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N,N-Dimethyl-10H-phenothiazin-10-propanamin-monohydrochlorid

Promazine Hydrochloride

HCID 5887
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
53-60-1
Standard-SMILES
CN(C)CCCN1c2ccccc2Sc2ccccc21.Cl
InChIKey
JIVSXRLRGOICGA-UHFFFAOYSA-N
Summenformel
C17H21ClN2S
Durchschnittliche Molmasse
320,9 g/mol
Monoisotopische Masse
320,1113975

Überblick

Promazine Hydrochloride is the hydrochloride salt form of promazine, a phenothiazine derivative with antipsychotic and antiemetic properties. Promazine hydrochloride blocks postsynaptic dopamine receptors D1 and D2 in the mesolimbic and medullary chemoreceptor trigger zone (CTZ), thereby decreasing stimulation of the vomiting center in the brain and psychotic effects, such as hallucinations and delusions. In addition, this agent blocks alpha-adrenergic receptors and exhibits strong anticholinergic activity.

Namen und Bezeichner

Bevorzugter Name
Promazine Hydrochloride
IUPAC
N,N-dimethyl-3-phenothiazin-10-ylpropan-1-amine;hydrochloride
Lokaler Name
N,N-Dimethyl-10H-phenothiazin-10-propanamin-monohydrochlorid
Englischer Name
Promazine hydrochloride
Summenformel
C17H21ClN2S
Molmasse
320.88

Namen und Synonyme

PROMAZINE HYDROCHLORIDE53-60-1Promazine HclStarazinTalofenDTXSID4046949NSC-1746810-(gamma-Dimethylamino-n-propyl)phenothiazine hydrochlorideU16EOR79U410H-Phenothiazine-10-propanamine, N,N-dimethyl-, monohydrochloridePromazine hydrochloride (USP)Promazine hydrochloride [USP]
Weitere Namen anzeigen
rp4560LiranolPrazineRP 4560SparineVerofenMegaphenPromwill
10-(3-(Dimethylamino)propyl)phenothiazine monohydrochlorideDTXCID2026949NSC17468CHEBI:846010-[3-(Dimethylamino)propyl]phenothiazine monohydrochlorideTranquazineVerophenePromazine chloride

Datenbank-Bezeichner

CAS
53-60-1
PubChem CID
5887
DTXSID
DTXSID4046949

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
31,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
4
Schwere Atome
21
Formalladung
0
Komplexität
285

Experimentelle und physikochemische Eigenschaften

Solubility>48.1 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsFDA approved animal drugs -> Active ingredient
Collision Cross Section161.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
174 · 174-176C
Dichte
1.1435 · 1.1435 (rough estimate)
Brechungsindex
1.6 · 1.6000 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
Aggregatzustand
Solid
Farbe
White
BRN
3753230 · 3753230

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information10H-Phenothiazine-10-propanamine, N,N-dimethyl-, monohydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 10H-Phenothiazine-10-propanamine, N,N-dimethyl-, monohydrochloride: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxikologische Informationen

TreatmentIn severe cases, consider supportive therapy. Maintain clear airway and adequate hydration. Anti-Parkinson drugs, as well as benztropine mesylate, and barbiturates can be use to relieve extrapyramidal symptoms (A632).
Health Effects · 1 Eintrag

It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon either. Other effects include endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia (A308, L1149).

Exposure Routes

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Hepatic, primarily to N-desmethylpromazine and promazine sulfoxide. Absorption may be erratic and peak plasma concentrations show large interindividual differences. The metabolism occurs through oxidative processes mediated largely by hepatic microsomal and other drug metabolizing enzymes. Antoher step is the conjugaion with glucuronic acid. Other reactions include hydroxylation, demetylation, and sulfoxide formation. Moreover, metabolic alterations in side chain may also occur (A308, A631).

MeSH Pharmacological Classification · 3 Einträge

Drugs used to prevent NAUSEA or VOMITING.

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.

Verwendung und Herstellung

UsesUsed as an adjunct for short term treatment of moderate and severe psychomotor agitation. Also used to treat agitation or restlessness in the elderly.
General Manufacturing Information10H-Phenothiazine-10-propanamine, N,N-dimethyl-, hydrochloride (1:1): INACTIVE

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Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEMBL
CHEMBL1200469
UNII
U16EOR79U4
EC Number
200-179-7
Major Application
clinical testing
InChI
1S/C17H20N2S.ClH/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;1H
InChIKey
JIVSXRLRGOICGA-UHFFFAOYSA-N
SMILES
Cl[H].CN(C)CCCN1c2ccccc2Sc3ccccc13
CAS Datenbank
53 · 53-60-1(CAS DataBase Reference)
NIST chemische Informationen
-10 H-phenothiazine-1-propanamine · N,N-dimethyl-10H-phenothiazine-1-propanamine hydrochloride(53-60-1)
EPA chemische Informationen
Promazine hydrochloride (53-60-1)
Inhalation; dermal or skin contact; ingestion (MSDS, A308). Absorption may be erratic and peak plasma concentrations show large interindividual differences.
Toxicity Summary · 1 Eintrag

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.

Signs and SymptomsSide effects include: extrapyramidal symptoms, drowsiness, weight gain, dry mouth, constipation, endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 140 mg/kg (Intraperitoneal, Mouse)

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
2934302300
RTECS-Nr.
SO8575000
risk_code
22-43
hazard_code
Xn
safety_code
36
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 OralSkin Sens. 1

Anwendungen

VerwendenPromazine hydrochloride has been used in conductivity and surface tension measurements and for testing inhibition of feline coronavirus (FCoV) in Felis catus whole fetus-4 (fcwf-4) cells.

Anbieter80 Anbieter

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Ergänzende Hinweise

DefinitionIsomeric with promethazine hydrochloride.