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Metoclopramide

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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 Molecular Structure of 364-62-5 (4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide) 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

Metoclopramide Synthetic route

7206-70-4

4-amino-5-chloro-2-methoxybenzoic acid

100-36-7

N,N-diethylethylenediamine

364-62-5

metoclopramide

Conditions
ConditionsYield
With borane-ammonia complex In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;88%
7232-21-5

reglan

364-62-5

metoclopramide

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol; dichloromethane65%
4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

100-36-7

N,N-diethylethylenediamine

364-62-5

metoclopramide

Conditions
ConditionsYield
With sodium hydroxide; acetic acid 1.) 90-95 deg C, 4 h, 2.) water, heating; Yield given. Multistep reaction;
150007-96-8

C11H12ClNO5

100-36-7

N,N-diethylethylenediamine

364-62-5

metoclopramide

Conditions
ConditionsYield
In tetrahydrofuran for 3h; Ambient temperature; Yield given;
7206-70-4

4-amino-5-chloro-2-methoxybenzoic acid

364-62-5

metoclopramide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 1 h / 0 °C
2: tetrahydrofuran / 3 h / Ambient temperature
View Scheme
27492-84-8

Methyl 4-amino-2-methoxybenzoate

364-62-5

metoclopramide

Conditions
ConditionsYield
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
4093-29-2

methyl 4-(acetylamino)-o-anisate

364-62-5

metoclopramide

Conditions
ConditionsYield
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
7206-70-4

4-amino-5-chloro-2-methoxybenzoic acid

100-36-7

N,N-diethylethylenediamine

54769-22-1

1-methanesulfonyloxy-1,2,3-benzotriazole

364-62-5

metoclopramide

Conditions
ConditionsYield
With sodium hydroxide; triethylamine In chloroform; water
89881-28-7

C17H27ClN4O2

364-62-5

metoclopramide

Conditions
ConditionsYield
Stage #1: C17H27ClN4O2 With ethylenediamine In ethanol for 10h; Reflux;
Stage #2: With water
2.32 g
201230-82-2

carbon monoxide

1285695-15-9

2-chloro-4-iodo-5-methoxyaniline

100-36-7

N,N-diethylethylenediamine

364-62-5

metoclopramide

Conditions
ConditionsYield
With triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 80℃; Inert atmosphere; Sealed chamber;63.2 mg

Metoclopramide Specification

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.

Metoclopramide can be used to get metoclopramide N-oxide

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.

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