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Bromocyclohexane-d11 is a stable isotope-labeled internal standard. Its unlabeled parent, bromocyclohexane, is not a pharmaceutical drug; it is an organobromine compound widely used as a synthetic intermediate in the preparation of organometallic reagents (e.g., cyclohexylmagnesium bromide, the Grignard reagent) and in nucleophilic substitution (SN1/SN2) and elimination reactions. There are no known pharmacological targets; instead, its chemical reactivity with nucleophiles is its primary characteristic. In biological systems, bromocyclohexane can undergo phase I metabolism via oxidation, primarily by cytochrome P450 enzymes, and phase II conjugation. The deuterated version is used as a tracer to study these metabolic pathways and to correct for matrix effects in analytical method development. The labeled compound is also used to investigate kinetic isotope effects (KIEs) in chemical and enzymatic reactions, where the substitution of hydrogen with deuterium alters reaction rates due to the difference in bond dissociation energies (C-D bond is stronger than C-H bond).
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
The in vitro biological activity of Bromocyclohexane-d11 has not been independently characterized, as it is used as an analytical internal standard. Its unlabeled parent, bromocyclohexane, is not a bioactive molecule with a therapeutic mechanism; however, its potential to form covalent adducts with nucleophilic groups in proteins has been studied. In rat liver microsomes, bromocyclohexane (50-500 uM) undergoes CYP450-mediated oxidation, primarily to cyclohexanol (via an epoxide intermediate), with a Vmax of ~1 nmol/min/mg protein and Km of ~200 uM. The reaction also produces cyclohexene, an elimination product. The conversion is dependent on NADPH and oxygen. In the presence of glutathione (GSH, 1-5 mM), bromocyclohexane can form GSH conjugates, indicating its potential for electrophilic reactivity. The deuterated Bromocyclohexane-d11 can be used as a substrate in these studies to measure deuterium kinetic isotope effects (KIEs) on the rate of oxidative metabolism and conjugation. The presence of eleven deuterium atoms significantly slows the rate of C-H bond cleavage in rate-limiting steps, making it a valuable probe for studying CYP450 reaction mechanisms. |
| ln Vivo |
The in vivo activity of Bromocyclohexane-d11 is not evaluated; it is used primarily as an analytical standard or chemical tracer. Its unlabeled parent, bromocyclohexane, has limited pharmacological interest but is used as a tool compound in metabolism studies. In rats, following intraperitoneal administration (50-100 mg/kg), bromocyclohexane is rapidly metabolized to cyclohexanol, which is further oxidized to cyclohexanone, and finally to dicarboxylic acids (adipic acid) which are excreted in urine. The primary route of excretion for the parent compound is via the bile (after conjugation with glutathione) and into the feces; only a small percentage (approximately 10%) is excreted unchanged in the urine. The toxicity of bromocyclohexane is low (oral LD₅0 in rats: approximately 1,600 mg/kg). Because the compound is a potential alkylating agent, chronic or high-level exposure may cause irritation and damage to the liver and kidneys. Bromocyclohexane-d11 is used as an internal standard to accurately quantify the parent compound in these toxicokinetic studies.
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| Enzyme Assay |
A generic non-cell-based assay for Bromocyclohexane-d11 involves its use as an internal standard in a GC-MS method for quantifying bromocyclohexane in organic reaction mixtures or environmental samples. Prepare a standard stock solution of unlabeled bromocyclohexane in hexane (1 mg/mL). Prepare a separate stock solution of Bromocyclohexane-d11 at the same concentration. Prepare calibration standards by spiking the unlabeled analyte into a blank matrix (e.g., hexane or a sample matrix) to achieve concentrations ranging from 1 to 500 ug/mL. Add a fixed concentration of the internal standard (e.g., 50 ug/mL) to each calibration standard. For sample preparation, simple dilution in hexane is usually sufficient unless matrix cleanup is required. Analyze by GC-MS in electron ionization (EI) mode. Monitor the characteristic mass fragments: For bromocyclohexane, the molecular ion (M+) at m/z 162 (⁷⁹Br) and 164 (⁸¹Br) is typically weak due to fragmentation; common fragment ions include m/z 83 (C₆H11+, loss of Br) and m/z 55. For Bromocyclohexane-d11, the molecular ion is at m/z 174 (C₆D11⁷⁹Br) and the major fragment due to loss of DBr is at m/z 94 (C₆D11+). Alternatively, monitor m/z 83 (for unlabeled) and m/z 94 (for labeled) as the quantitative transitions. Construct the calibration curve by plotting the peak area ratio (analyte/IS) vs. the nominal concentration. This method is used to determine reaction yields in synthetic chemistry.
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| Cell Assay |
A standard in vitro cell-based protocol for the unlabeled bromocyclohexane is not common, as it is not a drug. However, to study its metabolism, primary rat hepatocytes can be used. Isolate primary rat hepatocytes from male Sprague-Dawley rats (200-250 g) by two-step collagenase perfusion. Culture the hepatocytes in Williams‘ Medium E supplemented with 10% FBS and 1% penicillin/streptomycin, in collagen-coated 6-well plates at 5×10⁵ cells/well. After 4-6 hours of attachment, replace the medium with fresh serum-free Williams‘ Medium E. Treat the cells with increasing concentrations of unlabeled bromocyclohexane (10, 50, 100, 500 uM) or vehicle (DMSO, final concentration <0.1%) for 2, 6, 12, and 24 hours. At each time point, harvest the culture medium and cells separately. For metabolite analysis, extract 200 uL of medium with 400 uL of ethyl acetate, vortex, centrifuge, and evaporate the organic layer under nitrogen. Reconstitute in 100 uL of methanol and analyze by GC-MS for the presence of cyclohexanol and cyclohexanone. Use Bromocyclohexane-d11 as an internal standard to accurately quantify the rate of disappearance of the parent compound from the medium and the rate of appearance of metabolites. Also, measure cell viability using the LDH release assay to assess cytotoxicity (EC₅0).
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| Animal Protocol |
A typical in vivo protocol for Bromocyclohexane-d11 involves a metabolic clearance study in rats. Use male Sprague-Dawley rats (250-300 g, n = 5 per time point). Administer a single intraperitoneal (i.p.) dose of unlabeled bromocyclohexane (100 mg/kg) suspended in corn oil. For a subset of animals, co-administer Bromocyclohexane-d11 (10 mg/kg) as a tracer to follow metabolic fate. Collect blood samples via tail vein at 0, 0.5, 1, 2, 4, 6, 8, 12, 24, and 48 hours post-dose into heparinized tubes. Also collect 24-hour urine samples using metabolic cages. At the terminal time point (48 h), euthanize the rats and collect liver, kidney, and adipose tissue. For bioanalysis, process plasma, urine, and tissue homogenates: extract with ethyl acetate (1:3 v/v), centrifuge, evaporate the organic layer, and reconstitute in hexane. Analyze by GC-MS with selected ion monitoring (SIM) for m/z 83 (unlabeled) and m/z 94 (labeled). Quantify using a calibration curve prepared with the internal standard. Calculate the metabolic clearance (CL), elimination half-life (t½), and volume of distribution (Vd). Determine the fraction of the dose excreted in urine as parent compound versus oxidized metabolites (cyclohexanol, cyclohexanone, adipic acid) after derivatization (e.g., with BSTFA for GC-MS). This study is typically conducted for toxicokinetic assessment.
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| ADME/Pharmacokinetics |
Bromocyclohexane-d11 is an analytical internal standard, not a drug. The pharmacokinetics of its unlabeled parent, bromocyclohexane, are relevant primarily for toxicokinetic risk assessment. Following intraperitoneal administration in rats, bromocyclohexane is rapidly absorbed (Tmax ~ 0.5-1 hour) and distributed widely due to its moderate lipophilicity (log P ~ 3.0). The volume of distribution is approximately 1-2 L/kg. Bromocyclohexane is extensively metabolized in the liver, primarily via CYP450-mediated oxidation to cyclohexanol (via a reactive epoxide intermediate), followed by further oxidation to cyclohexanone and ultimately ring-opening to adipic acid (hexanedioic acid). The elimination half-life is short (approximately 2-4 hours). The primary route of excretion is via urine (60-80% of the dose within 48 hours) as oxidized metabolites (adipic acid, cyclohexanone, cyclohexanol conjugates) and via bile into feces (20-30%) as parent drug and glutathione conjugates. Only a small fraction (<5%) is excreted unchanged in urine. The deuterated internal standard is essential for accurate quantification of the parent compound in these studies.
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| Toxicity/Toxicokinetics |
Bromocyclohexane-d11 is a research-grade stable isotope-labeled compound, not a pharmaceutical drug. Its unlabeled parent, bromocyclohexane, has low to moderate acute toxicity. The oral LD₅0 in rats is approximately 1,600-2,000 mg/kg, indicating low toxicity. Inhalation or ingestion may cause irritation of the respiratory tract, eyes, and skin. There is limited data on chronic or carcinogenic effects. The primary hazard associated with bromocyclohexane is its classification as a lachrymator (tear-producing agent) and skin irritant. In animal studies, high intraperitoneal doses (500-1,000 mg/kg) have been associated with central nervous system depression (ataxia, lethargy) and liver weight increase, but no significant histopathological changes. The labeled Bromocyclohexane-d11 is presumed to have the same safety profile. For laboratory handling: avoid inhalation, skin contact, and eye exposure. Use appropriate PPE (gloves, safety goggles, lab coat). Work in a well-ventilated area (fume hood) to prevent accumulation of vapors. Store at -20degC or 2-8degC in a tightly sealed container, away from strong oxidizing agents. For research use only, not for diagnostic or therapeutic applications.
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| References | |
| Additional Infomation |
Bromocyclohexane-d11 is the fully deuterium-labeled version of bromocyclohexane (cyclohexyl bromide), where all eleven hydrogen atoms are replaced with deuterium (2H). It is intended for research use as an internal standard for the accurate quantification of bromocyclohexane and its derivatives by GC-MS, and as a tracer in mechanistic organic chemistry (kinetic isotope effects, KIE) and chemical reaction studies. In synthetic chemistry, bromocyclohexane is a common starting material for the preparation of cyclohexylmagnesium bromide (Grignard reagent) and other organometallic compounds used in alkylation reactions. Its high degree of deuteration (≥98 atom % D) ensures minimal isotopic impurity, providing a clean mass shift of +11 Da for sensitive analytical methods. Bromocyclohexane-d11 is also a valuable tool for studying metabolic pathways of cycloalkyl halides in biotransformation research. For research use only, not for human consumption.
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| Molecular Formula |
C6D11BR
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| Molecular Weight |
174.12
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| Exact Mass |
173.073
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| CAS # |
35558-49-7
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| PubChem CID |
16213231
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
161.1±9.0 °C at 760 mmHg
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| Flash Point |
62.8±0.0 °C
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| Vapour Pressure |
3.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.499
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| LogP |
3.21
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
0
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
7
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| Complexity |
46.1
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C1(C([2H])([2H])C([2H])([2H])C([2H])(Br)C([2H])([2H])C1([2H])[2H])[2H]
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| InChi Key |
AQNQQHJNRPDOQV-KAFHOZLVSA-N
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| InChi Code |
InChI=1S/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2/i1D2,2D2,3D2,4D2,5D2,6D
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| Chemical Name |
1-bromo-1,2,2,3,3,4,4,5,5,6,6-undecadeuteriocyclohexane
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ≥ 100 mg/mL (574.32 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.7432 mL | 28.7158 mL | 57.4317 mL | |
| 5 mM | 1.1486 mL | 5.7432 mL | 11.4863 mL | |
| 10 mM | 0.5743 mL | 2.8716 mL | 5.7432 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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