Basic information
- CAS
84-96-8- Standard SMILES
CC(CN(C)C)CN1c2ccccc2Sc2ccccc21- InChIKey
ZZHLYYDVIOPZBE-UHFFFAOYSA-N- Molecular formula
- C18H22N2S
- Average molar mass
- 298.4 g/mol
- Monoisotopic mass
- 298.15036988
Overview
Trimeprazine is a member of phenothiazines.
Names & identifiers
- Preferred name
- (+-)-Trimeprazine
- IUPAC
- N,N,2-trimethyl-3-phenothiazin-10-ylpropan-1-amine
- English name
- Trimeprazine
- Molecular formula
- C18H22N2S
- Molecular weight
- 298.45
Names & synonyms
trimeprazineAlimemazine84-96-8Alimezinedl-TrimeprazineRepetinTeralenAlimemazinaBayer 1219(+-)-TrimeprazineAlimemazinum10-(3-(Dimethylamino)-2-methylpropyl)phenothiazine
Show more names
TeraleneALIMENAZINETrimeperazineMethylpromazine
RP 6549BAYER-121910-(2-Methyl-3-dimethylaminopropyl)-phenothiazineN,N,beta-Trimethyl-10H-phenothiazine-10-propanamine76H78MJJ52RP-654910H-Phenothiazine-10-propanamine, N,N,beta-trimethyl-Phenothiazine, 10-(3-(dimethylamino)-2-methylpropyl)-
Database identifiers
- CAS
84-96-8- PubChem CID
- 5574
- DTXSID
DTXSID9023708- ChEMBL
CHEMBL829- ChEBI
CHEBI:9725- UNII
- 76H78MJJ52
- EC Number
- 201-577-3
- Nikkaji
- J4.905K
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 31.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 311
Experimental & physicochemical properties
LogP
4.6
4.71
Color/FormCRYSTALS
Solubility
CRYSTALS; SOL IN WATER; SLIGHTLY SOL IN ALCOHOL /TARTRATE/
WHITE TO OFF-WHITE CRYSTALLINE POWDER; FREELY SOL IN CHLOROFORM; VERY SLIGHTLY SOL IN ETHER & BENZENE /TARTRATE/
8.35e-03 g/L
Human DrugsPharmaceuticals
Boiling Point
150-175 °C at 3.00E-01 mm Hg
150-175 °C @ 0.3 MM HG
Melting Point
68 °C
68 °C
Physical DescriptionSolid
Stability/Shelf LifeDARKENS ON EXPOSURE TO LIGHT /TARTRATE/
Dissociation Constants
9.11
8.5
9.05
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
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: Alimemazine (EC: 201-577-3)
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Interactions
...MARKEDLY ENHANCES RESPIRATORY DEPRESSION PRODUCED BY MEPERIDINE. ENHANCEMENT OF EFFECTS OF VARIETY OF DRUGS, PARTICULARLY CNS DEPRESSANTS, IS NOT DUE TO INHIBITION OF HEPATIC MICROSOMAL ENZYMES. IN FACT, PHENOTHIAZINES PROMOTE INDUCTION OF THESE ENZYMES. /PHENOTHIAZINES/
MAY INCR TOXICITY OF ORGANOPHOSPHORUS OR OTHER ACETYLCHOLINESTERASE INHIBITORS & PROCAINE. DO NOT USE EPINEPHRINE TO COMBAT ITS HYPOTENSIVE OR DEPRESSANT EFFECTS AS IT POTENTIATES THEM.
POSSIBILITY OF SEVERE HYPOTHERMIA...IN PATIENTS RECEIVING /CONCOMITANT/ ANTIPYRETIC THERAPY...ADDITIVE WITH, OR MAY POTENTIATE, ACTION OF CNS DEPRESSANTS...ATROPINE, HYPOTENSIVE AGENTS, NARCOTICS, BARBITURATES...OTHER SEDATIVES, ANESTHETICS, TRANQUILIZERS...ALCOHOL. /TARTRATE/
Human Toxicity Excerpts
LEUKOCYTOSIS, LEUKOPENIA, & EOSINOPHILIA OCCUR WITH PHENOTHIAZINE MEDICATION. ...HYPERSENSITIVITY REACTION THAT MAY BE URTICARIAL, MACULOPAPULAR, PETECHIAL, OR EDEMATOUS... /PHENOTHIAZINES/
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
Pharmacodynamics
Trimeprazine (also known as Alimemazine) is a tricyclic antihistamine, similar in structure to the phenothiazine antipsychotics, but differing in the ring-substitution and chain characteristics. Trimeprazine is in the same class of drugs as chlorpromazine (Thorazine) and trifluoperazine (Stelazine); however, unlike the other drugs in this class, trimeprazine is not used clinically as an anti-psychotic. It acts as an anti-histamine, a sedative, and an anti-emetic (anti-nausea). Trimeprazine is used principally as an anti-emetic, to prevent motion sickness or as an anti-histamine in combination with other medications in cough and cold preparations. Tricyclic antihistamines are also structurally-related to the tricyclic antidepressants, explaining the antihistaminergic adverse effects of these two drug classes and also the poor tolerability profile of tricyclic H<sub>1</sub>-antihistamines.
Mechanism of ActionTrimeprazine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.
Metabolism/Metabolites
Hepatic
YIELDS 10-(3-DIMETHYLAMINO-2-METHYLPROPYL)PHENOTHIAZINE SULFOXIDE AND 10-(3-METHYLAMINO-2-METHYLPROPYL)PHENOTHIAZINE IN RAT; HEWICK, DS, & BECKETT, AH, BIOCHEM J, 122, 56P (1971). /FROM TABLE/
METABOLIZED PRIMARILY BY THE LIVER. HEPATIC METABOLIC REACTIONS INCLUDE OXIDATION, HYDROXYLATION, DEMETHYLATION, SULFOXIDE FORMATION AND CONJUGATION WITH GLUCURONIC ACID, METABOLIC ALTERATIONS IN THE SIDE CHAIN MAY ALSO OCCUR /HUMAN, ORAL/. /TARTRATE/
MeSH Pharmacological ClassificationAgents, usually topical, that relieve itching (pruritus).
Absorption, Distribution and Excretion
Well absorbed in the digestive tract.
ULTIMATE SOJOURN OF PHENOTHIAZINE DRUGS IN BODY IS EXCEEDINGLY LONG. SIX MO AFTER DISCONTINUATION OF THESE DRUGS, VARIOUS METABOLITES ARE DETECTABLE IN URINE. /PHENOTHIAZINES/
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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