Aceprometazine
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Basic information
- CAS
13461-01-3- Standard SMILES
CC(=O)c1ccc2c(c1)N(CC(C)N(C)C)c1ccccc1S2- InChIKey
XLOQNFNTQIRSOX-UHFFFAOYSA-N- Molecular formula
- C19H22N2OS
- Average molar mass
- 326.5 g/mol
- Monoisotopic mass
- 326.1452845
Overview
Aceprometazine is a phenothiazine compound having an acetyl group at the 2-position and a 2-(dimethylamino)-1-propyl group at the 10-position. It has a role as an anxiolytic drug, a sedative and a histamine antagonist. It is a tertiary amine, a member of phenothiazines, a methyl ketone and an aromatic ketone.
Names & identifiers
- Preferred name
- Aceprometazine
- IUPAC
- 1-[10-[2-(dimethylamino)propyl]phenothiazin-2-yl]ethanone
- English name
- aceprometazine
- Molecular formula
- C19H22N2OS
- Molecular weight
- 326.46
Names & synonyms
AceprometazineAcepromethazine13461-01-3AceprometazinaAceprometazinum10-(2-(Dimethylamino)propyl)phenothiazin-2-yl methyl ketoneCB 1664984N9YTM4YCB-1664CHEBI:537701-(10-(2-(Dimethylamino)propyl)-10H-phenothiazin-2-yl)ethanoneDTXSID00864407
Show more names
1-[10-[2-(Dimethylamino)propyl]-10H-phenothiazin-2-yl]ethanoneEthanone, 1-[10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-
1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethanone1-{10-[2-(DIMETHYLAMINO)PROPYL]-10H-PHENOTHIAZIN-2-YL}ETHAN-1-ONE1-(10-(2-(dimethylamino)propyl)-10H-phenothiazin-2-yl)ethan-1-oneRefChem:108764DTXCID00812928236-661-9Aceprometazinum [INN-Latin]Aceprometazina [INN-Spanish]
Database identifiers
- CAS
13461-01-3- PubChem CID
- 26035
- DTXSID
DTXSID00864407- ChEMBL
CHEMBL2104054
Properties
Computed structural propertiesFilling in
- XLogP
- 4.3
- Topological polar surface area
- 48.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 428
Experimental & physicochemical properties
Solubility1.22e-02 g/L
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 490.1 · 490.1±45.0 °C(Predicted)
- Density
- 1.1075 · 1.1075 (rough estimate)
- refractive index
- 1.595 · 1.5950 (estimate)
- solubility
- Chloroform (Slightly), Methanol (Sparingly)
- pka
- 8.93 · 8.93±0.50(Predicted)
- form
- A liquid
- FDA UNII
- 984 N9YTM4Y · 984N9YTM4Y
- Symbol(GHS)
- 7 · GHS07,GHS09,GHS05
- Signal word
- Danger
- Hazard statements
- 317 · H317-H318-H411-H302
- Precautionary statements
- 261 · P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310
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
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- Toxicity
- LD50 orl-mus: 517 mg/kg AAREAV 21,543,64
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS09,GHS05
- Hazard statements
- H317-H318-H411-H302
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310
Chemistry & industry
Pharmacology
PharmacodynamicsAceprometazine is a drug with neuroleptic and anti-histamine properties. It is not widely prescribed.
Mechanism of ActionAceprometazine, acting as an H1-receptor antagonist can induce sedation by being able to cross the blood-brain-barrier and binding to H1-receptors in the central nervous system.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.
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 ExcretionRapidly absorbed following oral administration.
Cellular LocationsMembrane
Applications
UsesAcepromethazine is a phenothiazine derivative that is often used in combination with Meprobamate (M227750) for the treatment of sleep disorders.
Related reactions
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Compound notes
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