Acepromazine

HCID 6077CAS 61-00-7

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

ACEPROMAZINEAcetylpromazineAcetopromazine61-00-7AcepromazinaAtravetAcezine 2Acepromazinum10-(3-Dimethylaminopropyl)phenothiazin-3-yl methyl ketoneConcentrat vo3410-(3-Dimethylaminopropyl)phenothiazine-3-ethyloneEthanone, 1-(10-(3-(dimethylamino)propyl)-10H-phenothiazin-2-yl)-
Show more names
1522CBA 23051NotensilVetranquilAids013600Aids-013600Acetylperazine
54EJ303F0R1-(10-(3-(Dimethylamino)propyl)-10H-phenothiazin-2-yl)ethanoneEthanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-1-[10-(3-DIMETHYLAMINO-PROPYL)-10H-PHENOTHIAZIN-2-YL]-ETHANONEDTXSID1022552CHEBI:449321-{10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethanone1-{10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethan-1-one

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

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Listed in ZINC15

Solubility9.80e-03 g/L
Animal Drugs · 2 items

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Melting Point · 2 items

< 25 °C

< 25 °C

Physical DescriptionSolid
Collision Cross Section · 4 items

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

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

Hazard Classes and CategoriesAcute Tox. 3 (100%)

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 · 2 items

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1 item

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 · 1 item

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).

Biological Half-Life3 hours in horses.
MeSH Pharmacological Classification · 2 items

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.

Cellular LocationsExtracellular

Uses & manufacturing

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan

Applications

UsesSedative (veterinary).

Suppliers14 total

中梦研(湖北)科技有限公司0717-6300888 18062399888 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hangzhou Sage Chemical Co., Ltd.+86057186818502 13588463833 · [email protected]
XI'AN TIANGUANGYUAN BIOTECH CO., LTD.—
玺标(上海)科技有限公司18512111473 18512111473 · [email protected]
Additional notes · 1 item

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

1 records

Linked notes

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