(-)-10-(3-[DIMETHYLAMINO]-2-METHYLPROPYL)-2-METHOXY-PHENOTHIAZINE MALEATE SALT
Synonym(s):(−)-10-(3-[Dimethylamino]-2-methylpropyl)-2-methoxyphenothiazine;Levomeprazine
- CAS NO.:60-99-1
- Empirical Formula: C19H24N2OS
- Molecular Weight: 328.47
- MDL number: MFCD00869255
- EINECS: 200-495-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-23 13:36:13
What is (-)-10-(3-[DIMETHYLAMINO]-2-METHYLPROPYL)-2-METHOXY-PHENOTHIAZINE MALEATE SALT?
Absorption
Methotrimeprazine has an incomplete oral bioavailability, because it undergoes considerable first-pass-metabolism in the liver. Oral bioavailability is approximately 50 to 60%.
Toxicity
Symptoms of overdose include convulsions, spastic movements, and coma.
Originator
Levoprome ,Lederle,US,1966
The Uses of (-)-10-(3-[DIMETHYLAMINO]-2-METHYLPROPYL)-2-METHOXY-PHENOTHIAZINE MALEATE SALT
Analgesic
The Uses of (-)-10-(3-[DIMETHYLAMINO]-2-METHYLPROPYL)-2-METHOXY-PHENOTHIAZINE MALEATE SALT
(R)-Methotrimeprazine acts as an analgesic agent.
Background
A phenothiazine with pharmacological activity similar to that of both chlorpromazine and promethazine. It has the histamine-antagonist properties of the antihistamines together with central nervous system effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604)
Indications
For the treatment of psychosis, particular those of schizophrenia, and manic phases of bipolar disorder.
Definition
ChEBI: A member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively.
Manufacturing Process
95% sodamide (2.33 g) is added to a boiling solution of 3- methoxyphenthiazine (12 g) in anhydrous xylene (150 cc) and the mixture is heated with agitation under reflux for 1? hours. A solution of 1- dimethylamino-2-methyl-3-chloropropane (8.2 g) in anhydrous xylene (90 cc) is then run in over a period of 45 minutes while the reaction temperature is maintained and heating under reflux is continued for 18 hours.
After cooling, the reaction mixture is agitated with a mixture of water (40 cc) and a normal solution of methanesulfonic acid (70 cc), the xylene layer is removed and the acid liquors are washed with ether (200 cc). The aqueous phase is then made alkaline with sodium hydroxide (d = 1.33; 10 cc) and the liberated base is extracted with ether. The ethereal solution is dried over anhydrous potassium carbonate and concentrated at normal pressure. On distillation of the residue under reduced pressure 3-(3-methoxy-10- phenthiazinyl)-2-methyl-1-dimethylaminopropane (11.3 g) is obtained, MP 103°C, BP 182° to 191°C/0.15 mm Hg. The hydrochloride prepared in isopropanol melts at about 90°C.
brand name
Levoprome (Immunex).
Therapeutic Function
Analgesic
Pharmacokinetics
Methotrimeprazine is a phenothiazine with pharmacological activity similar to that of both chlorpromazine and promethazine. It has the histamine-antagonist properties of the antihistamines together with central nervous system effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604)
Metabolism
Hepatic. Methotrimeprazine is metabolized in the liver and degraded to a sulfoxid-, a glucuronid- and a demethyl-moiety.
Properties of (-)-10-(3-[DIMETHYLAMINO]-2-METHYLPROPYL)-2-METHOXY-PHENOTHIAZINE MALEATE SALT
Melting point: | 117°C |
Boiling point: | 468.0±45.0 °C(Predicted) |
Density | 1.0897 (rough estimate) |
refractive index | 1.5950 (estimate) |
storage temp. | Store at -20°C |
solubility | Chloroform (Slightly), Methanol (Very Slightly) |
pka | 9.32±0.28(Predicted) |
form | Solid |
color | White to Off-White |
Water Solubility | 20mg/L(25 ºC) |
Safety information for (-)-10-(3-[DIMETHYLAMINO]-2-METHYLPROPYL)-2-METHOXY-PHENOTHIAZINE MALEATE SALT
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. |
Computed Descriptors for (-)-10-(3-[DIMETHYLAMINO]-2-METHYLPROPYL)-2-METHOXY-PHENOTHIAZINE MALEATE SALT
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(R)-3-Aminobutanenitrile Hydrochloride 4-Aminotetrahydropyran-4-carbonitrile Hydrochloride 4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID HCL 4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID 1,4-Dioxa-8-azaspiro[4.5]decane 5-Bromo-2-nitropyridine SODIUM AAS SOLUTION ZINC AAS SOLUTION BUFFER SOLUTION PH 10.0(BORATE) GOOCH CRUCIBLE SINTERED AQUANIL 5 BERYLLIUM AAS SOLUTION SODIUM VALPROATE Diclofenac Sodium Methylcobalamin (vitamin B12) VILDAGLIPTIN ACICLOVIR AMOXICILLIN (AMOXYCILLIN) TRIHYDRATE Desloratidine Related compound B Folic Acid Impurity G Glycopyrronium Bromide EP Impurity I Eltrombopag N-Oxide Impurity Di-Nitroso Acyclovir Impurity K DLRD N-OxideRelated products of tetrahydrofuran
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