Methotrimeprazine maleate
Basic information
- CAS
7104-38-3- Standard SMILES
COc1ccc2c(c1)N(C[C@H](C)CN(C)C)c1ccccc1S2.O=C(O)/C=C\C(=O)O- InChIKey
IFLZPECPTYCEBR-VIEYUMQNSA-N- Molecular formula
- C23H28N2O5S
- Average molar mass
- 444.5 g/mol
- Monoisotopic mass
- 444.17189317
Overview
Methotrimeprazine is only found in individuals that have used or taken this drug. It 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). 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.
Names & identifiers
- Preferred name
- Methotrimeprazine maleate
- IUPAC
- (Z)-but-2-enedioic acid;(2R)-3-(2-methoxyphenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
- English name
- Levomepromazine maleate
- Molecular formula
- C19H24N2OS.C4H4O4
- Molecular weight
- 444.55
Names & synonyms
levomepromazine maleate7104-38-3Methotrimeprazine maleateMinozinanNeuractilNeurocilMilezinSofminMethoprazineHirnaminLevomepromazine Hydrogen MaleateDTXSID4045399
Show more names
NeruocilLevohalteNeurocil (tablet)Levomepromazine meleateRP 7044 hydrogen maleateLevomepromazine·maleic acidLevomepromazine maleate CRS
Veractil5KN5Y9V01KDTXCID202539910H-Phenothiazine-10-propanamine, 2-methoxy-N,N,beta-trimethyl-, (betaR)-, (2Z)-2-butenedioate (1:1)LevinanRefChem:799026(2R)-3-(2-Methoxy-10H-phenothiazin-10-yl)-N,N,2-trimethylpropylamine monomaleate230-412-8
Database identifiers
- CAS
7104-38-3- PubChem CID
- 5282484
- DTXSID
DTXSID4045399- ChEMBL
CHEMBL1725730- UNII
- 5KN5Y9V01K
- EC Number
Properties
Computed structural properties
- Topological polar surface area
- 116 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 497
Physicochemical properties
- Melting point
- 176 · 176-179°C
- alpha
- 20 · D20 -17° (c = 5 in chloroform)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly), DMF (Slightly), Methanol (Slightly)
- form
- solid
- color
- Off-White to Pale Beige
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- IFLZPECPTYCEBR-VIEYUMQNSA-N
- SMILES
- S1c2c(cc(cc2)OC)N(c3c1cccc3)C[C@@H](CN(C)C)C.OC(=O)\C=C/C(=O)O
- FDA UNII
- 5 KN5Y9V01K · 5KN5Y9V01K
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 317 · H317-H302-H410
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P273-P391-P501
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, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 34 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationMethotrimeprazine maleate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 10H-Phenothiazine-10-propanamine, 2-methoxy-N,N,.beta.-trimethyl-, (Z)-2-butenedioate (1:1), (-)-: Human health tier I assessment
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.
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHepatic. Methotrimeprazine is metabolized in the liver and degraded to a sulfoxid-, a glucuronid- and a demethyl-moiety.
Half Life: Approximately 20 hours.
Uses & manufacturing
Uses
For the treatment of psychosis, particular those of schizophrenia, and manic phases of bipolar disorder. As a potentiator of anesthetics: In general anesthesia where it can be used as both a pre- and post-operative sedative and analgesic. (L1857) As an anti-emetic: For the treatment of nausea and vomiting of central origin.(L1857) As a sedative: For the management of insomnia. (L1857)
Applications
UsesAntipsychotic
UsesThe (R) optical isomer of Methotrimeprazine (M260785), an analgesic/neuroleptic.
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Compound notes
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