Basic information
- CAS
362-29-8- Standard SMILES
CCC(=O)c1ccc2c(c1)N(CC(C)N(C)C)c1ccccc1S2- InChIKey
UVOIBTBFPOZKGP-UHFFFAOYSA-N- Molecular formula
- C20H24N2OS
- Average molar mass
- 340.5 g/mol
- Monoisotopic mass
- 340.16093457
Overview
Propiomazine is a member of the class of phenothiazines that is 10H-phenothiazine substituted by a 2-(dimethylamino)propyl group at nitrogen atom and a propanoyl group at position 2. It has a role as a sedative, a phenothiazine antipsychotic drug, a histamine antagonist, a serotonergic antagonist, a dopaminergic antagonist and a muscarinic antagonist. It is a member of phenothiazines, a tertiary amino compound and an aromatic ketone. It derives from a hydride of a 10H-phenothiazine.
Names & identifiers
- Preferred name
- Propiomazine
- IUPAC
- 1-[10-[2-(dimethylamino)propyl]phenothiazin-2-yl]propan-1-one
- English name
- propiomazine
- Molecular formula
- C20H24N2OS
- Molecular weight
- 340.48
Names & synonyms
propiomazine362-29-8PropionylpromethazinePhenoctylPropiomazinaPropiomazinumWy-13591-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}propan-1-oneCB 16782-Propionyl-10-(2-(dimethylamino)propyl)phenothiazine3-Propionyl-10-dimethylaminoisopropylphenothiazine10-(2-Dimethylaminopropyl)-2-propionylphenothiazine
Show more names
(±)-Propiomazinepropiomazine USP/EP/BP1-[10-[2-(Dimethylamino)propyl]phenothiazin-2-yl-1-propanone1-[10-[2-(dimethylamino)propyl]phenothiazin-2-yl]propan-1-one1-[10-[2-(Dimethylamino)propyl]-10H-phenothiazin-2-yl]propan-1-one1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}-1-propanone1-Propanone, 1-[10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-
DorevanPropavanCB-1678DorevaneIndorm10-Dimethylaminoisopropyl-2-propionylphenothiazine242Z0PM79Y1-Propanone, 1-(10-(2-(dimethylamino)propyl)-10H-phenothiazin-2-yl)-
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 48.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 441
Experimental & physicochemical properties
LogP
4.5
4.4
Solubility
SLOWLY OXIDIZED WHEN MOISTENED OR IN AQUEOUS SOLN ON PROLONGED EXPOSURE TO AIR &/OR LIGHT; 1 G SOL IN 4.5 ML WATER; FREELY SOL IN ALCOHOL; INSOL IN BENZENE /HYDROCHLORIDE/
7.03e-03 g/L
Human DrugsPharmaceuticals
Boiling Point235-245 °C @ 0.5 MM HG
Melting Point
MP: 160-161 °C; CRYSTALS FROM ISOPROPANOL /MALEATE/
MP: 201-206 °C /HYDROCHLORIDE/
MP: 240-242 °C /METHIODIDE/
Physical DescriptionSolid
Other Experimental PropertiesPRACTICALLY ODORLESS; YELLOW POWDER /HYDROCHLORIDE/
Physicochemical properties
- Boiling point
- 0.5 · bp0.5 235-245°
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, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Interactions
...ENHANCES EFFECT OF CNS DEPRESSANTS: HENCE, DOSE OF BARBITURATES GIVEN CONCOMITANTLY SHOULD BE REDUCED 1/2, DOSES OF MEPERIDINE & MORPHINE SHOULD BE REDUCED 1/4 TO 1/2. /HYDROCHLORIDE/
...ENHANCES ACTION OF...ANALGESICS & ANESTHETICS. /HYDROCHLORIDE/
.../REPORTED/ TO PROTECT EXPTL ANIMALS AGAINST HEPATOTOXIC EFFECTS OF CARBON TETRACHLORIDE...
PHYSOSTIGMINE WAS GIVEN TO 17 PT INLABOR PREVIOUSLY GIVEN SCOPOLAMINE ALONE OR MEPERIDINE & PROPIOMAZINE IN COMBINATION, TO ASCERTAIN ITS EFFECT ON REVERSING THE LOSS OF FETAL HEART RATE VARIABILITY. WITH MEPERIDINE & PROPIOMAZINE COMBINATION, REVERSION OCCURRED IN 10 PT.
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
Toxicity Summary
Propiomazine is an antagonist at types 1, 2, and 4 dopamine receptors, serotonin (5-HT) receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Its main use as a sedative is due to its antihistamine effect.
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Protein Binding81%
PharmacodynamicsAlthough propiomazine is a phenothiazine, it is not used as an antipsychotic. It posesses antihistamine effects and is mostly used as a sedative in treating insomnia.
Mechanism of Action
Propiomazine acts as an antagonist of dopamine 1, 2, and 4 receptors, serotonin (5-HT) receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Its main use as a sedative is due to its antihistamine effect.
...ALSO HAS AN ANTIEMETIC ACTION. /HYDROCHLORIDE/
Metabolism/Metabolites
Unknown, but most likely hepatic as with other phenothiazines.
Unknown, but most likely hepatic as with other phenothiazines.
Absorption, Distribution and Excretion
APPROX HALF OF METABOLITES OF COMMONLY USED PHENOTHIAZINES ARE FOUND IN URINE & REST IN FECES. ULTIMATE SOJOURN OF PHENOTHIAZINE DRUGS IN BODY IS EXCEEDINGLY LONG. 6 MO AFTER DISCONTINUATION OF THESE DRUGS, VARIOUS METABOLITES ARE DETECTABLE IN URINE. /PHENOTHIAZINES/
PHENOTHIAZINE TRANQUILIZERS CROSS PLACENTA RAPIDLY, & THEY HAVE BEEN MEASURED FOR MANY YR IN URINE & TISSUES OF NEONATES OF TREATED MOTHERS, BUT VERY LOW BLOOD LEVELS OF MOTHERS & FETUSES HAVE BEEN MEASURED ONLY RECENTLY... /PHENOTHIAZINES/
Cellular LocationsMembrane
Metabolite PathwaysPropiomazine H1-Antihistamine Action
Uses & manufacturing
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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