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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: 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: 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) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: TREMOR
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.