DIMETHYLAMINOETHYLPARA-CHLOROPHENOXYACETATE
meclofenoxate
CAS: 51-68-3
Molecular Formula: C12H16ClNO3
DIMETHYLAMINOETHYLPARA-CHLOROPHENOXYACETATE - Names and Identifiers
| Name | meclofenoxate |
| Synonyms | MECLOFENOXATE meclofenoxate Meclofenoxatum Centrophenoxine, Meclofenoxate DIMETHYLAMINOETHYLPARA-CHLOROPHENOXYACETATE 2-dimethylaminoethyl 4-chlorophenoxyacetate 2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate 2-(DIMETHYLAMINO)ETHYLPARA-CHLOROPHENOXYACETATE 2-(4-chlorophenoxy)acetic acid 2-dimethylaminoethyl ester (4-chlorophenoxy)-acetic acid 2-(dimethylamino)ethyl ester |
| CAS | 51-68-3 |
| EINECS | 200-116-3 |
| InChI | InChI=1/C12H16ClNO3/c1-14(2)7-8-16-12(15)9-17-11-5-3-10(13)4-6-11/h3-6H,7-9H2,1-2H3 |
DIMETHYLAMINOETHYLPARA-CHLOROPHENOXYACETATE - Physico-chemical Properties
| Molecular Formula | C12H16ClNO3 |
| Molar Mass | 257.71 |
| Density | 1.2038 (rough estimate) |
| Melting Point | 138-140 °C |
| Boling Point | 180 °C(Press: 9-10 Torr) |
| Flash Point | 163°C |
| Vapor Presure | 5.95E-05mmHg at 25°C |
| pKa | 8.17±0.28(Predicted) |
| Refractive Index | 1.5200 (estimate) |
| Physical and Chemical Properties | The commodity of this product is hydrochloride (C12H16CINO3 · HCL,[3685-85-5]), also known as Lucidril, bronal, etc., is a white crystalline powder with a melting point of 135-139 ℃. Very soluble in water, insoluble in ether, benzene and chloroform. Sour bitter, moisture-prone to decomposition and failure. |
DIMETHYLAMINOETHYLPARA-CHLOROPHENOXYACETATE - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| meclofenoxate effect | meclofenoxate can promote the redox process of brain cells, increase the utilization of carbohydrate compounds, and regulate the metabolism of nerve cells. It has an exciting effect on the central nervous system in an inhibited state, which can improve the function of the central nervous system, invigorate the spirit, and eliminate fatigue. The effect appears slowly and often requires repeated medication. It is suitable for traumatic coma, cerebral arteriosclerosis or consciousness disorder caused by epilepsy, neonatal hypoxia, children's mental retardation, pediatric enuresis, alcoholism and carbon monoxide toxic mental diseases. Fig. 1 is the structural formula |
| precautions | 1. the aqueous solution of this product is easy to hydrolyze and should be prepared before use. 2. Do not use |
| usage and dosage | oral administration: adults 0.1~0.3g per time, 0.3~0.9g per day; Children 100 mg each time, 2~3 times a day. Intramuscular injection or intravenous drip: 0.25g for adults, 1~3 times a day. Dissolve in 250~500 ml of 5% glucose solution for intravenous drip. Newborns can be injected into umbilical vein: 60~100 mg for children twice a day. |
| adverse reactions | occasionally can cause excitement, insomnia, blood pressure changes, vascular pain or burnout. |
| Use | Chloroester is a stimulant for the central nervous system. It mainly acts on the cerebral cortex, promotes the redox of brain cells, increases the utilization of sugar, can regulate the metabolism of nerve cells, and promotes the excitement of the nervous system in the inhibited state. It is an effective drug to stimulate the spirit and inhibit fatigue. Its effect is slower, and the effect is more significant after repeated use. Its efficacy and duration are better than ephedrine in sheep. It is suitable for consciousness disorder, extra-cranial coma, neonatal hypoxia, enuresis in children, alcoholism, mental disorders and some other neurological diseases. The oral LD50 of mice is 1750mg/kg. |
| Production method | It is prepared by esterification of p-chlorophenoxyacetic acid (see 09610) and dimethylaminoethanol. Add p-chlorophenoxyacetic acid, dimethylaminoethanol, m-xylene and p-toluenesulfonic acid to the reaction pot, stir and heat, and dehydrate at 145 ℃ until it is steamed out without water drops. Cold to 40 ℃, add activated carbon to decolorise. Then cool to about 5 ℃, pass in dry hydrogen chloride gas, first precipitate yellow oil, which is excessive dimethylamine ethanol hydrochloride, and then precipitate chlorine ester to wake up hydrochloride until the solution is strongly acidic. The lower layer of oil is separated, the upper layer of white crystals is frozen and filtered, and the crystals are washed with xylene to obtain crude products. Finally, the finished product is obtained by recrystallization of isopropyl alcohol and decolorization of activated carbon. Another preparation method is to mix the chloroform solution of p-chlorophenoxyacetic acid and equimolar triethylamine, and add phosphorus oxychloride dropwise under stirring. After adding, continue the reaction for 1 hour, then add equimolar dimethylamine ethanol, react at 25 ℃ for 3 hours, add water and stir evenly, and alkalize with sodium carbonate solution. The chloroform layer is separated, the chloroform is recovered after drying, and the obtained oil is added to isopropyl alcohol containing hydrogen chloride to precipitate crystals. After recrystallization with isopropanol, p-chlorophenoxyacetic acid dimethylaminoethyl ester hydrochloride with melting point of 135-137 ℃ was obtained with 54% yield. |
Last Update：2024-04-10 22:29:15
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