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Carpronium chloride

Alias: Actinomin chloride
Actinomin is a parasympathetic stimulant with a chemical structure similar to acetylcholine.
Carpronium chloride
Carpronium chloride Chemical Structure CAS No.: 13254-33-6
Product category: ChE
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Carpronium (Actinomin) chloride is a parasympathetic stimulant with a chemical structure similar to acetylcholine. Carpronium chloride has cholinergic and local vasodilatory effects, promoting hair growth by dilating local blood vessels, stimulating the transition of hair from the telogen to the anagen phase, and stimulating parasympathetic nerve activity. Carpronium chloride can be used in immunological studies of alopecia areata, dry seborrheic dermatitis, and vitiligo.
Carpronium chloride (Actinomin chloride) is a parasympathetic nerve stimulant with chemical structure similar to acetylcholine. It is a quaternary ammonium compound that functions as a cholinergic agonist and local vasodilator. The compound is used for research on alopecia areata, seborrhea sicca, and vitiligo due to its hair growth-promoting effects. Carpronium chloride works by dilating local blood vessels, stimulating the transition from telogen (resting) phase to anagen (growth) phase of hair follicles, and enhancing parasympathetic nerve activity. It is applied topically or studied in microvascular models.
Biological Activity I Assay Protocols (From Reference)
Targets
Carpronium chloride targets muscarinic cholinergic receptors as a muscarinic agonist. It binds to these receptors, mimicking acetylcholine, and activates parasympathetic nerve pathways. This activation leads to local vasodilation via vascular smooth muscle relaxation in the microcirculation. The compound also influences gene expression related to cholinergic signaling. Its primary mechanism involves cholinergic stimulation and local vasodilatory activity. Additionally, carpronium chloride acts as a phase transfer catalyst in organic synthesis due to its quaternary ammonium structure, contributing to stability and effectiveness in various formulations.
ln Vitro
In vivo studies indicate carpronium chloride achieves dilatation of vascular smooth muscle in the microcirculation of rat mesenteric arterioles. Topical application causes arteriolar vasodilation and increased blood flow. The vasodilatory effect is approximately 10 times more potent than acetylcholine on skin microvessels. It promotes hair growth by improving local blood circulation, nutrient delivery, prolonging anagen phase, and reducing inflammation. The compound also stimulates the transition from telogen to anagen phase of hair follicles. Studies show it significantly increases absorption of minoxidil in hair follicles when used as pre-treatment.
ln Vivo
In vivo rat studies using intravital videomicroscopy demonstrated that carpronium chloride applied topically induced arteriolar vasodilation and increased microvascular blood flow in rat mesentery, while no significant change occurred in mean systemic blood pressure, indicating localized action without systemic vasomotor effects. The compound also stimulates parasympathetic nerve activity and promotes hair follicle transition from telogen to anagen phase in animal models of alopecia. Formulations combining carpronium chloride with minoxidil produced better hair growth outcomes than minoxidil alone.
Enzyme Assay
Not applicable as this compound primarily functions in cell-based and in vivo systems. For cholinergic receptor binding studies, prepare carpronium chloride at 0.01-100 microM in PBS (pH 7.4). Incubate with membrane preparations from rat brain (100 microg protein) containing muscarinic receptors in 50 mM Tris-HCl buffer with 1 mM EDTA for 60 min at 25degC. Use [3H]N-methylscopolamine (1 nM) as radioligand. Measure bound radioactivity by filtration through GF/B filters. Non-specific binding determined with 10 microM atropine. Calculate Ki by competitive binding curve fitting.
Cell Assay
For in vitro cell assays, culture human dermal papilla cells or keratinocytes in DMEM with 10% FBS at 37degC, 5% CO2. Seed 1×10⁴ cells per well in 96-well plates, incubate overnight. Treat with carpronium chloride at 0.1-500 microM in triplicate for 24-72 h. Assess cell viability by MTT assay (0.5 mg/mL, 4 h, then solubilize in DMSO, read at 570 nm). For proliferation, use EdU incorporation (10 microM EdU for 2 h) followed by flow cytometry. For vasodilation assays, use isolated rat aortic rings mounted in organ baths with Krebs buffer, pre-contracted with phenylephrine, and add carpronium chloride (1-300 microM) to measure relaxation.
Animal Protocol
For in vivo microvascular studies using intravital videomicroscopy, male Wistar rats (250-300 g) are anesthetized with pentobarbital (50 mg/kg IP). The mesentery is exteriorized and placed on a transparent stage. Carpronium chloride is applied topically at concentrations of 0.01-1% in saline. Arteriolar diameter is measured using videomicroscopy with image analysis software at baseline and every 5 min for 30 min. Blood flow velocity is measured using dual photodiode cross-correlation. For hair growth studies, topical application of 0.5% carpronium chloride solution is applied to shaved dorsal skin of mice once daily for 4 weeks. Hair regrowth is assessed by visual scoring and histological analysis.
ADME/Pharmacokinetics
No detailed PK studies available for carpronium chloride as it is a topical agent not intended for systemic absorption. Based on its quaternary ammonium structure (a permanently charged cation), carpronium chloride has very low lipophilicity and poor ability to cross biological membranes, including skin barrier and intestinal epithelium. Topical application results in local effects in the dermis and microvasculature with minimal systemic exposure. When absorbed, it likely undergoes rapid renal excretion unchanged due to its polar, water-soluble nature. Oral bioavailability is negligible. The compound is not metabolized significantly. Half-life in plasma not determined. No tissue accumulation expected.
Toxicity/Toxicokinetics
Local application is generally well-tolerated. In clinical use as a topical hair growth treatment, carpronium chloride may cause mild local skin irritation, redness, or itching at the application site in some individuals. No systemic toxicities have been reported due to minimal absorption through skin. In rat studies, no significant changes in mean systemic blood pressure were observed during topical application, indicating lack of systemic cardiovascular effects. No carcinogenicity, genotoxicity, or reproductive toxicity data available as compound is primarily used in cosmetic and topical research applications. Contraindicated in individuals with known hypersensitivity.
References

[1]. Cholinergic crisis caused by ingesting topical carpronium chloride solution: A case report. Am J Emerg Med. 2021;50:811.e1-811.e2.

[2]. Seventeen cases of alopecia areata: combination of SADBE topical immunotherapy with other therapies. J Dermatol. 2002;29(10):661-664.

Additional Infomation
Carpronium Chloride is the chloride of carpronium. It is a hair growth agent used to treat hair loss. It has vasodilatory and muscarinic receptor agonist effects. It is a chloride, methyl ester, and quaternary ammonium salt. It contains a carpronium group.
See also: Carpronium (containing the active moiety).
Carpronium chloride is also known as Actinomin chloride. CAS: 13254-33-6. Molecular formula: C8H18ClNO2. Molecular weight: 195.69. Purity: typically >99%. IUPAC name: 4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium chloride. Appearance: white crystalline powder. Soluble in water and organic solvents. Used as a cholinergic agonist for alopecia research and as a phase transfer catalyst. Marketed in Japan and other Asian countries as topical hair growth solution (e.g., Furozin Solution 5%). Also available as monohydrate form. For research use only, not for clinical treatment without regulatory approval. Storage: room temperature, protected from moisture.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H18CLNO2
Molecular Weight
195.69
Exact Mass
195.103
CAS #
13254-33-6
Related CAS #
14075-13-9 (Parent)
PubChem CID
25804
Appearance
White to off-white solid powder
Hydrogen Bond Donor Count
0
Rotatable Bond Count
5
Heavy Atom Count
12
Complexity
127
Defined Atom Stereocenter Count
0
SMILES
C[N+](C)(C)CCCC(=O)OC.[Cl-]
InChi Key
RZMKWKZIJJNSLQ-UHFFFAOYSA-M
InChi Code
InChI=1S/C8H18NO2.ClH/c1-9(2,3)7-5-6-8(10)11-4;/h5-7H2,1-4H3;1H/q+1;/p-1
Chemical Name
(4-methoxy-4-oxobutyl)-trimethylazanium chloride
Synonyms
Actinomin chloride
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~200 mg/mL (~1022.02 mM; with sonication)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 5 mg/mL (25.55 mM)(saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one)),clear solution.
For example, if 1 mL of working solution is to be prepared, you can Add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix thoroughly. Then add 50 μL of Tween-80 to the above system and mix thoroughly. Finally, add 450 μL of physiological saline to bring the volume to 1 mL. Preparation of physiological saline: Dissolve 0.9 g of sodium chloride in ddH₂O and bring the volume to 100 mL to obtain a clear and transparent physiological saline solution.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 5 mg/mL (25.55 mM)(saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one)),clear solution.
For example, if 1 mL of working solution is to be prepared, you can Add 100 μL of 50.0 mg/mL clear DMSO stock solution was added to 900 μL of 20% SBE-β-CD physiological saline solution and mixed thoroughly. 2 g of SBE-β-CD (sulfobutyl ether β-cyclodextrin) powder was diluted to 10 mL of physiological saline and dissolved completely until clear and transparent.
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.

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Solubility in Formulation 3: ≥ 5 mg/mL (25.55 mM)(saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one)),clear solution.
For example, if 1 mL of working solution is to be prepared, you can Add 100 μL of 50.0 mg/mL clarified DMSO stock solution to 900 μL of corn oil and mix well.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.1101 mL 25.5506 mL 51.1012 mL
5 mM 1.0220 mL 5.1101 mL 10.2202 mL
10 mM 0.5110 mL 2.5551 mL 5.1101 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.

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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.
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Clinical Trial Information
Single-blind Comparative Clinical Trial of Topical 5% Carpronium Chloride Solution for Androgenetic Alopecia
CTID: Not Applicable
Phase: Phase 2
Status: Completed
Date: 1986-03-20
Double-blind Controlled Clinical Trial of Topical Carpronium Chloride in Patients With Alopecia Areata
CTID: Not Applicable
Phase: Phase 2
Status: Completed
Date: 1987-01-12
Open-label Long-term Safety and Efficacy Observation of Carpronium Chloride Topical Preparation for Seborrhea Sicca and Vitiligo Vulgaris
CTID: Not Applicable
Phase: Phase 3
Status: Completed
Date: 1987-04-18
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