Basic information
- Standard SMILES
CC(=O)c1ccc2c(c1)N(CCCN(C)C)c1ccccc1S2- InChIKey
NOSIYYJFMPDDSA-UHFFFAOYSA-N- Molecular formula
- C19H22N2OS
- Average molar mass
- 326.5 g/mol
- Monoisotopic mass
- 326.14528432
Overview
Acepromazine is a member of the class of phenothiazines that is 10H-phenothiazine substituted by an acetyl group at position 2 and a 3-(dimethylamino)propyl group at position 10. It has a role as a phenothiazine antipsychotic drug. It is a member of phenothiazines, a tertiary amino compound, a methyl ketone and an aromatic ketone.
Names & identifiers
- Preferred name
- Acepromazine
- IUPAC
- 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]ethanone
- English name
- acepromazine
- Molecular formula
- C19H22N2OS
- Molecular weight
- 326.46
Names & synonyms
Show more names
Database identifiers
- CAS
61-00-7- PubChem CID
- 6077
- DTXSID
DTXSID1022552- ChEMBL
CHEMBL39560- ChEBI
CHEBI:44932- UNII
- 54EJ303F0R
- EC Number
- 200-496-0
- Nikkaji
- J4.812G
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 48.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 414
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
Pharmaceuticals -> Listed in ZINC15
Animal Drugs
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point
< 25 °C
< 25 °C
Collision Cross Section
176.6 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
163.89 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
160.5 Ų [M+H]+ [CCS Type: TW]
176.22 Ų [M+H]+
Physicochemical properties
- Melting point
- 25 °C · <25 °C
- Boiling point
- 0.5 · bp0.5 220-240°
- Density
- 1.1075 · 1.1075 (rough estimate)
- refractive index
- 1.595 · 1.5950 (estimate)
- pka
- 9.41 · 9.41±0.28(Predicted)
- color
- Orange oil
- Water Solubility
- 16 mg/L · 16mg/L(25 ºC)
- FDA UNII
- 54 EJ303F0R · 54EJ303F0R
- ATC code
- 5 AA04 · N05AA04
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 319 · H319-H317-H311-H335-H315-H331-H301
- Precautionary statements
- 264 · P264-P280-P302+P352-P321-P332+P313-P362-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P264-P280-P305+P351+P338-P337+P313P-P280-P302+P352-P312-P322-P361-P363-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
- Toxicity
- 50 intraperitoneal · LD50 intraperitoneal in mouse: 350mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P264+P265, P270, P271, P272, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 27-01-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/6774
Ethanone, 1-10-3-(dimethylamino)propyl-10H-phenothiazin-2-yl-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- Toxicity
- LD50 intraperitoneal in mouse: 350mg/kg
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H319-H317-H311-H335-H315-H331-H301
- REACH Registrations
- Active
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P264-P280-P305+P351+P338-P337+P313P-P280-P302+P352-P312-P322-P361-P363-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Acepromazine is one of the phenothiazine derivative psychotropic drugs. Acepromazine has actions at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Acepromazine has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity.
Mechanism of Action
Acepromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 - different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism - controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects).
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.
Uses & manufacturing
Applications
UsesSedative (veterinary).
Upstream & downstream products
Upstream raw materials
Suppliers14 total
Additional notes
DefinitionChEBI: Acepromazine is a member of the class of phenothiazines that is 10H-phenothiazine substituted by an acetyl group at position 2 and a 3-(dimethylamino)propyl group at position 10. It has a role as a phenothiazine antipsychotic drug. It is a methyl ketone, an aromatic ketone, a tertiary amino compound and a member of phenothiazines.
Related reactions
Linked notes
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