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  • CL 36467
  • CL 39743
  • N05AA02
  • RP 7044
  • RP-7044
  • SK&F 5116
  • XP-03
  • XP03

Product Ingredients

Methotrimeprazine hydrochloride 42BB1Y2586 1236-99-3 ODLGFPIWRAEFAN-PFEQFJNWSA-N
Methotrimeprazine maleate 5KN5Y9V01K 7104-38-3 IFLZPECPTYCEBR-VIEYUMQNSA-N
CAS Registry Number: 60-99-1
CAS Name: (bR)-2-Methoxy-N,N,b-trimethyl-10H-phenothiazine-10-propanamine
Additional Names: (-)-10-(3-dimethylamino-2-methylpropyl)-2-methoxyphenothiazine; levomepromazine; 2-methoxytrimeprazine; levomeprazine
Manufacturers’ Codes: RP-7044
Trademarks: Sinogan-Debil; Tisercin (EGYT); Neozine (Rh>e-Poulenc); Nirvan; Nozinan (Rh>e-Poulenc); Levoprome (Lederle)
Molecular Formula: C19H24N2OS
Molecular Weight: 328.47
Percent Composition: C 69.47%, H 7.36%, N 8.53%, O 4.87%, S 9.76%
Literature References: Prepn: Courvoisier et al., C.R. Seances Soc. Biol. Ses Fil. 151, 1378 (1957); Jacob, Robert, US 2837518 (1958 to Rhône-Poulenc).
Optical Rotatory Power, -17, Conc: 5 g/100mL; Solv: chloroform; Wavlen: 589.3 nm; Temp: 20 °C
Derivative Type: Maleate
CAS Registry Number: 7104-38-3
Trademarks: Minozinan; Milezin (Spofa); Neuractil; Neurocil (Bayer); Sofmin (Dainippon); Veractil
Molecular Formula: C19H24N2OS.C4H4O4
Molecular Weight: 444.54
Percent Composition: C 62.14%, H 6.35%, N 6.30%, O 18.00%, S 7.21%
Properties: Crystals, darkened by light. Dec about 190°. Sparingly sol in water (0.3% at 20°) and in ethanol (0.4%). pH of a 0.3% aq soln is 4.3. The free base is levorotatory: [a]D20 -17° (c = 5 in chloroform).
Optical Rotation: [a]D20 -17° (c = 5 in chloroform)
Therap-Cat: Analgesic.
Keywords: Analgesic (Non-Narcotic).

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Methotrimeprazine is a phenothiazine used in the management of psychosis, particular those of schizophrenia, and manic phases of bipolar disorder.

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)

Levomepromazine, also known as methotrimeprazine, is a phenothiazine neuroleptic drug. Brand names include Nozinan, Levoprome, Detenler, Hirnamin, Levotomin and Neurocil. It is a low-potency antipsychotic (approximately half as potent as chlorpromazine) with strong analgesichypnotic and antiemetic properties that are primarily used in palliative care.[1][2]

Serious side effects include tardive dyskinesiaakathisiaabnormalities in the electrical cycle of the heartlow blood pressure and the potentially fatal neuroleptic malignant syndrome.[1][2]

As is typical of phenothiazine antipsychotics, levomepromazine is a “dirty drug“, that is, it exerts its effects by blocking a variety of receptors, including adrenergic receptorsdopamine receptorshistamine receptorsmuscarinic acetylcholine receptors and serotonin receptors.[1][2]

Medical uses

It can be used as an analgesic for moderate to severe pain in non-ambulant patients (the latter being because of its strong sedative effects).[3]

Levomepromazine is also used at lower doses for the treatment of nausea and insomnia.[1]

Levomepromazine is frequently prescribed and valued worldwide in palliative care medicine for its multimodal action, to treat intractable nausea or vomiting, and for severe delirium/agitation in the last days of life. Palliative care physicians will commonly prescribe it orally or via subcutaneous syringe drivers in combination with opioid analgesics such as hydromorphone.[1][2]

Levomepromazine is used for the treatment of psychosis, particularly those of schizophrenia, and manic phases of bipolar disorder. It should only be used with caution in the treatment of agitated depressions, as it can cause akathisia as a side effect, which could worsen the agitation.[1][2] A 2010 systematic review compared the efficacy of levomepromazine with atypical antipsychotic drugs:

Levomepromazine versus atypical antipsychotic drugs for schizophrenia[4]

Adverse effects

The most common side effect is akathisia.[2] Levomepromazine has prominent sedative and anticholinergic/sympatholytic effects (dry mouth, hypotensionsinus tachycardia, night sweats) and may cause weight gain.[2] These side effects normally preclude prescribing the drug in doses needed for full remission of schizophrenia, so it has to be combined with a more potent antipsychotic.[2] In any case, blood pressure and EKG should be monitored regularly.[2]

A rare but life-threatening side effect is neuroleptic malignant syndrome (NMS).[2] The symptoms of NMS include muscle stiffness, convulsions and fever.[2]


Bulletin de la Societe de Pharmacie de Bordeaux (1964), 103(4), 224-30.

The authors define an extn. equil. const., pKe.  When a basic mol., A, in an org. solvent (immiscible with water) is shaken with an aq. acid, part of A passes into the aq. phase in the equil. A + H+ .rdblhar. AH+, and Ke and pKe are defined by the equations Ke = [A]org[H+]H2O/[AH+]H2O and pKe = pKa -log ([A]org/[A]H2O), resp.  Values of pKe are reported for levomepromazine, properidiazine, thioridazine, chlorpromazine, alimenazine, propiomazine, promethazine, and aminopromazine.  Where 2 C atoms sep. the 2 N chain atoms, pKe is of the order of 5, and if 3, the value is near 4.3.


JP 40009030

A soln. of 10.5 g.  l-3-dimethylamino-2-methylpropanol in xylene is added a suspension of 2.5 g. Na in xylene and a soln. of 18 g. p-tosyl chloride in xylene is dropped in to give l-3-dimethylamino-2-methylpropanol tosylate (I), hydrochloride m. 98-100%.  I is treated with 18 g. 2-methoxyphenothiazine and NaNH2 (prepd. from 1.85 g. Na) to give 80% l-3-(2-methoxy-10-phenothiazinyl)-2-methyl-1-dimethylaminopropane, m. 125-6° (hexane).  Similarly are prepd. l-3-(3-ethyl-10-phenothiazinyl)-2-methyl-1-dimethylaminopropane (maleate m. 136°) and l-3-(10-phenothiazinyl)-2-methyl-1-dimethylaminopropane (maleate m. 174-5°).  The products are tranquilizers.


HU 152208

HU 157158

PL 66636


Bulletin de la Societe Chimique de France (1968), (8), 3220-2.

Folia medica (1970), 12(1), 88-9

Journal of pharmaceutical sciences (1987), 76(7), 541-4.



Deprotonation of 2-methoxyphenothiazine by means of KOH in refluxing touene/DMSO, followed by condensation of resulting pottasium salt with N-(3-chloro-2-methylpropyl)-N,N-dimethylamine  in refluxing toluene leads to racemic levomepromazine , which upon finally resolution using (-)-dibenzoyl-L-tartaric acid in acetone or using di-p-toluoyl-L-tartaric acid and, optionally, HCOOH in EtOH at 60 °C affords the target levomepromazine



  1. Jump up to:a b c d e f Brayfield A, ed. (13 December 2013). “Levomepromazine”Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 12 May 2014.
  2. Jump up to:a b c d e f g h i j k Joint Formulary Committee (2013). British National Formulary (BNF) (65 ed.). London, UK: Pharmaceutical Press. ISBN 978-0-85711-084-8.
  3. ^ “Levomepromazine”Farmacotherapeutisch Kompas (in Dutch). Retrieved 5 October 2016.
  4. Jump up to:a b Sivaraman P, Rattehalli RD, Jayaram MB (October 2010). “Levomepromazine for schizophrenia”The Cochrane Database of Systematic Reviews10 (10): CD007779. doi:10.1002/14651858.CD007779.pub2PMC 3283151PMID 20927765.

External links

Clinical data
AHFS/ Micromedex Detailed Consumer Information
  • Only if clearly needed
Routes of
Oral, seldom IM
Drug class Typical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability ~50–60%
Metabolism Hepatic
Elimination half-life ~20 hours
Excretion In feces and urine (metabolites), unchanged drug only 1%
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.450 Edit this at Wikidata
Chemical and physical data
Formula C19H24N2OS
Molar mass 328.47 g·mol−1
3D model (JSmol)
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///////////methotripremazine, L 36467, CL 39743, N05AA02, RP 7044, RP-7044, SK&F 5116, XP-03, XP03


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