Metoclopramide

HCID 4168CAS 364-62-5

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Basic information

Standard SMILES: CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OC
InChIKey: TTWJBBZEZQICBI-UHFFFAOYSA-N
Molecular formula: C14H22ClN3O2
Average molar mass: 299.79 g/mol
Monoisotopic mass: 299.1400546

Names & identifiers

Preferred name: Metoclopramide
IUPAC: 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
English name: 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
Molecular formula: C14H22ClN3O2
Molecular weight: 299.8

Names & synonyms

metoclopramide364-62-5MethochlopramideMetochlopramideReliveranMetaclopramideElietenTerperanMetoclopramida4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamideMetoclopramidum2-Methoxy-5-chloroprocainamide

Show more names

Primperan4-amino-5-chloro-n-(2-(diethylamino)ethyl)-n-anisamidC07868ParmidPlasilMetoclolMetramid

4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide5-Chloro-2-methoxyprocainamideMethoxyclopramide4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamideBenzamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-DTXSID60451694-Amino-5-chloro-2-methoxy-N-(beta-diethylaminoethyl)benzamideN-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide

Database identifiers

CAS: 364-62-5
PubChem CID: 4168
DTXSID: DTXSID6045169
ChEMBL: CHEMBL86
ChEBI: CHEBI:107736
UNII: L4YEB44I46
EC Number: 206-662-9
Nikkaji: J2.037K

Properties

Computed structural properties

XLogP: 2.6
Topological polar surface area: 67.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 7
Heavy atoms: 20
Formal charge: 0
Complexity: 300

Physicochemical properties

Melting point: 146 · 146-148°C
Boiling point: 418.7 · 418.7±45.0 °C(Predicted)
Density: 1.2432 · 1.2432 (rough estimate)
refractive index: 1.52 · 1.5200 (estimate)
storage temp.: 2 · 2-8°C
solubility: Practically insoluble in water, sparingly soluble or slightly soluble in ethanol (96 per cent), slightly soluble in methylene chloride
pka: 0.42 · pKa 0.42± 0.03;9.71± 0.02(H2O)(Approximate)
form: Solid
color: White to Off-White
BRN: 1884366 · 1884366
Major Application: forensics and toxicologypharmaceutical (small molecule)
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)
InChIKey: TTWJBBZEZQICBI-UHFFFAOYSA-N
SMILES: C(NCCN(CC)CC)(=O)C1=CC(Cl)=C(N)C=C1OC
CAS DataBase Reference: 364 · 364-62-5(CAS DataBase Reference)
NCI Dictionary of Cancer Terms: metoclopramide
FDA UNII: 4 YEB44I46 · L4YEB44I46
ATC code: 3 FA01 · A03FA01
NIST Chemistry Reference: 4 · Benzamide, 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxy-(364-62-5)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312-P501
Hazard Codes: Xn
Risk Statements: 22 · 22-64
Safety Statements: 36 · 36/37
WGK Germany: 3 · 3
HS Code: 2924.29 · 2924.29.7790
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral
Hazardous Substances Data: 364 · 364-62-5(Hazardous Substances Data)
REACH Registrations: Active

Safety & regulation

Safety data

wgk: 3
hs_code: 2924.29.7790
risk_code: 22-64
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 36/37
Storage Class: 11 - Combustible Solids
Hazard statements: H302
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P264-P270-P301+P312-P501
Hazardous Substances Data: 364-62-5(Hazardous Substances Data)

Chemistry & industry

Applications · 4 items

UsesMetoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.

Usesantidiabetic

UsesMetoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.

General DescriptionMetoclopramide is typically employed as an antiemetic drug or a gastrointestinal prokinetic drug in adults and children.

Upstream & downstream products

Upstream raw materials

Downstream products

N-Desethyl MetoclopraMide

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

济南诚汇双达生物有限公司053158897070 15550412551

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.