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Trimethylammonium chloride is a non-competitive inhibitor of acetylcholinesterase (AChE), the enzyme responsible for hydrolyzing the neurotransmitter acetylcholine in the synaptic cleft. By inhibiting AChE, the compound increases acetylcholine levels in the central and peripheral nervous systems. It is also an endogenous metabolite that inhibits deacetylation reactions. The compound does not have a specific drug receptor but acts as a pharmacological tool to study cholinergic signaling and enzyme inhibition. As a metabolite of choline, it targets enzymes involved in choline metabolism, including choline dehydrogenase and betaine aldehyde dehydrogenase.
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| ln Vitro |
In vitro, Trimethylammonium chloride acts as a non-competitive inhibitor of acetylcholinesterase (AChE) with an IC₅0 that can be measured using the Ellman method (see non-cellular assays below). At concentrations of 1-100 mM, the compound inhibits AChE activity in a dose-dependent manner. It also inhibits deacetylation reactions, suggesting potential activity against histone deacetylases (HDACs) or other deacetylases. As an endogenous metabolite, it is used as a standard in analytical chemistry for the quantification of trimethylamine in biological samples. No other direct cellular activities have been reported.
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| ln Vivo |
In vivo, Trimethylammonium chloride is an endogenous metabolite present in humans and animals. It is produced from dietary choline by gut microbiota; elevated levels are associated with trimethylaminuria (fish odor syndrome), a genetic disorder caused by deficiency of flavin-containing monooxygenase 3 (FMO3). The compound is also associated with high-dose choline intake. No significant pharmacological activity as a therapeutic has been reported for this compound. It is not typically used in in vivo drug studies but serves as a biomarker for gut microbiota activity and choline metabolism. The compound is primarily a research tool and analytical standard.
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| Enzyme Assay |
For non-cellular assays (enzyme inhibition), acetylcholinesterase (AChE) activity is measured using the Ellman method. AChE (from electric eel or human recombinant, 0.5 U/mL) is incubated with Trimethylammonium chloride (0.1-100 mM) in 100 uL of 50 mM phosphate buffer (pH 7.4) for 10 minutes at 25degC. Then, 50 uL of 5,5′-dithiobis(2-nitrobenzoic acid) (DTNB, 1 mg/mL) and 50 uL of acetylthiocholine iodide (0.5 mM) are added. The reaction proceeds for 5-10 minutes, and absorbance at 412 nm is measured. The percent inhibition is calculated relative to a control without inhibitor. The IC₅0 value is determined from dose-response curves. For deacetylation inhibition assays, a fluorometric HDAC activity assay kit using an acetylated peptide substrate can be used. For analytical quantification (LC-MS/MS), a calibration curve is prepared in human plasma or urine (0.1-1000 ng/mL) with the deuterated internal standard (trimethylammonium chloride-d9).
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| Cell Assay |
For cell-based assays, neuronal cell lines (e.g., SH-SY5Y, PC12 cells) or hepatocytes (HepG2 cells) are seeded in 6-well plates (1×10⁶ cells/well) in DMEM with 10% FBS. Cells are treated with Trimethylammonium chloride (1-50 mM) for 24-48 hours. Cell viability is assessed by MTT or Alamar Blue assays. For AChE activity measurements, cell lysates are prepared in lysis buffer, and AChE activity is measured using the Ellman method as described above. For mechanistic studies of trimethylaminuria, hepatocytes are treated with choline (10-100 uM) and the production of trimethylamine is measured by LC-MS/MS. Trimethylammonium chloride is used as a standard for quantification. For toxicity studies, LDH release and caspase-3/7 activity are measured.
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| Animal Protocol |
For in vivo animal experiments, rodent models are used to study choline metabolism and trimethylamine production. Mice are fed a high-choline diet or administered choline (10-50 mg/kg, oral) to induce trimethylamine production. Blood, urine, and fecal samples are collected at multiple time points. Trimethylammonium chloride levels are measured by LC-MS/MS using the deuterated internal standard (trimethylammonium chloride-d9). For trimethylaminuria models, FMO3 knockout mice are used, and trimethylamine levels in urine are measured. For neurodegenerative disease models, the compound is not typically administered directly; instead, the effects of AChE inhibition by trimethylammonium chloride are studied indirectly. Standard safety precautions for handling toxic amines must be observed.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
The experimental results of trimethylamine hydrochloride indicate that trimethylamine is an intermediate in the conversion of choline to dimethylamine. Trimethylammonium chloride has a molecular weight of 95.57, a melting point of 283-287degC (dec.), and appears as a white to off-white crystalline powder. It is highly soluble in water (approximately 1 g/mL) and soluble in ethanol. The compound is hygroscopic and should be stored in a tightly sealed container at room temperature, protected from moisture. The pKa of trimethylammonium ion is approximately 9.8. The compound is stable under normal storage conditions but may decompose at high temperatures. It has a characteristic fishy amine odor, especially when wet or heated. The hydrochloride salt form is more stable and less volatile than the free amine. For analytical formulations, the compound is often stored as a solution in water or acetonitrile. |
| Toxicity/Toxicokinetics |
Trimethylammonium chloride has low acute toxicity. The oral LD₅0 in rats is approximately 500-1000 mg/kg. At high doses (≥500 mg/kg), the compound may cause cholinergic side effects due to AChE inhibition, including salivation, lacrimation, urination, defecation, and tremors. Skin contact may cause irritation. Inhalation of the dust may cause respiratory tract irritation. Standard laboratory safety precautions for handling amines should be followed, including the use of PPE (gloves, goggles, lab coat) and working in a fume hood. The compound is not classified as a carcinogen. When heated to decomposition, it may emit toxic fumes of HCl and nitrogen oxides. In case of contact, wash skin and eyes with plenty of water.
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| References | |
| Additional Infomation |
Trimethylamine hydrochloride is a hydrochloride salt formed by the reaction of equimolar amounts of trimethylamine and hydrogen chloride. It contains trimethylammonium.
Trimethylammonium chloride is a research compound and analytical standard, not an approved drug. It has not undergone clinical trials for therapeutic use. Its primary applications include use as a non-competitive inhibitor of acetylcholinesterase for studying cholinergic signaling in neurobiology and pharmacology, as an endogenous metabolite standard for LC-MS analysis of trimethylamine in clinical and research settings (e.g., for trimethylaminuria diagnosis, assessment of gut microbiota activity, and choline metabolism studies), and as a deacetylation inhibitor for biochemical research. The compound is also used in the synthesis of quaternary ammonium compounds and as a phase transfer catalyst. Available for research use only. Not intended for diagnostic or therapeutic applications. |
| Molecular Formula |
C3H10CLN
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| Molecular Weight |
95.57
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| Exact Mass |
95.05
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| CAS # |
593-81-7
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| Related CAS # |
Trimethylammonium chloride-d9;18856-86-5;Trimethylammonium chloride-13C3,d9;2483824-12-8;Trimethylammonium chloride-d10;107766-37-0;Trimethylammonium chloride-15N;108451-51-0;Trimethylammonium chloride-d6;347840-14-6
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| PubChem CID |
10313079
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| Appearance |
White to off-white solid powder
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| Density |
0.692g/cm3
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| Boiling Point |
2.8ºC at 760 mmHg
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| Melting Point |
277.5 °C
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| LogP |
0.979
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
5
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| Complexity |
8
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CN(C)C.Cl
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| InChi Key |
SZYJELPVAFJOGJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C3H9N.ClH/c1-4(2)3;/h1-3H3;1H
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| Chemical Name |
N,N-dimethylmethanamine;hydrochloride
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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: 41.67 mg/mL (436.02 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 | 10.4635 mL | 52.3177 mL | 104.6353 mL | |
| 5 mM | 2.0927 mL | 10.4635 mL | 20.9271 mL | |
| 10 mM | 1.0464 mL | 5.2318 mL | 10.4635 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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