Basic information
- CAS
60-99-1- Standard SMILES
COc1ccc2c(c1)N(C[C@H](C)CN(C)C)c1ccccc1S2- InChIKey
VRQVVMDWGGWHTJ-CQSZACIVSA-N- Molecular formula
- C19H24N2OS
- Average molar mass
- 328.5 g/mol
- Monoisotopic mass
- 328.16093457
Overview
Methotrimeprazine is a member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively. It has a role as an anticoronaviral agent, a non-narcotic analgesic, a phenothiazine antipsychotic drug, a serotonergic antagonist, a dopaminergic antagonist, a cholinergic antagonist and an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor. It is a tertiary amine and a member of phenothiazines. It derives from a hydride of a 10H-phenothiazine.
Names & identifiers
- Preferred name
- Levomepromazine
- IUPAC
- (2R)-3-(2-methoxyphenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
- English name
- (-)-10-(3-[Dimethylamino]-2-methylpropyl)-2-methoxy-phenothiazine maleate salt
- Molecular formula
- C19H24N2OS
- Molecular weight
- 328.47
Names & synonyms
LevomepromazineMETHOTRIMEPRAZINE60-99-1LevopromeLevopromazineNeozineLevomepromazinaNirvanLevomepromazinum2-MethoxytrimeprazineNosinanSK&F 5116
Show more names
LevotominLevomepromazinXP 03rp7044C07192skf5116
RP-7044CL 36467CL 39743XP03RP 7044Bayer 1213Arc-VI-C-59G0LAW7ATQ
Database identifiers
- CAS
60-99-1- PubChem CID
- 72287
- DTXSID
DTXSID1023289- ChEMBL
CHEMBL1764- ChEBI
CHEBI:6838- UNII
- 9G0LAW7ATQ
- EC Number
- 200-495-5
- Nikkaji
- J76.892H
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 41 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 378
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antipsychotics
LogP4.68
Solubility5.25e-03 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Physical DescriptionSolid
Dissociation Constants
9.19
9.19
Collision Cross Section176.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Physicochemical properties
- Melting point
- 117 °C · 117°C
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
Warning
H302 (100%): 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 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationMethotrimeprazine: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Exposure RoutesOral; parental (intramuscular). Methotrimeprazine has an incomplete oral bioavailability, because it undergoes considerable first-pass-metabolism in the liver. Oral bioavailability is approximately 50 to 60%.
Toxicity Summary
Methotrimeprazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, its binding to 5HT2 receptors may also play a role. Methotrimeprazine exerts its actions through a central adrenergic-blocking, a dopamine-blocking, a serotonin-blocking, and a anticholinergic blocking.
Signs and SymptomsSymptoms of overdose include convulsions, spastic movements, and coma.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
ATC Code
N05AA02
N - Nervous system
QN - Nervous system
Pharmacodynamics
Methotrimeprazine is a phenothiazine with pharmacological activity similar to that of both chlorpromazine and promethazine. It has the histamine-antagonist properties of the antihistamines together with central nervous system effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604)
Mechanism of ActionMethotrimeprazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, its binding to 5HT2 receptors may also play a role.
Biological Half-LifeApproximately 20 hours.
Metabolism/Metabolites
Hepatic. Methotrimeprazine is metabolized in the liver and degraded to a sulfoxid-, a glucuronid- and a demethyl-moiety.
Hepatic. Methotrimeprazine is metabolized in the liver and degraded to a sulfoxid-, a glucuronid- and a demethyl-moiety. Half Life: Approximately 20 hours.
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.
Related reactions
0 records
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Compound notes
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