Propargylcholine bromide is a choline analog containing a terminal propargyl group that can be incorporated into and labeled by all classes of choline phospholipids (choline-containing phospholipids) like phosphatidylcholine and sphingomyelin. . Propargylcholine bromide-labeled phospholipid molecules can be visualized in cells with high sensitivity and spatial resolution. Propargylcholine bromide can be used as a molecular tool to study the biochemical and metabolic processes of choline phospholipids in cells. Propargylcholine (bromide) is a reagent for click chemistry. It has Alkyne groups and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing Azide groups.

Physicochemical Properties

Molecular Formula	C7H14BRNO
Molecular Weight	208.1
Exact Mass	207.025
Elemental Analysis	C, 40.40; H, 6.78; Br, 38.40; N, 6.73; O, 7.69
CAS #	111755-76-1
Related CAS #	111755-76-1 (bromide);
PubChem CID	15029189
Appearance	Solid powder
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Heavy Atom Count	10
Complexity	120
Defined Atom Stereocenter Count	0
SMILES	[Br-].OCC[N+](C)(C)CC#C
InChi Key	CDMUCZDUIQLBJB-UHFFFAOYSA-M
InChi Code	InChI=1S/C7H14NO.BrH/c1-4-5-8(2,3)6-7-9;/h1,9H,5-7H2,2-3H3;1H/q+1;/p-1
Chemical Name	2-hydroxyethyl-dimethyl-prop-2-ynylazanium;bromide
Synonyms	Propargylcholine ; Propargylcholine bromide;
HS Tariff Code	2934.99.9001
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, 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)

Biological Activity

ln Vitro	After being added to NIH 3T3 cells at a concentration of 10, 50 µM for 24 hours, propargylcholine bromide (fixed and stained with Alexa568-azide) exhibited robust staining in a concentration-dependent manner [1]. fluorescent imaging [1]
ln Vivo	In rhesus monkeys, propargylcholine bromide (P-Cho; 3.5–4.0 mg/kg; intraperitoneally; once daily for 6 days) is well integrated into freshly generated myelin within 1 week of injection and is there for over 6 weeks [2].
Cell Assay	Immunofluorescence[1] Cell Types: NIH 3T3 Cell Tested Concentrations: 10, 50 µM Incubation Duration: 24 hrs (hours) Experimental Results: Shows strong staining, the intensity of which is proportional to the concentration of propargylcholine bromide added.
References	[1]. Jao CY, et al. Metabolic labeling and direct imaging of choline phospholipids in vivo. Proc Natl Acad Sci U S A. 2009 Sep 8;106(36):15332-7. [2]. Karen R. Bottenfield, et al. Optimization of Propargylcholine to Label Newly Synthesized Myelin in the Rhesus Monkey Brain. FASEB J. 2020, 34(S1): 1-1.

Solubility Data

Solubility (In Vitro)

H2O : ~125 mg/mL (~600.67 mM) DMSO : ~125 mg/mL (~600.67 mM)

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 (e.g. IP/IV/IM/SC) 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). 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) 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). 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 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.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.8054 mL	24.0269 mL	48.0538 mL
	5 mM	0.9611 mL	4.8054 mL	9.6108 mL
	10 mM	0.4805 mL	2.4027 mL	4.8054 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.