Promazine
Overview
Description
Promazine is a phenothiazine derivative used primarily as a tranquilizer in veterinary medicine and as a short-term treatment for psychomotor agitation in humans . It has weak antipsychotic effects and is not commonly used to treat psychoses . This compound acts similarly to chlorthis compound and causes sedation . It belongs to the typical antipsychotic and phenothiazine class of drugs .
Scientific Research Applications
Promazine has several scientific research applications. It is used in the treatment of psychomotor agitation and as a tranquilizer in veterinary medicine . Additionally, it is used in electrochemical sensors for monitoring pharmaceutical compounds in biological samples . This compound is also studied for its potential use in removing phenothiazines from environmental samples using biochar .
Mechanism of Action
Target of Action
Promazine, a phenothiazine antipsychotic, primarily targets a variety of receptors in the brain . Its primary targets include dopamine receptors (types 1, 2, and 4) , serotonin (5-HT) receptor types 2A and 2C , muscarinic receptors 1 through 5 , alpha(1)-receptors , and histamine H1-receptors . These receptors play crucial roles in transmitting signals between brain cells .
Mode of Action
This compound acts as an antagonist at its target receptors . This means it binds to these receptors and inhibits their activity. In particular, it blocks dopamine receptors, which are involved in transmitting signals between brain cells . When there is an excess amount of dopamine in the brain, it can cause over-stimulation of dopamine receptors . By blocking these receptors, this compound helps to regulate this signal transmission .
Biochemical Pathways
It is known that the drug’s antagonistic action on dopamine and serotonin receptors can affect various neural pathways and alter neurotransmission
Pharmacokinetics
It is known that this compound is a small molecule , which suggests it may be well-absorbed and distributed throughout the body. The metabolism of this compound is likely hepatic, as with other phenothiazines . More research is needed to fully understand the ADME properties of this compound and their impact on its bioavailability.
Result of Action
The molecular and cellular effects of this compound’s action primarily involve the regulation of neurotransmission in the brain. By blocking various receptors, this compound can help to regulate the transmission of signals between brain cells . This can help to manage conditions such as schizophrenia and psychomotor agitation .
Action Environment
The action, efficacy, and stability of this compound can be influenced by various environmental factors. For example, in veterinary medicine, this compound is used as a tranquilizer and its efficacy can be influenced by the animal’s health status and other concurrent medications . .
Safety and Hazards
Biochemical Analysis
Biochemical Properties
Promazine acts by blocking a variety of receptors in the brain, particularly dopamine receptors . Dopamine is involved in transmitting signals between brain cells . When there is an excess amount of dopamine in the brain, it causes over-stimulation of dopamine receptors .
Cellular Effects
This compound has weak extrapyramidal and autonomic side effects which lead to its use in the elderly, for restless or psychotic patients .
Molecular Mechanism
The mechanism of action of this compound involves antagonism at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors .
Temporal Effects in Laboratory Settings
This compound is subject to considerable first-pass metabolism, resulting in significant plasma concentration variations between patients . It is highly toxic in overdose and can result in grand mal seizures, QT prolongation, and comas .
Dosage Effects in Animal Models
In large male animals, protrusion of the penis may occur . Excitement, restlessness, sweating, trembling, and, rarely, seizures and recumbency may occur .
Metabolic Pathways
Three types of metabolic mechanisms were characterized, including S-oxidation, aromatic hydroxylation, and N-dealkylation . The calculated results demonstrate that N14-demethylation is the most thermodynamically and kinetically favorable metabolic pathway of this compound, followed by S5-oxidation .
Preparation Methods
Promazine can be synthesized through various methods. One common method involves reacting diethylamine and epoxypropane to obtain 1-diethylamino-2-propanol, which is then reacted with chloride sulfoxide and toluene to obtain 1-diethylamino-2-chloropropane . This intermediate is then reacted with phenothiazine to obtain crude this compound, which is purified and salified with hydrochloric acid to obtain this compound hydrochloride . Industrial production methods often involve controlling raw material dosage, reaction temperature, and pH value to achieve high yield and purity .
Chemical Reactions Analysis
Promazine undergoes various chemical reactions, including oxidation, reduction, and substitution. For example, it can be oxidized by sodium N-bromo-benzenesulfonamide in acidic medium to form this compound S-oxide . Common reagents used in these reactions include hydrochloric acid, methanol, and activated carbon . The major products formed from these reactions include this compound S-oxide and other oxidized derivatives .
Comparison with Similar Compounds
Promazine is similar to other phenothiazine derivatives such as chlorthis compound and promethazine . it has weaker antipsychotic effects compared to chlorthis compound . This compound and promethazine both bind to GDP-KRAS, but this compound has a higher affinity . Other similar compounds include cariprazine and quetiapine, which are atypical antipsychotics used to treat schizophrenia and bipolar disorder .
Properties
IUPAC Name |
N,N-dimethyl-3-phenothiazin-10-ylpropan-1-amine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
ZGUGWUXLJSTTMA-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CN(C)CCCN1C2=CC=CC=C2SC3=CC=CC=C31 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C17H20N2S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID2023517 |
Source
|
| Record name | Promazine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID2023517 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
284.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Promazine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014564 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Boiling Point |
203-210 °C at 3.00E-01 mm Hg, 203-210 °C @ 0.3 mm Hg |
Source
|
| Record name | Promazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00420 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PROMAZINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3172 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Solubility |
Sol in methanol, ethanol, chloroform /Hydrochloride/, Practically insol in ether, benzene /Hydrochloride/, In water, 14.2 mg/l @ 24 °C, 2.07e-02 g/L |
Source
|
| Record name | Promazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00420 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PROMAZINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3172 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Promazine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014564 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Mechanism of Action |
Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine., THERE IS AN ADENYLATE CYCLASE IN LIMBIC SYSTEM, AS WELL AS IN CAUDATE NUCLEUS, THAT IS SPECIFICALLY ACTIVATED BY DOPAMINE. ...ACTIVATION OF...ENZYME IS... BLOCKED BY...PHENOTHIAZINES. ...THERAPEUTIC EFFICACY & SIDE EFFECTS MAY RELATE TO INHIBITION OF DOPAMINE ACTIVATION OF ADENYLATE CYCLASE. /PHENOTHIAZINES/, ...PHENOTHIAZINES, BLOCK DOPAMINE RECEPTORS & INCR TURNOVER RATE OF DOPAMINE IN CORPUS STRIATUM. INCR TURNOVER RATE IS BELIEVED TO BE RESULT OF NEURONAL FEEDBACK MECHANISM. ...FIRING OF.../IDENTIFIED DOPAMINERGIC NEURONS IN SUBSTANTIA NIGRA & VENTRAL TEGMENTAL AREAS/ IS INCR BY ANTIPSYCHOTIC PHENOTHIAZINES. /PHENOTHIAZINES/ |
Source
|
| Record name | Promazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00420 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3172 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Oily liq | |
CAS No. |
58-40-2 |
Source
|
| Record name | Promazine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=58-40-2 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Promazine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000058402 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Promazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00420 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | promazine | |
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| Record name | Promazine | |
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| Record name | Promazine | |
| Source | European Chemicals Agency (ECHA) | |
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| Record name | PROMAZINE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/O9M39HTM5W | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3172 | |
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| Record name | Promazine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014564 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
< 25 °C |
Source
|
| Record name | Promazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00420 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Promazine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014564 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Q1: What is the primary mechanism of action of Promazine?
A1: While the precise mechanism of action remains an area of ongoing research, this compound is understood to primarily act as a dopamine antagonist. It binds to dopamine receptors, particularly D2 receptors, in the brain, thereby blocking the action of dopamine. [] This dopamine antagonism is thought to contribute to its antipsychotic effects. []
Q2: Does this compound affect other neurotransmitter systems?
A2: Yes, in addition to its effects on dopamine receptors, this compound also interacts with adrenergic receptors, demonstrating a strong antiadrenergic action. [] This interaction contributes to some of its side effects, including potential for faintness and palpitation. []
Q3: What is the molecular formula and weight of this compound?
A3: this compound's molecular formula is C17H20N2S, and its molecular weight is 284.42 g/mol.
Q4: What are the key structural differences between this compound and Chlorthis compound?
A4: this compound and Chlorthis compound share the same basic phenothiazine structure. The key difference lies in the absence of a chlorine atom at the 2-position of the phenothiazine ring in this compound. This subtle structural variation contributes to the differences observed in their pharmacological profiles. [, , ]
Q5: Is there spectroscopic data available for this compound and its metabolites?
A5: Yes, various spectroscopic techniques, including mass spectrometry and UV spectroscopy, have been employed to characterize this compound and its metabolites. For example, mass spectral analysis has been used to identify the dimeric product and 2-chlorophenothiazine sulfoxide formed during the photodecomposition of Chlorthis compound. [] Additionally, UV spectroscopy has been utilized to differentiate between this compound, Chlorthis compound, and their respective sulfoxide metabolites based on their unique absorption spectra. []
Q6: How is this compound metabolized in the body?
A6: this compound undergoes extensive metabolism in the liver, primarily via hydroxylation followed by conjugation with glucuronic acid and, to a lesser extent, with sulfuric acid. [] These metabolic processes lead to the formation of numerous metabolites, with over 30 different metabolites identified in horse urine. []
Q7: Does the presence of liver disease affect this compound pharmacokinetics?
A7: Yes, studies in patients with hepatic cirrhosis have shown significant alterations in this compound pharmacokinetics. [] These alterations include reduced total plasma clearance, reduced free drug clearance, reduced metabolic clearance, and increased elimination half-life. [] These findings highlight the importance of careful dosage adjustments in patients with liver cirrhosis.
Q8: How does the route of administration affect this compound's pharmacokinetic profile?
A8: The route of administration significantly influences the pharmacokinetics of this compound. While intravenous administration results in rapid absorption and distribution, oral and sublingual administration lead to slower absorption and prolonged elimination half-lives. [] Furthermore, the proportion of different metabolites excreted in the urine may vary depending on the route of administration. []
Q9: What in vitro models have been used to study this compound's effects?
A9: this compound's effects have been investigated using various in vitro models, including isolated rat atria. [] In these models, this compound has been shown to influence both contractile force and rate, as well as modulate the response to noradrenaline. [] Such studies provide insights into the direct effects of this compound on cardiac tissue.
Q10: What animal models have been used to study this compound?
A10: this compound's effects have been extensively studied in various animal models, including rats, mice, horses, and pigeons. [, , , ] These models have been instrumental in understanding the drug's behavioral effects, metabolic pathways, and potential toxicity. For example, studies in horses have revealed the extensive metabolism of this compound, while studies in pigeons have provided insights into its effects on operant conditioning paradigms. [, ]
Q11: What are some of the known side effects of this compound?
A11: this compound, like other phenothiazine derivatives, can induce a range of side effects. Some of the commonly reported side effects include drowsiness, dizziness, postural hypotension, and Parkinsonian symptoms. [] In rare instances, more serious adverse effects such as agranulocytosis and seizures have been reported. [, ]
Q12: What analytical techniques are commonly employed to measure this compound levels?
A12: Various analytical methods have been developed for the detection and quantification of this compound in biological samples. Gas chromatography (GC) coupled with nitrogen-phosphorus detection (NPD) is a highly sensitive and selective method that allows for the simultaneous determination of this compound and its metabolites in human blood and plasma. [] High-performance liquid chromatography (HPLC) coupled with tandem mass spectrometry (MS/MS) offers another powerful approach for analyzing this compound and its metabolites in various matrices. []
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
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