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Substance Name: Metoclopramide [INN:BAN:JAN]
RN: 364-62-5
UNII: L4YEB44I46
InChIKey: TTWJBBZEZQICBI-UHFFFAOYSA-N

Note

  • A dopamine D2 antagonist that is used as an antiemetic.

Molecular Formula

  • C14-H22-Cl-N3-O2

Molecular Weight

  • 299.8
 

Classification Codes

  • Antiemetics
  • Autonomic Agents
  • Central Nervous System Agents
  • Dopamine Agents
  • Dopamine Antagonists
  • Dopamine D2 Receptor Antagonists
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Metoclopramide
  • Metoclopramide [INN:BAN:JAN]

MeSH Heading

  • Metoclopramide

Synonyms

  • 2-Methoxy-4-amino-5-chloro-N,N-dimethylaminoethyl)benzamide
  • 2-Methoxy-5-chloroprocainamide
  • 4-Amino-5-chloro-2-methoxy-N-(beta-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
  • BRN 1884366
  • DEL 1267
  • EINECS 206-662-9
  • Gimoli
  • HSDB 7841
  • Megaldrate
  • Metadrate
  • Methochlopramide
  • Metochlopramide
  • Metoclol
  • Metoclopramida
  • Metoclopramida [INN-Spanish]
  • Metoclopramide
  • Metoclopramidum
  • Metoclopramidum [INN-Latin]
  • Moriperan
  • N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide
  • Plasil
  • Plasil (pharmaceutical)
  • Primperan
  • Reliveran
  • UNII-L4YEB44I46

Systematic Names

  • Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy- (9CI)
  • Metoclopramide
  • o-Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)- (8CI)

Registry Numbers

CAS Registry Number

  • 364-62-5

FDA UNII

  • L4YEB44I46

Related Registry Numbers

  • 2576-84-3 (di-hydrochloride)
  • 54143-57-6 (mono-hydrochloride, mono-hydrate)
  • 7232-21-5 (mono-hydrochloride)

System Generated Number

  • 0000364625

Structure Descriptors

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

c1(cc(C(=O)NCCN(CC)CC)c(cc1N)OC)Cl

Toxicity

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) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE		 Archives of Disease in Childhood. Vol. 55, Pg. 310, 1980.
infant TDLo oral 3mg/kg/9H-I (3mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 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: TOXIC PSYCHOSIS

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 147.25 deg C   EXP
pKa Dissociation Constant 9.27 (none) 25 EXP
log P (octanol-water) 2.62 (none)   EXP
Water Solubility 200 mg/L 25 EXP
Vapor Pressure 4.61E-09 mm Hg 25 EST
Henry's Law Constant 8.74E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.05E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.