3685-84-5

Basic information

• Product Name: Meclofenoxate hydrochloride
• Synonyms: (p-chlorophenoxy)aceticacid2-(dimethylamino)ethylesterhydrochloride;235anphydrochloride;acefen;aceticacid,(4-chlorophenoxy)-,2-(dimethylamino)ethylester,hydrochloride;aceticacid,(p-chlorophenoxy)-,2-dimethylaminoethylester,hydrochloride;amipolen;brenal;cellative
• CAS NO: 3685-84-5
• Molecular Formula: C₁₂H₁₆ClNO₃*ClH
• Molecular Weight: 294.17
• EINECS: 222-975-3
• Product Categories: API;Other APIs
• Mol File: 3685-84-5.mol

Chemical Properties

• Melting Point: 133-135°C
• Boiling Point: 345.9 °C at 760 mmHg
• Flash Point: 163 °C
• Appearance: white crystal powder
• Density: 1.3255 (rough estimate)
• Vapor Pressure: 5.95E-05mmHg at 25°C
• Refractive Index: 1.6140 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• Merck: 14,5780
• CAS DataBase Reference: Meclofenoxate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Meclofenoxate hydrochloride(3685-84-5)
• EPA Substance Registry System: Meclofenoxate hydrochloride(3685-84-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• RTECS: AG0440000
• Hazardous Substances Data: 3685-84-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Meclofenoxate hydrochloride is used as a cerebral stimulant for addressing memory decline through aging, dementia, Alzheimer's, brain damage or injuries, and alleviating the symptoms and effects of alcohol or drug abuse. It helps improve cognitive functions by acting as an Acetylcholine precursor, which is crucial for memory and learning.
Used in Agriculture:
Meclofenoxate hydrochloride is used as a plant growth regulator, enhancing the growth and development of plants by modulating their metabolic processes and promoting overall plant health.

Pharmacological action

Meclofenoxate hydrochloride(MecloCl) [CAS,NO:51-68-3], an ester of dimethylethanolamine (DMAE) and 4-chlorophenoxyacetic acid (pCPA), has been shown to improve memory, have a mentally stimulating effect, and improve general cognition. Meclofenoxate hydrochloride is a psychostimulant in the nootropic agent group available in capsule and tablet formulations approved for traumatic cataphora, alcoholic poisoning, anoxia neonatorum, and children's enuresis in China. Although these 2 generic formulations are marketed in China, information regarding their pharmacokinetics and bioequivalence in humans has not been published. Meclofenoxate hydrochloride appears to increase the consolidation of new information into long-term memory. Meclofenoxate does not affect other aspects of remembering. Meclofenoxate is found that significantly more of the subjects receiving meclofenoxate reportes an increased level of mental alertness.

Safety Profile

Poison by intravenous route.Moderately toxic by ingestion and intraperitoneal routes.When heated to decomposition it emits very toxic fumes ofCl??, NOx, and HCl.

InChI:InChI=1/C12H16ClNO3.ClH/c1-14(2)7-8-16-12(15)9-17-11-5-3-10(13)4-6-11;/h3-6H,7-9H2,1-2H3;1H

Synthetic route

2-(N,N-dimethylamino)ethanol (108-01-0) + 4-chlorophenyloxyacetyl chloride (4122-68-3) → meclofenoxate hydrochloride (3685-84-5)

Conditions	Yield
In chloroform	90%
With benzene Behandeln des Reaktionsprodukts mit Chlorwasserstoff in Aether und Aceton;
Stage #1: 2-(N,N-dimethylamino)ethanol; 4-chlorophenyloxyacetyl chloride In dichloromethane at 20℃; Green chemistry; Stage #2: With hydrogenchloride In ethyl acetate Solvent; Green chemistry;	68 g

4-Chlorophenoxyacetic acid (122-88-3) → meclofenoxate hydrochloride (3685-84-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: benzene / Behandeln des Reaktionsprodukts mit Chlorwasserstoff in Aether und Aceton View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / 75 °C 2: chloroform View Scheme

meclofenoxate hydrochloride (3685-84-5) → meclofenoxate (51-68-3)

Conditions	Yield
With triethylamine In chloroform	78%

meclofenoxate hydrochloride (3685-84-5) → 2-(N,N-dimethylamino)ethanol (108-01-0) + 4-Chlorophenoxyacetic acid (122-88-3)

Conditions	Yield
With water In various solvent(s) at 25℃; for 8h; Rate constant; pH=5.5; effect of pH, buffer and human serum albumin concentration on hydrolysis;
With water Product distribution; Ambient temperature; in gastric medium; other medium;

meclofenoxate hydrochloride (3685-84-5) → 4-Chlorophenoxyacetic acid (122-88-3) + 2-(N,N-dimethylamino)ethanol hydrochloride (2498-25-1)

Conditions	Yield
With water at 60℃; for 120h; Kinetics; educt as different commercial film coated tablets; var. temp.s, relative humidities, additives and reaction times;
With buffered to pH 3.9; water at 30℃; Rate constant; in the presence and absence of sodium bisulfite (SBS);
With water at 80℃; under 50 Torr; Rate constant; Kinetics; Mechanism; variation of humidity, temperature and pressure;

meclofenoxate hydrochloride (3685-84-5) → C12H16ClNO4

Conditions	Yield
With potassium permanganate; sodium hydroxide In water at 25 - 30℃;

2,4,5,7-tetra-iodo-3',4',5',6'-tetrachlorofluorescein + meclofenoxate hydrochloride (3685-84-5) → C12H16ClNO3*C20H4Cl4I4O5

Conditions	Yield
In water for 0.133333h; pH=2.6;

meclofenoxate hydrochloride (3685-84-5) → C22H37ClNO3(1+)*Br(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / chloroform 2: acetone / 24 h / 55 °C View Scheme

meclofenoxate hydrochloride (3685-84-5) → C22H37ClNO3(1+)*C8H5Cl2O3(1-)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / chloroform 2: acetone / 24 h / 55 °C 3: sodium hydroxide / water / Heating View Scheme

meclofenoxate hydrochloride (3685-84-5) → C22H37ClNO3(1+)*C9H8ClO3(1-)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / chloroform 2: acetone / 24 h / 55 °C 3: sodium hydroxide / water / Heating View Scheme

meclofenoxate hydrochloride (3685-84-5) → C22H37ClNO3(1+)*C10H10ClO3(1-)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / chloroform 2: acetone / 24 h / 55 °C 3: sodium hydroxide / water / Heating View Scheme

meclofenoxate hydrochloride (3685-84-5) → C22H37ClNO3(1+)*C6H2Cl2NO2(1-)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / chloroform 2: acetone / 24 h / 55 °C 3: sodium hydroxide / water / Heating View Scheme

meclofenoxate hydrochloride (3685-84-5) → C22H37ClNO3(1+)*C8H5Cl2O3(1-)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / chloroform 2: acetone / 24 h / 55 °C 3: sodium hydroxide / water / Heating View Scheme

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 4122-68-3 4-chlorophenyloxyacetyl chloride 
• 122-88-3 4-Chlorophenoxyacetic acid 

Downstream Products

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 122-88-3 4-Chlorophenoxyacetic acid 
• 2498-25-1 2-(N,N-dimethylamino)ethanol hydrochloride 
• 51-68-3 meclofenoxate 

Relevant articles and documents

A meclofenoxate hydrochloride preparation method

The invention discloses a meclofenoxate hydrochloride of the preparation method, comprises the following steps: (A) will acid with thionyl chloride in chlorobenzene acyl chloride reaction, to obtain the chlorophenoxy acetyl chloride; (B) step (A) to get chlorophenoxy acetyl chloride and dimethyl amino ethanol by condensation reaction to obtain the meclofenoxate free alkali; (C) step (B) to obtain the free base of the salt-forming acid salt, thermal insulation and filtering to obtain the hydrochloride. The invention easy availability of raw materials, the reaction temperature is low, the operation is convenient, the crude product of high purity, stable quality, the present invention provides a more easy operation, more environmentally friendly, more economic meclofenoxate hydrochloride synthetic pathway.

Esterquat herbicidal ionic liquids (HILs) with two different herbicides: Evaluation of activity and phytotoxicity

Herbicidal ionic liquids (HILs) constitute a new concept in crop protection products. Their main advantage is the potential to combine the efficiency of traditional herbicides with low vapour pressure and adjustable water solubility which leads to improved environmental safety in the agricultural sector. Among many strategies to obtain new HILs, esterquats seem to be well suited for modification since both the cation and anion may be constituents of herbicides. In the framework of this study 16 new esterquat HILs were synthetized based on standard herbicides: 2,4-D, MCPA, MCPP, 4-CPA, Clopyralid and Dicamba. Germination tests performed on agricultural soil using cornflower indicated the best two HILs. Furthermore, analysis of the toxicological effects of HILs on wheat plants revealed an additional advantage of the two selected HILs. The glutathione (GSH) content and glutathione S-transferase (GST) activity showed a lower oxidative stress level in wheat plants treated with examined HILs, respectively, in comparison to a mixture of reference compounds. Finally the Ames test was applied in order to analyse the mutagenic activity of the two selected HILs.