CAS 364-62-5|metoclopramide

Introduction：Basic information about CAS 364-62-5|metoclopramide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. metoclopramide BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles63
8. Synonyms

Common Name	metoclopramide
CAS Number	364-62-5	Molecular Weight	299.80
Density	1.2±0.1 g/cm3	Boiling Point	454.8±55.0 °C at 760 mmHg
Molecular Formula	C₁₄H₂₂ClN₃O₂	Melting Point	146-148°C
MSDS	ChineseUSA	Flash Point	228.9±31.5 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	metoclopramide
Synonym	More Synonyms

metoclopramide BiologicalActivity

Description	Metoclopramide is a dopamine D2 antagonist that is used as an antiemetic.IC50 Value:Target: D2 ReceptorMetoclopramide is a dopamine receptor antagonist which has been used for treatment of a variety of gastrointestinal symptoms over the last thirty years. In various countries, metoclopramide is the antiemetic drug of choice in pregnant women. Findings provide reassurance regarding the safety of metoclopramide for the fetus when the drug is given to women to relieve nausea and vomiting during pregnancy. Evidence also supports its use for gastroparesis (poor stomach emptying) and gastroesophageal reflux disease. It appears to bind to dopamine D2 receptors where it is a receptor antagonist, and is also a mixed 5-HT3 receptor antagonist/ 5-HT4 receptor agonist.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>Dopamine ReceptorSignaling Pathways >>Neuronal Signaling >>Dopamine ReceptorResearch Areas >>Endocrinology
References	[1]. Navari RM, Nagy CK, Gray SE. The use of olanzapine versus metoclopramide for the treatment of breakthrough chemotherapy-induced nausea and vomiting in patients receiving highly emetogenic chemotherapy. Support Care Cancer. 2013 Jan 12. [2]. Gutiérrez-Hermosillo H, Díaz de León-González E, Beltrán Santiago D et al. Metoclopramide as a risk factor for postprandial hyperglycemia in type 2 diabetes. Nutr Hosp. 2012 Jul-Aug;27(4):1267-71. [3]. Ilan Matok, Sc.Pharm., Rafael Gorodischer, et al. The Safety of Metoclopramide Use in the First Trimester of Pregnancy. N Engl J Med 2009; 360:2528-2535. [4]. DN Bateman, C Kahn, K Mashiter, DS Davies. Pharmacokinetic and concentration-effect studies with intravenous metoclopramide. British Journal of Clinical Pharmacology.1978,6(5): 401-407

Description

Metoclopramide is a dopamine D2 antagonist that is used as an antiemetic.IC50 Value:Target: D2 ReceptorMetoclopramide is a dopamine receptor antagonist which has been used for treatment of a variety of gastrointestinal symptoms over the last thirty years. In various countries, metoclopramide is the antiemetic drug of choice in pregnant women. Findings provide reassurance regarding the safety of metoclopramide for the fetus when the drug is given to women to relieve nausea and vomiting during pregnancy. Evidence also supports its use for gastroparesis (poor stomach emptying) and gastroesophageal reflux disease. It appears to bind to dopamine D2 receptors where it is a receptor antagonist, and is also a mixed 5-HT3 receptor antagonist/ 5-HT4 receptor agonist.

Related Catalog

Signaling Pathways >>GPCR/G Protein >>Dopamine ReceptorSignaling Pathways >>Neuronal Signaling >>Dopamine ReceptorResearch Areas >>Endocrinology

References

[1]. Navari RM, Nagy CK, Gray SE. The use of olanzapine versus metoclopramide for the treatment of breakthrough chemotherapy-induced nausea and vomiting in patients receiving highly emetogenic chemotherapy. Support Care Cancer. 2013 Jan 12.

[2]. Gutiérrez-Hermosillo H, Díaz de León-González E, Beltrán Santiago D et al. Metoclopramide as a risk factor for postprandial hyperglycemia in type 2 diabetes. Nutr Hosp. 2012 Jul-Aug;27(4):1267-71.

[3]. Ilan Matok, Sc.Pharm., Rafael Gorodischer, et al. The Safety of Metoclopramide Use in the First Trimester of Pregnancy. N Engl J Med 2009; 360:2528-2535.

[4]. DN Bateman, C Kahn, K Mashiter, DS Davies. Pharmacokinetic and concentration-effect studies with intravenous metoclopramide. British Journal of Clinical Pharmacology.1978,6(5): 401-407

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	454.8±55.0 °C at 760 mmHg
Melting Point	146-148°C
Molecular Formula	C₁₄H₂₂ClN₃O₂
Molecular Weight	299.80
Flash Point	228.9±31.5 °C
PSA	67.59000
LogP	3.10
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.545
InChIKey	TTWJBBZEZQICBI-UHFFFAOYSA-N
SMILES	CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OC

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: BZ3300000

CHEMICAL NAME :: n-Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-

CAS REGISTRY NUMBER :: 364-62-5

LAST UPDATED :: 199801

DATA ITEMS CITED :: 21

MOLECULAR FORMULA :: C14-H22-Cl-N3-O2

MOLECULAR WEIGHT :: 299.84

WISWESSER LINE NOTATION :: 2N2&2MVR DZ CG FO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 632 mg/kg/59D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - toxic psychosis Behavioral - excitement

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 3600 ug/kg/6D-I

TOXIC EFFECTS :: Behavioral - tremor Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 900 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - diplopia Behavioral - muscle contraction or spasticity

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 111 mg/kg/37W-I

TOXIC EFFECTS :: Peripheral Nerve and Sensation - fasciculations

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 2 mg/kg/1D-C

TOXIC EFFECTS :: Behavioral - excitement

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 2400 ug/kg

TOXIC EFFECTS :: Vascular - BP elevation not characterized in autonomic section

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 14 ug/kg

TOXIC EFFECTS :: Vascular - BP elevation not characterized in autonomic section Biochemical - Neurotransmitters or modulators (putative) - catecholamine levels in sympathetic nerves

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 114 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 340 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 270 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 96 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 190 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 33 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 600 mg/kg/30D-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in ovarian weight Related to Chronic Data - changes in uterine weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 34 mg/kg

SEX/DURATION :: male 60 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - impotence

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1155 mg/kg

SEX/DURATION :: female 33 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Human Leukocyte

DOSE/DURATION :: 100 nmol/L

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 12,1613,1991 *** REVIEWS *** TOXICOLOGY REVIEW AJHPA9 American Journal of Hospital Pharmacy. (American Soc. of Hospital Pharmacists, 4630 Montgomery Ave., Bethesda, MD 20814) V.15- 1958- Volume(issue)/page/year: 38,829,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5297 No. of Facilities: 20 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 821 (estimated) No. of Female Employees: 456 (estimated)

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302-H362
Precautionary Statements	P263
Hazard Codes	Xn
Risk Phrases	22-64
Safety Phrases	36/37
RIDADR	NONH for all modes of transport
WGK Germany	3
HS Code	2924299090

Customs

HS Code	2924299090
Summary	2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles63

The progesterone and estrogen modify the uterine prolactin and prolactin receptor expression of hyperprolactinemic mice.

Gynecol. Endocrinol. 31(2) , 148-51, (2015)

The aim of this study was to evaluate the effects of metoclopramide-induced hyperprolactinemia on the prolactin (PRL) and PRL receptor's expression in the uterus of mice. For this purpose, 49 Swiss mi...

Clinical challenge. Esophageal hiatal hernia.

J. Zoo Wildl. Med. 45(4) , 999-1001, (2014)

[Jejunal intussusceptions as a lead point ectopic pancreatic tissue in a 1-year-old male. Case report].

Cir. Cir. 80(6) , 546-9, (2012)

intussusception is the most common cause of acute bowel obstruction in infants and young children. Incidence has been reported as 1.5 to 4 cases per 1,000 live births. Most intussusceptions are ileoce...

Synonyms

Pramin

Imperan

MAXOLON

Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-

Benzamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-

Reglan

Maxeran

EINECS 206-662-9

Plasil

metoclopramide

Benzenecarboximidic acid, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-

Eucil

Primperan

metoclopramidum [INN_la]

4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzenecarboximidic acid

4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide,Methoxychloroprocainamide

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

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