NBMI: Chemical Identity, Molecular Structure, and Naming Evolution

NBMI (Emeramide): Chemical Identity & Naming Evolution title graphic showing the NBMI structure

Executive Summary

This research report provides a detailed examination of the molecule NBMI (N,N’-bis(2-mercaptoethyl)isophthalamide), synthesizing insights from both pre-existing notebook literature and web sources. The document outlines its precise chemical structure, molecular properties, and the step-by-step evolution of its nomenclature across environmental chemistry, dietary supplementation, preclinical toxicology, and formal clinical drug development.

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NBMI Chemical Evolution

1. Chemical Structure & Molecular Architecture

  1. Chemical Formula: C12H16N2O2S2
  2. Molecular Weight: 284.39 g/mol
  3. IUPAC / Systematic Name: N1,N3-bis(2-sulfanylethyl)benzene-1,3-dicarboxamide (also designated 1,3-benzenediamidoethanethiol)
  4. CAS Registry Number: 351994-94-0
  5. Key Structural Features:
    1. Central Iso-phthaloyl Core: A hydrophobic 1,3-disubstituted benzene ring backbone.
    2. Dual Amide Linkages: Two carbonyl-amide chains attached at positions 1 and 3 of the benzene ring.
    3. Cysteamine Arm Extensions: Each arm terminates in a nucleophilic sulfhydryl (thiol, -SH) group.
    4. Lipid Solubility: Unlike traditional hydrophilic heavy metal chelators (such as DMSA or EDTA), the aromatic ring and amide linkages grant NBMI high lipophilicity, allowing it to readily cross cell membranes and reach the inside of cells. In rats, orally given NBMI reached the brain (Clarke et al., 2012).
    5. Chelation Mechanism: The molecule functions as a multidentate lipophilic ligand. The two sulfur atoms form exceptionally strong, covalent/coordination bonds with soft heavy metals (particularly Hg2+, Pb2+, and Cd2+), effectively locking the metal in a stable, insoluble, non-toxic complex.

2. Historical & Naming Evolution Across Fields

NBMI was invented in Dr. David Atwood’s lab at the University of Kentucky, and the patent is held by the University of Kentucky Research Foundation. Around 2006–2007, Dr. Boyd Haley’s company licensed it from the university for therapeutic use, then spent years making it a drug candidate: he refined the synthesis, worked with contract manufacturers to scale it to pharmaceutical-grade purity, and earned his own patents on its medical uses.

The designation of this molecule has evolved through distinct stages as its application shifted from environmental engineering to clinical medicine:

Phase 1: Environmental Remediation (BDET / BDETH₂ / MetX)

  1. Designations: BDET, BDETH2, MetX, B9.
  2. Context: Invented in Dr. David Atwood’s lab at the University of Kentucky as a heavy metal precipitant.
  3. Primary Application: Applied in environmental engineering to treat acid mine drainage (AMD) and industrial wastewater (Matlock et al., 2002). BDET bound toxic metals such as iron, lead, and mercury, forming highly stable precipitates that resisted leaching across extreme acid and base conditions. In one acid mine drainage sample, it lowered dissolved iron from 194 ppm to below 0.009 ppm (Matlock et al., 2002).

Phase 2: Early Commercial & Dietary Supplement Era (OSR / OSR#1)

  1. Designations: OSR, OSR#1 (Oxidative Stress Reliever).
  2. Context: Marketed briefly as a lipophilic antioxidant dietary supplement by CTI Science. About 2.5 million doses of OSR#1 were sold from 2008 to 2010 with no reported safety issues.
  3. Primary Focus: Highlighted for its ability to scavenge reactive oxygen species (ROS) and replenish intracellular glutathione pools in tissues undergoing severe oxidative distress.

Phase 3: Preclinical Toxicological Studies (NBMI)

  1. Designations: NBMI (N,N’-bis(2-mercaptoethyl)isophthalamide).
  2. Context: Adopted in formal academic preclinical literature (e.g., Secor et al., 2011; Clarke et al., 2012).
  3. Primary Discoveries: Investigated in rodent models and cell culture lines. Studies showed NBMI reversed mercury-induced phospholipase D (PLD) activation, prevented ERK1/2 phosphorylation, and restored intracellular glutathione levels. NBMI saved rats from up to 14 times a mercury dose that killed every untreated animal (Clarke et al., 2012).

Phase 4: Pharmaceutical Drug Development (Emeramide / Irminix)

  1. Designations: Emeramide, Irminix (developed by EmeraMed).
  2. Context: Formal drug development pipeline as an orphan drug candidate.
  3. Primary Target: Clinical trials for acute and chronic heavy metal poisoning (mercury, lead), iron overload, and oxidative stress-mediated disorders.
  4. Iron Overload Research: In mice, NBMI lowered liver iron by 53% (Cheng et al., 2022, Archives of Toxicology). In a 28-day Phase 2a study of 13 patients with thalassemia (EMERA007), ferritin held steady.

*Click any graphic to view a larger version.

The Constant vs. The Complexity: 3D ball-and-stick model of NBMI beside a web of its names (BDET, MetX, B9, OSR#1, NBMI, Emeramide, Irminix)
NBMI structure diagram: 1,3-disubstituted benzene core, two amide linkages at positions 1 and 3, and two cysteamine arms ending in thiol (-SH) groups
Illustration of lipophilic NBMI crossing a cell membrane and one NBMI molecule binding a mercury ion (Hg2+) through its two sulfur atoms, compared with hydrophilic DMSA
The Unified Chemical Fingerprint: NBMI melting point, density, molecular weight 284.39 g/mol, IUPAC name and SMILES string
Phase 1 Environmental Remediation (BDET, BDETH2, MetX, B9) and Phase 2 Dietary Supplement Era (OSR, OSR#1)
Phase 3 Preclinical Toxicological Studies (NBMI) and Phase 4 Pharmaceutical Drug Development (Emeramide, Irminix)
The Nomenclature Rosetta Stone: table of NBMI primary names, alternative synonyms and core use cases by era
Diagnostic Crosswalk: molecular targets of MetX/BDET, OSR#1, NBMI and Emeramide/Irminix around the formula C12H16N2O2S2

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NBMI Chemical Structure and Naming Evolution

3. Comprehensive Synonyms and Chemical Identifier Matrix

Field / EraPrimary NameAlternative SynonymsCore Use Case
EnvironmentalBDET / BDETH2MetX, B9Heavy metal precipitation in acid mine drainage & wastewater
Supplement EraOSR#1OSRLipophilic antioxidant & hydroxyl radical scavenger
Preclinical ResearchNBMIN,N’-bis(2-mercaptoethyl)isophthalamideCellular stress, mercury toxicity & PLD signaling research
PharmaceuticalEmeramideIrminixOrphan drug candidate for clinical heavy metal chelation

NBMI Today: From Lab to Water Treatment

NBMI was invented to remove metals from water, and that’s where its first research was done. In 2002 and 2003, Matlock and colleagues at the University of Kentucky reported that it bound iron, lead and mercury in acid mine drainage. In one sample it lowered dissolved iron from 194 ppm to below 0.009 ppm. Lisa Blue’s 2010 University of Kentucky dissertation took it further, using NBMI in columns that brought mercury and arsenic down to below detection limits, including in a field test on arsenic-contaminated wells in West Bengal, India.

NBMI works well in water because of how it holds metals. Its two sulfur arms lock onto a metal atom and form a stable, insoluble solid that settles out and doesn’t release the metal again. That lets the metal be filtered and removed instead of staying dissolved in the water.

Purify Water LLC builds on this research with NBMI products made for water treatment. Learn more about PurifyWater Water Filter Refill Single.

Disclaimer: Purify Water NBMI products are sold for water treatment only. They are not intended for human or animal consumption and are not a drug, dietary supplement or medical treatment. They are not intended to diagnose, treat, cure or prevent any disease. Do not ingest. The research described in this article, including studies of NBMI in people and animals, is provided for scientific and historical context and does not describe uses of Purify Water products.