The study found that CCC (300 mg/L) resulted in a large rise in the biomass of lily leaves and stems, a significant drop in the gibberellic acid (GA) content in lily bulbs, and an increase in indole-3-acetic acid (IAA) content in leaves.

Absorption, Distribution and Excretion
Chlorocholine was determined in four sow milk samples, ranging from 0.4 ng/g to 1.2 ng/g… This study used 15N-CCC to investigate the distribution of chlorocholine chloride (CCC) in eggs. Twelve 37-week-old laying hens were divided into four groups and subjected to three feeding phases. In the first phase (7 days), all hens were fed a CCC-free diet [165 g CP/kg dry matter (DM); 11.58 MJ ME/kg DM]. In the second phase (11 days), four concentrations of 15N-CCC were added to the diets of each group: 0, 5, 50, and 250 ppm. In the third phase (7 days), the CCC-free diet was again administered. Egg samples were collected, and the 15N content in the yolk and albumen was determined. At the end of the second phase, the 15N content in egg yolks of mothers fed diets of 50 ppm and 250 ppm CCC was significantly increased (p < 0.05), and the 15N content in egg whites of mothers fed diets of 250 ppm CCC was also significantly increased. The estimated 15N-CCC residues in egg yolks of mothers fed diets of 5 ppm, 50 ppm, and 250 ppm CCC were 1.71 ppm, 6.64 ppm, and 28.80 ppm, respectively, and the estimated 15N-CCC residues in egg whites were 1.58 ppm, 1.08 ppm, and 4.50 ppm, respectively. Quantitative analysis showed that the residual CCC content in the yolks of eggs fed with 50 ppm and 250 ppm CCC was 0.21–0.93 ppm and 0.93–2.43 ppm, respectively, while the residual CCC content in the egg whites of eggs fed with 250 ppm CCC was 0.40–1.46 ppm. The difference between the CCC content measured in the yolks and whites and the content estimated based on 15N-CCC may be due to the decomposition products of 15N-CCC. Seven days after discontinuing 15N-CCC, the residual 15N-CCC in egg yolks from hens fed diets containing 5 ppm, 50 ppm, and 250 ppm CCC decreased to 0.43 ppm, 2.45 ppm, and 15.59 ppm, respectively, while the residual 15N-CCC in egg whites from hens fed diets containing 250 ppm CCC decreased to 2.46 ppm. The significant increase in 15N content is likely due to greater incorporation of 15N-CCC into the yolk than the albumen during rapid yolk deposition. This study demonstrates that ingested CCC is distributed in a dose-dependent manner in both the yolk and albumen, and that CCC is metabolized in laying hens. However, the dietary CCC levels observed in this study that could lead to detectable CCC levels in eggs are significantly higher than the established maximum residue limits (MRLs) for cereals.
In mammals, 97% of oral CCC is excreted within 24 hours, primarily in its unchanged form.

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Metabolism/Metabolites
This experiment aimed to evaluate the metabolites of choline chloride (CCC) in the eggs and meat of laying hens fed a diet containing (15)N-CCC. Ten brown-shelled laying hens were randomly divided into two groups of five each. One group was fed a diet without (15)N-CCC, while the other group was fed a diet containing 100 ppm (15)N-CCC for 11 days. Egg and meat samples were collected from the laying hens. Egg yolks and egg whites were separated. Chicken breast and femur meat samples were collected. The metabolites of CCC were determined using ion trap electrospray ionization mass spectrometry (ion trap-ESI-MS/MS). The determination of CCC and its metabolites in eggs and meat showed that CCC is metabolized to choline. The corresponding MS/MS spectra were detected at m/z 104 (choline) or 105 ((15)N-choline), while no signal was detected at m/z 122 (CCC) or 123 ((15)N-CCC). These results indicate that CCC is metabolized in laying hen tissues. When 14C-labeled CCC was applied to kohlrabi, cauliflower, or tomato, very little CCC degradation occurred. Its main product is likely choline, which enters the plant. A small amount of the labeled methyl group in choline exists as S-methylmethionine. No degradation occurred when CCC was applied to sugarcane. In alfalfa, CCC metabolism was slow, mainly converting to choline in phosphatidylcholine. After treatment of almond seedlings with labeled CCC, translocation to leaves and roots was observed. 14CO₂ was generated within 2 hours of application. Radioactivity was observed in 17 known amino acids, one unidentified ninhydrin-positive compound, malic acid, citric acid, choline, and 2-chloroethylamine. No microbial degradation occurred when chloromethylcholine was cultured with rumen contents or juices under anaerobic conditions. For more complete metabolite/metabolite data on chloromethylcholine chloride (7 metabolites), please visit the HSDB record page.

[1]. Hydration and ion association of aqueous choline chloride and chlorocholine chloride. Phys Chem Chem Phys. 2019 Jun 7;21(21):10970-10980.

[2]. Chlorocholine chloride and paclobutrazol treatments promote carbohydrate accumulation in bulbs of Lilium Oriental hybrids 'Sorbonne'. J Zhejiang Univ Sci B. 2012 Feb;13(2):136-44.

Chloromethylcholine chloride is a white crystalline solid with a fishy odor. It is used as a plant growth regulator. It is reportedly effective on grains, tomatoes, and peppers. (EPA, 1998)
Chloromethylcholine chloride is an organochloride composed of equal parts chloromethylcholine and chloride ions. It is a gibberellin biosynthesis inhibitor and is used as a plant growth inhibitor to make plant stems thicker, facilitating harvesting of ornamental flowers and cereal crops. It is both a plant growth inhibitor and an agricultural chemical. It is an organochloride and quaternary ammonium salt containing chloromethylcholine.
A plant growth regulator commonly used in ornamental plants.
Mechanism of Action

Literature reports that chloromethylcholine chloride acts on nicotine receptor sites at the neuromuscular junction. The tested substance may act as a depolarizer at this site, leading to muscle excitation followed by muscle weakness. Acute toxicity may cause respiratory arrest. The acute toxicity of chloromethylcholine chloride has also been reported to vary by species, possibly due to differences in the sensitivity of different species to depolarizing neuromuscular blocking agents.

C5H13CL2N

158.0694

157.042

999-81-5

Chlorocholine-d4 chloride;Chlorocholine-d9 chloride;1219257-11-0

13836

White to off-white solid powder

239-243 °C (dec.)(lit.)

0

1

2

8

46.5

0

UHZZMRAGKVHANO-UHFFFAOYSA-M

InChI=1S/C5H13ClN.ClH/c1-7(2,3)5-4-6;/h4-5H2,1-3H3;1H/q+1;/p-1

2-chloroethyl(trimethyl)azanium;chloride

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

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.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*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).

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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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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).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)