Metoclopramide supplier | CasNO.364-62-5

Name
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
EINECS 206-662-9
CAS No. 364-62-5
Article Data53
CAS DataBase
Density 1.162 g/cm³
Solubility
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
Appearance
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;
PSA 67.59000
LogP 2.97450

Synthetic route

: 7206-70-4
4-amino-5-chloro-2-methoxybenzoic acid

: 100-36-7
N,N-diethylethylenediamine

: 364-62-5
metoclopramide

Conditions

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

: 7232-21-5
reglan

: 364-62-5
metoclopramide

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; dichloromethane	65%

: 4093-31-6
methyl 2-methoxy 4-acetamido 5-chloro benzoate

: 100-36-7
N,N-diethylethylenediamine

: 364-62-5
metoclopramide

Conditions

Conditions	Yield
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

Conditions	Yield
In tetrahydrofuran for 3h; Ambient temperature; Yield given;

: 7206-70-4
4-amino-5-chloro-2-methoxybenzoic acid

: 364-62-5
metoclopramide

Conditions

Conditions	Yield
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

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

: 4093-29-2
methyl 4-(acetylamino)-o-anisate

: 364-62-5
metoclopramide

Conditions

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

: 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

Conditions	Yield
With sodium hydroxide; triethylamine In chloroform; water

...Expand

: 89881-28-7
C17H27ClN4O2

: 364-62-5
metoclopramide

Conditions

Conditions	Yield
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

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

...Expand

: 2401-24-3
2-chloro-5-methoxyaniline

: 364-62-5
metoclopramide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate 2: triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 80 °C / Inert atmosphere; Sealed chamber View Scheme

: 364-62-5
metoclopramide

: 38339-95-6
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide

Conditions

Conditions	Yield
With sodium hydride; ethanethiol In N,N-dimethyl-formamide at 100 - 105℃; for 1.5h;	98%

: NH4(1+)*Cr(3+)*4NSC(1-)*2NH2C6H5 = NH4[Cr(NCS)4(NH2C6H5)2]

: 364-62-5
metoclopramide

: 4CNS(1-)*Cr(3+)*2C6H7N*C14H22ClN3O2*H(1+)

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water	97%

: 364-62-5
metoclopramide

: Reinecke's salt

: 4CNS(1-)*2H3N*Cr(3+)*C14H22ClN3O2*H(1+)

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water	96%

: NH4(1+)*Cr(3+)*4NSC(1-)*2NH2CH2C6H5 = NH4[Cr(NCS)4(NH2CH2C6H5)2]

: 364-62-5
metoclopramide

: 4CNS(1-)*Cr(3+)*2C7H9N*H(1+)*C14H22ClN3O2

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water	95%

: 364-62-5
metoclopramide

: 2C6H12N4*4CNS(1-)*Cr(3+)*H4N(1+)

: 2C6H12N4*4CNS(1-)*Cr(3+)*H(1+)*C14H22ClN3O2

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water	93%

: 364-62-5
metoclopramide

: 4CNS(1-)*Cr(3+)*H4N(1+)*2C6H5N3

: 4CNS(1-)*Cr(3+)*H(1+)*2C6H5N3*C14H22ClN3O2

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water	92%

: 364-62-5
metoclopramide

: 4CNS(1-)*Cr(3+)*H4N(1+)*2C3H4N2

: 4CNS(1-)*Cr(3+)*2C3H4N2*C14H22ClN3O2*H(1+)

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water	91%

: 364-62-5
metoclopramide

: 407-25-0
trifluoroacetic anhydride

: 820965-31-9
5-Chloro-N-(2-diethylamino-ethyl)-2-methoxy-4-(2,2,2-trifluoro-acetylamino)-benzamide

Conditions

Conditions	Yield
With triethylamine In chloroform	86%

: 364-62-5
metoclopramide

: 118-75-2
chloranil

: 1569295-24-4
C14H22ClN3O2*C6Cl4O2

Conditions

Conditions	Yield
In methanol at 20℃; for 0.25h; Thermodynamic data;	82%

: 364-62-5
metoclopramide

: 4122-68-3
4-chlorophenyloxyacetyl chloride

: 65569-29-1
cloxacepride

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	80.7%

: 364-62-5
metoclopramide

: 427-49-6
2-cyclopentyl-2-hydroxy-2-phenylacetic acid

: 2-chloro-4-{[2-(diethylamino)ethyl]carbamoyl}-5-methoxyanilinium-2-cyclopentyl-2-hydroxy-2-phenylacetate

Conditions

Conditions	Yield
In acetone for 6h; Inert atmosphere; Reflux;	80%

: 364-62-5
metoclopramide

: 405-78-7
2-(4-fluorophenoxy)acetyl chloride

: 85630-52-0
5-Chloro-N-(2-diethylamino-ethyl)-4-[2-(4-fluoro-phenoxy)-acetylamino]-2-methoxy-benzamide

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	78.3%

: 364-62-5
metoclopramide

: 171367-22-9
metoclopramide N-oxide

Conditions

Conditions	Yield
With dihydrogen peroxide Ambient temperature;	77%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.333333h; Ambient temperature;
Multi-step reaction with 3 steps 1: 86 percent / Et3N / CHCl3 2: 100 percent / m-chloroperbenzoic acid / CHCl3 / Ambient temperature 3: 100 percent / aq. Na2CO3 / methanol / Ambient temperature View Scheme

: 364-62-5
metoclopramide

: 57-13-6
urea

: 65016-46-8
4-Amino-5-cyano-N-(2-diethylamino-ethyl)-2-methoxy-benzamide

Conditions

Conditions	Yield
With nickel(II) acetylacetonate; potassium fluoride; phenylsilane; zinc; bis(2-diphenylphosphinoethyl)phenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 20h;	76%

: 364-62-5
metoclopramide

: 1518-16-7
7,7',8,8'-tetracyanoquinodimethane

: 1569257-76-6
C14H22ClN3O2*C12H4N4

Conditions

Conditions	Yield
In methanol at 20℃; for 0.25h; Thermodynamic data;	75%

: 364-62-5
metoclopramide

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1569257-75-5
C14H22ClN3O2*C8Cl2N2O2

Conditions

Conditions	Yield
In methanol at 20℃; for 0.25h; Thermodynamic data;	73%

: 364-62-5
metoclopramide

: 20143-41-3
(2-chloro-phenoxy)-acetyl chloride

: 65569-40-6
5-Chloro-4-[2-(2-chloro-phenoxy)-acetylamino]-N-(2-diethylamino-ethyl)-2-methoxy-benzamide

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	72.4%

: 364-62-5
metoclopramide

: 62-23-7
4-nitro-benzoic acid

: 1569257-78-8
C14H22ClN3O2*C7H5NO4

Conditions

Conditions	Yield
In methanol at 20℃; for 0.25h; Thermodynamic data;	71%

: 364-62-5
metoclopramide

: C14H21(2)HClN3O2

Conditions

Conditions	Yield
With rhodium(III) chloride; water-d2 In N,N-dimethyl-formamide at 108℃;	70%

: 364-62-5
metoclopramide

: 774-74-3
2-(2,4-dichlorophenoxy)acetyl chloride

: 85630-56-4
5-Chloro-4-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-(2-diethylamino-ethyl)-2-methoxy-benzamide

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	69.6%

: 364-62-5
metoclopramide

: 4878-20-0
2-(4-Chlorophenoxy)propionic acid chloride

: 65569-34-8
5-Chloro-4-[2-(4-chloro-phenoxy)-propionylamino]-N-(2-diethylamino-ethyl)-2-methoxy-benzamide

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	68.3%

: 364-62-5
metoclopramide

: 88-89-1
2,4,6-Trinitrophenol

: 1569257-74-4
C14H22ClN3O2*C6H3N3O7

Conditions

Conditions	Yield
In methanol at 20℃; for 0.25h; Thermodynamic data;	66%

: 364-62-5
metoclopramide

: 34074-28-7
1,2-bis(4-formylphenoxy)ethane

: C44H54Cl2N6O6

Conditions

Conditions	Yield
With acetic acid In ethanol Reflux;	65%

: 99-65-0
meta-dinitrobenzene

: 364-62-5
metoclopramide

: 1569257-77-7
C14H22ClN3O2*C6H4N2O4

Conditions

Conditions	Yield
In methanol at 20℃; for 0.25h; Thermodynamic data;	62%

: 364-62-5
metoclopramide

: 42082-29-1
p-methoxyphenoxyacetyl chloride

: 85630-60-0
5-Chloro-N-(2-diethylamino-ethyl)-2-methoxy-4-[2-(4-methoxy-phenoxy)-acetylamino]-benzamide

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	60%

: 364-62-5
metoclopramide

: 85630-84-8
(2,3-dichlorophenoxy)acetyl chloride

: 85630-58-6
5-Chloro-4-[2-(2,3-dichloro-phenoxy)-acetylamino]-N-(2-diethylamino-ethyl)-2-methoxy-benzamide

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	59.7%

: 364-62-5
metoclopramide

: 20143-44-6
2-(4-iodophenoxy)acetyl chloride

: 65569-50-8
5-Chloro-N-(2-diethylamino-ethyl)-4-[2-(4-iodo-phenoxy)-acetylamino]-2-methoxy-benzamide

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	59.2%

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.

Product Name

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide

Synthetic route

Metoclopramide Specification

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