(±)-Propiomazine
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(±)-Propiomazine
structure -
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CAS No:
362-29-8
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Formula:
C20H24N2OS
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Chemical Name:
(±)-Propiomazine
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Synonyms:
1-Propanone,1-[10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-;1-Propanone,1-[10-[2-(dimethylamino)propyl]phenothiazin-2-yl]-;1-[10-[2-(Dimethylamino)propyl]-10H-phenothiazin-2-yl]-1-propanone;1-[10-[2-(Dimethylamino)propyl]phenothiazin-2-yl]-1-propanone;Propiomazine;Propionylpromethazine;2-Propionyl-10-[2-(dimethylamino)propyl]phenothiazine;(±)-Propiomazine;Wy 1359;88245-06-1
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CAS No:
Description
ChEBI: 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.
Solid
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 phenothiazine antipsychotic drug, a dopaminergic antagonist, a serotonergic antagonist, a muscarinic antagonist, a histamine antagonist and a sedative. It is a member of phenothiazines, an aromatic ketone and a tertiary amino compound. It derives from a hydride of a 10H-phenothiazine.|Propiomazine, an atypical antipsychotic agent, is used to treat both negative and positive symptoms of schizophrenia, acute mania with bipolar disorder, agitation, and psychotic symptoms in dementia. Future uses may include the treatment of obsessive-compulsive disorder and severe behavioral disorders in autism. Structurally and pharmacologically similar to clozapine, propiomazine binds to alpha(1), dopamine, histamine H1, muscarinic, and serotonin type 2 (5-HT2) receptors.
Characteristics
48.8
4.5
Solid
1.137g/cm3
MP: 160-161 °C; CRYSTALS FROM ISOPROPANOL /MALEATE/|MP: 201-206 °C /HYDROCHLORIDE/|MP: 240-242 °C /METHIODIDE/
235-245 °C @ Press: 0.5 Torr
256.7ºC
7.03e-03 g/L
PRACTICALLY ODORLESS; YELLOW POWDER /HYDROCHLORIDE/
Safety Information
P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, P501
H302
Toxicity
Although rare, serious adverse events may be seen with propiomazine. Such events include convulsions (seizures), difficult or unusually fast breathing, fast or irregular heartbeat or pulse, fever (high), high or low blood pressure, loss of bladder control, muscle stiffness (severe), unusual increase in sweating, unusually pale skin, and unusual tiredness or weakness.
...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.
81%
Drug Information
Propiomazine is largely used for its antihistamininc sleep inducing effects in treating insomnia.
Antipsychotic Agents, Phenothiazine|A SUBSTITUTED PHENOTHIAZINE USED PRIMARILY FOR ITS SEDATIVE PROPERTIES. IT IS INDICATED FOR RELIEF OF RESTLESSNESS & APPREHENSION BEFORE & DURING SURGERY. IT IS ALSO USED AS ADJUNCT TO ANALGESICS FOR APPREHENSION & RESTLESSNESS DURING LABOR. /HYDROCHLORIDE/
PT SHOULD BE WARNED ABOUT PERFORMING HAZARDOUS TASKS WHILE ON THE DRUG. ITS SAFE USE DURING THE FIRST TRIMESTER OF PREGNANCY HAS NOT BEEN ESTABLISHED. UNTOWARD EFFECTS ARE USUALLY MILD & RESEMBLE THOSE INDUCED BY OTHER SEDATIVE PHENOTHIAZINES. /HYDROCHLORIDE/|SINCE SEVERE CHEMICAL IRRITATION MAY OCCUR WHEN PERIVASCULAR EXTRAVASATION OF SOLN OCCURS, CARE SHOULD BE EXERCISED WHEN IV ROUTE IS EMPLOYED. /HYDROCHLORIDE/
4(?). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (UMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OUNCE FOR 70 KG PERSON (150 LB). /HYDROCHLORIDE/
Although 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.
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/
Unknown, but most likely hepatic as with other phenothiazines.
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/
SEE PROMETHAZINE. ...CASE IS REPORTED OF 2-YR-OLD CHILD WHO INGESTED 250 MG WITH RESULTING CONFUSION, CONVULSIONS, & STUPOR, BUT EVENTUAL RECOVERY. /PROMETHAZINE/|PHENOTHIAZINES INHIBIT EJACULATION WITHOUT INTERFERING WITH ERECTION. /PHENOTHIAZINES/|MOST DANGEROUS EFFECTS OF PHENOTHIAZINES ARE THOSE RESULTING FROM HYPERSENSITIVITY REACTIONS, PARTICULARLY BLOOD DYSCRASIAS. THERAPEUTIC DOSES... MAY CAUSE FAINTNESS, PALPITATION, NASAL STUFFINESS, DRY MOUTH, & SOME SLIGHT CONSTIPATION. PT MAY COMPLAIN OF BEING COLD, DROWSY, OR WEAK. /PHENOTHIAZINES/|MOST TROUBLESOME SIDE EFFECT IS ORTHOSTATIC HYPOTENSION, WHICH MAY RESULT IN SYNCOPE. ... THERE IS GENERAL AGREEMENT THAT JAUNDICE FOLLOWING PHENOTHIAZINE ADMIN IS HYPERSENSITIVITY REACTION. ... LEUKOCYTOSIS, LEUKOPENIA, & EOSINOPHILIA OCCUR WITH PHENOTHIAZINE MEDICATION. /PHENOTHIAZINES/|For more Human Toxicity Excerpts (Complete) data for PROPIOMAZINE (8 total), please visit the HSDB record page.
Largon
(±)-Propiomazine Use and Manufacturing
SCHMITT ET AL, BULL SOC CHIM FRANCE 1957, 1474; SCHMITT, FRENCH PATENT ADDN 71,342 (ADDN TO FRENCH PATENT 1,176,919 TO CLI N-BYLA).|1-(PHENOTHIAZIN-2-YL)-1-PROPANONE IS CONDENSED WITH 2-(DIMETHYLAMINO)PROPYL CHLORIDE WITH THE AID OF A DEHYDROCHLORINATING AGENT SUCH AS SODAMIDE. THE PROPIOMAZINE THUS FORMED IS DISSOLVED IN A SUITABLE ORG SOLVENT & REACTED WITH AN EQUIMOLAR PORTION OF HYDROGEN CHLORIDE TO YIELD THE SALT. /HYDROCHLORIDE/
1-[10-[2-(Dimethylamino)propyl]phenothiazin-2-yl-1-propanone is used in the preparation of analgesics as well as maintaining its own analgesic effects whilst applied to various neurological diseases.
1678 CB, DOREVANE, INDORM, PROPAVAN. /MALEATE/|LARGON. /HYDROCHLORIDE/
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
Computed Properties
Molecular Weight:340.5
XLogP3:4.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:340.16093457
Monoisotopic Mass:340.16093457
Topological Polar Surface Area:48.8
Heavy Atom Count:24
Complexity:441
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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