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57808-66-9

Basic Information
CAS No.: 57808-66-9
Name: Domperidone
Article Data: 3
Molecular Structure:
Molecular Structure of 57808-66-9 (Domperidone)
Formula: C22 H24 Cl N5 O2
Molecular Weight: 425.918
Synonyms: 5-Chloro-1-(1-(3-(2-oxo-1-benzimidazolinyl)propyl)-4-piperidyl)-2-benzimidazolinone;Domperidonum;Motilium;
EINECS: 260-968-7
Density: 1.341 g/cm3
Melting Point: 242.5oC
Solubility: DMSO: >10 mg/mL
Appearance: white powder
Hazard Symbols: HarmfulXn
Risk Codes: 62-63
Safety: 26-36
PSA: 78.82000
LogP: 3.29110
Synthetic route
64928-87-6

1-(3-aminopropyl)benzimidazol-2-one

53786-28-0

5-chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

57808-66-9

domperidone

Conditions
ConditionsYield
With sodium bromide; sodium sulfite In nitromethane for 32h; Solvent; Concentration; Reflux;51%
67-66-3

chloroform

108-10-1

4-methyl-2-pentanone

62780-89-6

1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one

53786-28-0

5-chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

57808-66-9

domperidone

Conditions
ConditionsYield
With potassium iodide; sodium carbonate In water1.3 parts (30%)
57808-66-9

domperidone

C22H25N5O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide for 35h; Irradiation;50%
57808-66-9

domperidone

domperidone hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 1h;
88-89-1

2,4,6-Trinitrophenol

57808-66-9

domperidone

C6H3N3O7*C22H24ClN5O2

Conditions
ConditionsYield
In methanol for 0.75h;
51-28-5

2,4-Dinitrophenol

57808-66-9

domperidone

C6H4N2O5*C22H24ClN5O2

Conditions
ConditionsYield
In methanol for 0.75h;
1518-16-7

7,7',8,8'-tetracyanoquinodimethane

57808-66-9

domperidone

C12H4N4*C22H24ClN5O2

Conditions
ConditionsYield
In methanol for 0.75h;
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

57808-66-9

domperidone

C8Cl2N2O2*C22H24ClN5O2

Conditions
ConditionsYield
In methanol for 0.75h;

2,6-dibromoquinone-4-chloroimide

57808-66-9

domperidone

C6H2Br2ClNO*C22H24ClN5O2

Conditions
ConditionsYield
In methanol for 0.75h;
101-38-2

2,6-dichloroquinone-4-chloroimide

57808-66-9

domperidone

C6H2Cl3NO*C22H24ClN5O2

Conditions
ConditionsYield
In methanol for 0.75h;
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Chemistry


IUPAC Name: 6-Chloro-3-[1-[3-(2-oxo-3H-benzimidazol-1-yl)propyl]piperidin-4-yl]-1H-benzimidazol-2-one
Molecular Formula: C22H24ClN5O2
Molecular Weight: 425.96
EINECS: 260-968-7
Classification Code: Anti-emetic; Antiemetics; Autonomic Agents; Central Nervous System Agents; Dopamine Agents; Dopamine antagonists; Drug / Therapeutic Agent; Gastrointestinal Agents; Human Data; Neurotransmitter Agents; Peripheral Nervous System Agents; Reproductive Effect
Product Categories: Dopamine receptor
Stability: Stable. Incompatible with strong oxidizing agents.
XLogP3: 3.9
H-Bond Donor: 2
H-Bond Acceptor: 3
Rotatable Bond Count: 5
Tautomer Count: 4
Exact Mass: 425.161853
MonoIsotopic Mass: 425.161853
Topological Polar Surface Area: 67.9
Heavy Atom Count: 30
Complexity: 655
Index of Refraction: 1.637 
Molar Refractivity: 114.03 cm3 
Molar Volume: 317.4 cm
Polarizability: 45.2×10-24 cm3 
Surface Tension: 55.6 dyne/cm 
Density: 1.341 g/cm3
Melting Point: 242.5 °C
Solubility: DMSO: >10 mg/mL
Henry's Law Constant: 6.11E-22 atm-m3/mole at 25 °C
Atmospheric OH Rate Constant: 1.57E-10 cm3/molecule-sec at 25 °C 
Vapour Pressure of Domperidone (CAS NO.57808-66-9): 1.15E-14 mm Hg at 25 °C

Uses

 Domperidone (CAS NO.57808-66-9) is used as a specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 42700ug/kg (42.7mg/kg) BEHAVIORAL: ATAXIA
BEHAVIORAL: ANTIPSYCHOTIC
GASTROINTESTINAL: NAUSEA OR VOMITING
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 244, Pg. 130, 1980.
dog LD50 oral > 160mg/kg (160mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 244, Pg. 130, 1980.
dog LD50 rectal > 120mg/kg (120mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 625, 1984.
dog LD50 subcutaneous > 160mg/kg (160mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 244, Pg. 130, 1980.
guinea pig LD50 intravenous 42900ug/kg (42.9mg/kg) BEHAVIORAL: ATAXIA
GASTROINTESTINAL: NAUSEA OR VOMITING
BEHAVIORAL: ANTIPSYCHOTIC
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 244, Pg. 130, 1980.
human LDLo intravenous 429ug/kg (0.429mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD British Medical Journal. Vol. 288, Pg. 1728, 1984.
human TDLo intravenous 714ug/kg (0.714mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD British Medical Journal. Vol. 288, Pg. 1728, 1984.
infant TDLo oral 1170ug/kg/1D- (1.17mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE Journal of Pediatrics. Vol. 108, Pg. 630, 1986.
man TDLo intramuscular 200ug/kg (0.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Lancet. Vol. 2, Pg. 1259, 1980.
man TDLo oral 234mg/kg/39W- (234mg/kg) ENDOCRINE: GYNECOMASTIA Postgraduate Medical Journal. Vol. 67, Pg. 401, 1991.
mouse LD50 intraperitoneal > 8gm/kg (8000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
mouse LD50 intravenous 46500ug/kg (46.5mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
mouse LD50 oral > 8gm/kg (8000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 1128, 1982.
mouse LD50 subcutaneous > 8gm/kg (8000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
rat LD50 intraperitoneal 61200ug/kg (61.2mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 1128, 1982.
rat LD50 intravenous 41700ug/kg (41.7mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
rat LD50 oral 5243mg/kg (5243mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
BEHAVIORAL: ATAXIA
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
rat LD50 rectal > 250mg/kg (250mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 625, 1984.
rat LD50 subcutaneous > 8gm/kg (8000mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
women TDLo intravenous 600ug/kg/1D (0.6mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Lancet. Vol. 2, Pg. 385, 1985.
women TDLo intravenous 1mg/kg (1mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) British Medical Journal. Vol. 289, Pg. 1579, 1984.
women TDLo rectal 7200ug/kg/30H (7.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE Journal of Pediatrics. Vol. 105, Pg. 852, 1984.
 

Safety Profile

Poison by intravenous and intraperitoneal routes. Human systemic effects by intravenous and intramuscular routes: eye effects, convulsions, muscle spasms and cardiac arrhythmias. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of Cl and NOx.
Hazard Codes: HarmfulXn
Risk Statements: 62-63 
R62: Risk of impaired fertility. 
R63: Possible risk of harm to the unborn child.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany of Domperidone (CAS NO.57808-66-9): 3 

Specification

  Domperidone (CAS NO.57808-66-9), its Synonyms are 2H-Benzimidazol-2-one, 1,3-dihydro-5-chloro-1-(1-(3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl)-4-piperidinyl)- ; 2H-Benzimidazol-2-one, 5-chloro-1-(1-(3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl)-4-piperidinyl)-1,3-dihydro- ; 5-Chloro-1-(1-(3-(2-oxo-1-benzimidazolinyl)propyl)-4-piperidyl)-2-benzimidazolinone ; Domperidonum ; Motilium . It is white powder.