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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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-
- Metoclopramide
- o-Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-
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
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-NSmiles
CCN(CC)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.