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Name |
Metoclopramide |
EINECS | 206-662-9 |
CAS No. | 364-62-5 | Density | 1.162 g/cm3 |
PSA | 67.59000 | LogP | 2.97450 |
Solubility | N/A | Melting Point |
146-148 °C |
Formula | C14H22ClN3O2 | Boiling Point | 418.7 °C at 760 mmHg |
Molecular Weight | 299.801 | Flash Point | 207 °C |
Transport Information | N/A | Appearance | N/A |
Safety | 36/37 | Risk Codes | 22-64 |
Molecular Structure | Hazard Symbols | Xn | |
Synonyms |
o-Anisamide,4-amino-5-chloro-N-[2-(diethylamino)ethyl]- (7CI,8CI);2-Methoxy-4-amino-5-chloro-N,N-dimethylaminoethylbenzamide;2-Methoxy-5-chloroprocainamide;N-[2-(Diethylamino)ethyl]-4-amino-5-chloro-2-methoxybenzamide;Plasil;Primperan;Regla;4-Amino-5-chloro-2-methoxy-N-(b-diethylaminoethyl)benzamide;4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide;4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-o-anisamide;5-Chloro-2-methoxyprocainamide;Clopromate;DEL 1267;Draclamid;Eucil;Gastrese;Gastro-Timelets;Gastromax;Gastrosil;Gastrotem;MCP-ratiopharm;Macperan;Maxeran;Meclopran;Metamide;Metoclol;Metramid;Moriperan;N-(2-Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide;N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide; |
Article Data | 53 |
4-amino-5-chloro-2-methoxybenzoic acid
N,N-diethylethylenediamine
metoclopramide
Conditions | Yield |
---|---|
With borane-ammonia complex In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux; | 88% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In methanol; dichloromethane | 65% |
methyl 2-methoxy 4-acetamido 5-chloro benzoate
N,N-diethylethylenediamine
metoclopramide
Conditions | Yield |
---|---|
With sodium hydroxide; acetic acid 1.) 90-95 deg C, 4 h, 2.) water, heating; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
In tetrahydrofuran for 3h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 1 h / 0 °C 2: tetrahydrofuran / 3 h / Ambient temperature View Scheme |
Methyl 4-amino-2-methoxybenzoate
metoclopramide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2O / 1.) room temp., 30 min., 2.) 60-70 deg C, 1 h 2: aq. sodium hypochlorite / 1 h 3: 1.) glacial acetic acid, 2.) NaOH / 1.) 90-95 deg C, 4 h, 2.) water, heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. sodium hypochlorite / 1 h 2: 1.) glacial acetic acid, 2.) NaOH / 1.) 90-95 deg C, 4 h, 2.) water, heating View Scheme |
4-amino-5-chloro-2-methoxybenzoic acid
N,N-diethylethylenediamine
1-methanesulfonyloxy-1,2,3-benzotriazole
metoclopramide
Conditions | Yield |
---|---|
With sodium hydroxide; triethylamine In chloroform; water |
C17H27ClN4O2
metoclopramide
Conditions | Yield |
---|---|
Stage #1: C17H27ClN4O2 With ethylenediamine In ethanol for 10h; Reflux; Stage #2: With water | 2.32 g |
carbon monoxide
2-chloro-4-iodo-5-methoxyaniline
N,N-diethylethylenediamine
metoclopramide
Conditions | Yield |
---|---|
With triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 80℃; Inert atmosphere; Sealed chamber; | 63.2 mg |
The CAS registry number of Metoclopramide is 364-62-5. With the EINECS registry number 206-662-9, its systematic name is 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide. In addition, the molecular formula is C14H22ClN3O2. What's more, it should be stored in sealed container, and put in a cool and dry place.
Physical properties about this chemical are: (1)ACD/LogP: 2.22; (2)ACD/LogD (pH 5.5): -0.85; (3)ACD/LogD (pH 7.4): 0.04; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 2.54; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 8; (11)Polar Surface Area: 36.02 Å2; (12)Index of Refraction: 1.553; (13)Molar Refractivity: 82.57 cm3; (14)Molar Volume: 257.8 cm3; (15)Polarizability: 32.73 ×10-24cm3; (16)Surface Tension: 43.8 dyne/cm; (17)Density: 1.162 g/cm3; (18)Flash Point: 207 °C; (19)Enthalpy of Vaporization: 67.23 kJ/mol; (20)Boiling Point: 418.7 °C at 760 mmHg; (21)Vapour Pressure: 3.22E-07 mmHg at 25°C.
Preparation of Metoclopramide: It can start with the esterification, acylation and methylation of p-aminosalicylic acid, and gives methyl p-acetamido-methoxybenzoate. The methyl p-acetamido-methoxybenzoate can go through chlorination, amination and hydrolysis to give the desired product.
Uses of Metoclopramide: it can be used to get metoclopramide N-oxide. This reaction will need reagent m-chloroperbenzoic acid and solvent CH2Cl2. The reaction time is 20 minutes with ambient temperature.
You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(c(OC)cc1N)C(=O)NCCN(CC)CC
(2)Std. InChI: InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
(3)Std. InChIKey: TTWJBBZEZQICBI-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | intravenous | 2mg/kg/1D-C (2mg/kg) | BEHAVIORAL: EXCITEMENT | Journal of Pediatrics. Vol. 104, Pg. 138, 1984. |
child | TDLo | oral | 900ug/kg (0.9mg/kg) | SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Archives of Disease in Childhood. Vol. 55, Pg. 310, 1980. |
infant | TDLo | oral | 3mg/kg/9H-I (3mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ATAXIA | Pediatric Emergency Care. Vol. 14, Pg. 39, 1998. |
man | TDLo | intravenous | 14ug/kg (0.014mg/kg) | VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | Annals of Internal Medicine. Vol. 104, Pg. 125, 1986. |
man | TDLo | oral | 111mg/kg/37W- (111mg/kg) | PERIPHERAL NERVE AND SENSATION: FASCICULATIONS | Japanese Journal of Medicine. Vol. 23, Pg. 152, 1984. |
man | TDLo | oral | 632mg/kg/59D- (632mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TOXIC PSYCHOSIS BEHAVIORAL: EXCITEMENT | Journal of Clinical Psychiatry. Vol. 48, Pg. 38, 1987. |
mouse | LD50 | intraperitoneal | 96mg/kg (96mg/kg) | Drugs in Japan Vol. 6, Pg. 838, 1982. | |
mouse | LD50 | intravenous | 33mg/kg (33mg/kg) | Drugs in Japan Vol. 6, Pg. 838, 1982. | |
mouse | LD50 | oral | 270mg/kg (270mg/kg) | Drugs in Japan Vol. 6, Pg. 838, 1982. | |
mouse | LD50 | subcutaneous | 190mg/kg (190mg/kg) | Drugs in Japan Vol. 6, Pg. 838, 1982. | |
rabbit | LD50 | intravenous | 30mg/kg (30mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. | |
rat | LD50 | intraperitoneal | 114mg/kg (114mg/kg) | Drugs in Japan Vol. 6, Pg. 838, 1982. | |
rat | LD50 | intravenous | 50mg/kg (50mg/kg) | Bollettino Chimico Farmaceutico. Vol. 115, Pg. 649, 1976. | |
rat | LD50 | oral | 750mg/kg (750mg/kg) | Drugs in Japan Vol. 6, Pg. 838, 1982. | |
rat | LD50 | subcutaneous | 340mg/kg (340mg/kg) | Drugs in Japan Vol. 6, Pg. 838, 1982. | |
women | TDLo | intravenous | 2400ug/kg (2.4mg/kg) | VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | New England Journal of Medicine. Vol. 307, Pg. 1346, 1982. |
women | TDLo | oral | 3600ug/kg/6D- (3.6mg/kg) | BEHAVIORAL: TREMOR GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Annals of Internal Medicine. Vol. 97, Pg. 621, 1982. |