Basic information
- CAS
4093-35-0- Standard SMILES
CCN(CC)CCNC(=O)c1cc(Br)c(N)cc1OC- InChIKey
GIYAQDDTCWHPPL-UHFFFAOYSA-N- Molecular formula
- C14H22BrN3O2
- Average molar mass
- 344.25 g/mol
- Monoisotopic mass
- 343.08954
Overview
4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide is a member of benzamides.
Names & identifiers
- Preferred name
- Bromopride
- IUPAC
- 4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
- English name
- Bromopride
- Molecular formula
- C14H22BrN3O2
- Molecular weight
- 344.25
Names & synonyms
bromopride4093-35-0Bromoprida4-amino-5-bromo-N-(2-(diethylamino)ethyl)-2-methoxybenzamideBromopridum4-Amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamideBromopridMovipride4-Amino-5-bromo-N-(2-(diethylamino)ethyl)-o-anisamideDTXSID0045383NSC-75839175473V2YZK
Show more names
EmorilViadilPraidenPlesiumOpridanEmeprideval13081
N-(Diethylaminoethyl)-2-methoxy-4-amino-5-bromobenzamideDTXCID8025383RefChem:121629A03FA04223-842-2ArtomeyValoprideVAL 13081
Database identifiers
- CAS
4093-35-0- PubChem CID
- 2446
- DTXSID
DTXSID0045383- ChEMBL
CHEMBL399510- ChEBI
CHEBI:95304- UNII
- 75473V2YZK
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 67.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 300
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.62
Melting Point134-135
Collision Cross Section
173.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
135.07 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 148 · 148-150C
- Boiling point
- 435.8 · 435.8±45.0 °C(Predicted)
- Density
- 1.4132 · 1.4132 (rough estimate)
- refractive index
- 1.62 · 1.6200 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 13.84 · 13.84±0.46(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.4% (1 of 41) of reports.
Warning
H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.6%)
Safety data
- wgk
- 3
- rtecs
- BZ3280000
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Hazard statements
- H302-H312-H332
- Precautionary statements
- P280
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Protein Binding40%.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
Drugs used to prevent NAUSEA or VOMITING.
Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.
Absorption, Distribution and ExcretionRenal, 10-14% as original compound.
Applications
DescriptionBromopride is a dopamine D2 receptor antagonist (Ki = 14 nM). It binds to bovine anterior pituitary membranes with an IC50 value of 2.13 μM. Bromopride inhibits cholinesterase activity in vitro in rat plasma and striatum homogenate (IC50s = 67.8 and 38.4 μM, respectively). It increases serum prolactin levels in rats by 100% when used at a dose of 0.02 mol/kg. Bromopride (2.5 mg/kg) decreases locomotion and rearing in an open field test and impairs acquistion, but not retention, of a conditioned avoidance response in a two-way active conditioned avoidance test in rats.
UsesAn antiemetic.Bromopride is used in method and a system for analyzing neuropharmacology of a drug.
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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