Blomgren A, Nilsson UJ, Högestätt ED, Grundemar L. N,N'-Bis(2-mercaptoethyl)isophthalamide Binds Electrophilic Paracetamol Metabolites and Prevents Paracetamol-Induced Liver Toxicity. Basic Clin Pharmacol Toxicol. 2018 Nov;123(5):589-593. doi: 10.1111/bcpt.13058. Epub 2018 Jul 9. PMID: 29908097.

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1: Nilsson JLÅ, Blomgren A, Nilsson UJ, Högestätt ED, Grundemar L. N,N'-Bis(2-mercaptoethyl)isophthalamide Binds Electrophilic Paracetamol Metabolites and Prevents Paracetamol-Induced Liver Toxicity. Basic Clin Pharmacol Toxicol. 2018 Jun 16. doi: 10.1111/bcpt.13058. [Epub ahead of print] PubMed PMID: 29908097.

2: Anuradha R, Munisankar S, Bhootra Y, Kumar NP, Dolla C, Babu S. Malnutrition is associated with diminished baseline and mycobacterial antigen - stimulated chemokine responses in latent tuberculosis infection. J Infect. 2018 May 17. pii: S0163-4453(18)30143-9. doi: 10.1016/j.jinf.2018.05.003. [Epub ahead of print] PubMed PMID: 29777718.

3: Schutzmeier P, Focil Baquerizo A, Castillo-Tandazo W, Focil N, Bose-O'Reilly S. Efficacy of N,N'bis-(2-mercaptoethyl) isophthalamide on mercury intoxication: a randomized controlled trial. Environ Health. 2018 Feb 14;17(1):15. doi: 10.1186/s12940-018-0358-1. PubMed PMID: 29444690; PubMed Central PMCID: PMC5813329.

4: Galatianou I, Karlis G, Apostolopoulos A, Intas G, Chalari E, Gulati A, Iacovidou N, Chalkias A, Xanthos T. Body mass index and outcome of out-of-hospital cardiac arrest patients not treated by targeted temperature management. Am J Emerg Med. 2017 Sep;35(9):1247-1251. doi: 10.1016/j.ajem.2017.03.050. Epub 2017 Mar 21. PubMed PMID: 28363619.

5: Anuradha R, Munisankar S, Bhootra Y, Dolla C, Kumaran P, Babu S. High body mass index is associated with heightened systemic and mycobacterial antigen - Specific pro-inflammatory cytokines in latent tuberculosis. Tuberculosis (Edinb). 2016 Dec;101:56-61. doi: 10.1016/j.tube.2016.08.004. Epub 2016 Aug 27. PubMed PMID: 27865399.

6: Anuradha R, Munisankar S, Bhootra Y, Kumar NP, Dolla C, Kumaran P, Babu S. Coexistent Malnutrition Is Associated with Perturbations in Systemic and Antigen-Specific Cytokine Responses in Latent Tuberculosis Infection. Clin Vaccine Immunol. 2016 Apr 4;23(4):339-45. doi: 10.1128/CVI.00009-16. Print 2016 Apr. PubMed PMID: 26865593; PubMed Central PMCID: PMC4820505.

7: Chow L, Eberly LE, Austin E, Carnethon M, Bouchard C, Sternfeld B, Zhu NA, Sidney S, Schreiner P. Fitness change effects on midlife metabolic outcomes. Med Sci Sports Exerc. 2015 May;47(5):967-73. doi: 10.1249/MSS.0000000000000481. PubMed PMID: 25160846; PubMed Central PMCID: PMC4340823.

8: Frazee EN, Nystrom EM, McMahon MM, Williamson EE, Miles JM. Relationship Between Triglyceride Tolerance, Body Mass Index, and Fat Depots in Hospitalized Patients Receiving Parenteral Nutrition. JPEN J Parenter Enteral Nutr. 2015 Nov;39(8):922-8. doi: 10.1177/0148607114538059. Epub 2014 Jun 11. PubMed PMID: 24920321.

9: Uygun M, Şenay RH, Avcıbaşı N, Akgöl S. Poly(HEMA-co-NBMI) monolithic cryogel columns for IgG adsorption. Appl Biochem Biotechnol. 2014 Feb;172(3):1574-84. doi: 10.1007/s12010-013-0624-1. Epub 2013 Nov 14. PubMed PMID: 24233543.

10: Tak V, Purhoit A, Pardasani D, Garg P, Jain R, Dubey DK. Determination of alkyl alkylphosphonic acids by liquid chromatography coupled with electrospray ionization tandem mass spectrometry using a dicationic reagent. Rapid Commun Mass Spectrom. 2012 Nov 30;26(22):2637-48. doi: 10.1002/rcm.6384. PubMed PMID: 23059880.

11: Allegra E, Puzzo L, Zuccalà V, Trapasso S, Vasquez E, Garozzo A, Caltabiano R. Nuclear BMI-1 expression in laryngeal carcinoma correlates with lymph node pathological status. World J Surg Oncol. 2012 Oct 2;10:206. doi: 10.1186/1477-7819-10-206. PubMed PMID: 23031716; PubMed Central PMCID: PMC3500717.

12: Clarke D, Buchanan R, Gupta N, Haley B. Amelioration of Acute Mercury Toxicity by a Novel, Non-Toxic Lipid Soluble Chelator N,N'bis-(2-mercaptoethyl)isophthalamide: Effect on Animal Survival, Health, Mercury Excretion and Organ Accumulation. Toxicol Environ Chem. 2012;94(3):616-640. PubMed PMID: 22573916; PubMed Central PMCID: PMC3346673.

13: Patel RB, Kotha SR, Sauers LA, Malireddy S, Gurney TO, Gupta NN, Elton TS, Magalang UJ, Marsh CB, Haley BE, Parinandi NL. Thiol-redox antioxidants protect against lung vascular endothelial cytoskeletal alterations caused by pulmonary fibrosis inducer, bleomycin: comparison between classical thiol-protectant, N-acetyl-L-cysteine, and novel thiol antioxidant, N,N'-bis-2-mercaptoethyl isophthalamide. Toxicol Mech Methods. 2012 Jun;22(5):383-96. doi: 10.3109/15376516.2012.673089. PubMed PMID: 22409285; PubMed Central PMCID: PMC3914546.

14: Secor JD, Kotha SR, Gurney TO, Patel RB, Kefauver NR, Gupta N, Morris AJ, Haley BE, Parinandi NL. Novel lipid-soluble thiol-redox antioxidant and heavy metal chelator, N,N'-bis(2-mercaptoethyl)isophthalamide (NBMI) and phospholipase D-specific inhibitor, 5-fluoro-2-indolyl des-chlorohalopemide (FIPI) attenuate mercury-induced lipid signaling leading to protection against cytotoxicity in aortic endothelial cells. Int J Toxicol. 2011 Dec;30(6):619-38. doi: 10.1177/1091581811422413. Epub 2011 Oct 12. PubMed PMID: 21994240; PubMed Central PMCID: PMC3503146.

15: Gupta R, Knobel D, Gunabushanam V, Agaba E, Ritter G, Marini C, Barrera R. The effect of low body mass index on outcome in critically ill surgical patients. Nutr Clin Pract. 2011 Oct;26(5):593-7. doi: 10.1177/0884533611419666. PubMed PMID: 21947642.

16: Bredie SJ, Fouwels AJ, Wollersheim H, Schippers GM. Effectiveness of Nurse Based Motivational Interviewing for smoking cessation in high risk cardiovascular outpatients: a randomized trial. Eur J Cardiovasc Nurs. 2011 Sep;10(3):174-9. doi: 10.1016/j.ejcnurse.2010.06.003. Epub 2010 Jul 10. PubMed PMID: 20621564.

17: Laviolette L, Sava F, O'Donnell DE, Webb KA, Hamilton AL, Kesten S, Maltais F. Effect of obesity on constant workrate exercise in hyperinflated men with COPD. BMC Pulm Med. 2010 May 30;10:33. doi: 10.1186/1471-2466-10-33. PubMed PMID: 20509967; PubMed Central PMCID: PMC2891696.

18: Campana EM, Brandão AA, Pozzan R, França Mde F, Fonseca FL, Pizzi OL, Magalhães ME, Freitas EV, Brandão AP. Blood pressure in young individuals as a cardiovascular risk marker. The Rio de Janeiro study. Arq Bras Cardiol. 2009 Dec;93(6):608-15, 657-65. English, Portuguese. PubMed PMID: 20379641.

19: Garces F, López F, Niño C, Fernandez A, Chacin L, Hurt-Camejo E, Camejo G, Apitz-Castro R. High plasma phospholipase A2 activity, inflammation markers, and LDL alterations in obesity with or without type 2 diabetes. Obesity (Silver Spring). 2010 Oct;18(10):2023-9. doi: 10.1038/oby.2010.9. Epub 2010 Feb 4. PubMed PMID: 20134414.

20: Owens LA, O'Sullivan EP, Kirwan B, Avalos G, Gaffney G, Dunne F; ATLANTIC DIP Collaborators. ATLANTIC DIP: the impact of obesity on pregnancy outcome in glucose-tolerant women. Diabetes Care. 2010 Mar;33(3):577-9. doi: 10.2337/dc09-0911. Epub 2010 Jan 12. PubMed PMID: 20067952; PubMed Central PMCID: PMC2827510.



Additional Information

Warning message from MedKoo:
1. Our product has not been approved by FDA, should not be used for human. We only sell it for research use.
2. Emeramide we are supplying is guaranteed to have excellent quality. However, it is not pharmaceutical grade ( i.e. not made under GMP guideline). Our emeramide is intended for research and development use only, is not intended for use in humans or animals. This means that our product must not – under any circumstance – be purchased for human, drug, food, cosmetic, agricultural or domestic use. It should only be used by trained scientists working under controlled conditions who are familiar with the potential hazards. Moreover, for safety and regulation compliance, we only accept order from business, and we do not ship product to residential address. CUSTOMERS MUST SIGN THE LIMITED USE AGREEMENT BEFORE ORDERING EMERAMIDE. Please email to cchen@medkoo.com to request the "limited use agreement for emeramide".
3. Customer, who does not know how to use this product, should not order it from us since we will not provide "how-to-use instruction".