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MedKoo Cat#: 525437 | Name: Levomepromazine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levomepromazine, also known as methotrimeprazine, is a phenothiazine neuroleptic drug. Levomepromazine is used for the treatment of psychosis, particularly those of schizophrenia, and manic phases of bipolar disorder.

Chemical Structure

Levomepromazine
Levomepromazine
CAS#60-99-1

Theoretical Analysis

MedKoo Cat#: 525437

Name: Levomepromazine

CAS#: 60-99-1

Chemical Formula: C19H24N2OS

Exact Mass: 328.1609

Molecular Weight: 328.47

Elemental Analysis: C, 69.47; H, 7.36; N, 8.53; O, 4.87; S, 9.76

Price and Availability

Size Price Availability Quantity
200mg USD 750.00
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Related CAS #
1236-99-3 (HCl) 60-99-1 (free base) 7104-38-3 (maleate)
Synonym
Levomepromazine; Levomepromazin; Levomepromazinum; Mepromazine; Methotrimeprazine; Methoxytrimeprazine; Milezin; Minozinan; Neozine; Neurocil.
IUPAC/Chemical Name
(-)-(2R)-3-(2-Methoxy-10H-phenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
InChi Key
VRQVVMDWGGWHTJ-CQSZACIVSA-N
InChi Code
InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1
SMILES Code
C[C@@H](CN1c2ccccc2Sc3c1cc(cc3)OC)CN(C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levomepromazine (Methotrimeprazine) is an orally available neuroleptic agent, which is commonly used to relieve nausea and vomiting in palliative care settings. Levomepromazine has antagonist actions at multiple neurotransmitter receptor sites, including dopaminergic, cholinergic, serotonin and histamine receptors.
In vitro activity:
The results indicate that levomepromazine and clozapine induce the expression of main CYP enzyme CYP3A4 in human hepatocytes. Levomepromazine and clozapine at concentrations of 2.5 and 10 µM, respectively, caused a significant increase in the mRNA level and activity of CYP3A4. Reference: Pharmacol Rep. 2021 Feb;73(1):303-308. https://pubmed.ncbi.nlm.nih.gov/32888176/
In vivo activity:
In vivo, LMP's (levomepromazine) effects were first assessed in 5-day-old healthy, uninjured CD-1 mouse pups receiving a single intraperitoneal injection of vehicle or different dosages of LMP. In vivo, no specific toxic effects of LMP were observed neither in healthy mouse pups nor in experimental animals subjected to excitotoxic injury, but body weight gain was significantly lower following higher-dose LMP treatment. Reference: IBRO Rep. 2020 Sep 24;9:247-257. https://pubmed.ncbi.nlm.nih.gov/33024879/
Solvent mg/mL mM
Solubility
DMSO 41.7 126.86
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 328.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Danek PJ, Basińska-Ziobroń A, Wójcikowski J, Daniel WA. Levomepromazine and clozapine induce the main human cytochrome P450 drug metabolizing enzyme CYP3A4. Pharmacol Rep. 2021 Feb;73(1):303-308. doi: 10.1007/s43440-020-00157-4. Epub 2020 Sep 4. PMID: 32888176; PMCID: PMC7862537. 2. Posod A, Winkler I, Wegleiter K, Huber E, Urbanek M, Kiechl-Kohlendorfer U, Griesmaier E. The effect of levomepromazine on the healthy and injured developing mouse brain - An in vitro and in vivo study. IBRO Rep. 2020 Sep 24;9:247-257. doi: 10.1016/j.ibror.2020.09.003. PMID: 33024879; PMCID: PMC7527626.
In vitro protocol:
1. Danek PJ, Basińska-Ziobroń A, Wójcikowski J, Daniel WA. Levomepromazine and clozapine induce the main human cytochrome P450 drug metabolizing enzyme CYP3A4. Pharmacol Rep. 2021 Feb;73(1):303-308. doi: 10.1007/s43440-020-00157-4. Epub 2020 Sep 4. PMID: 32888176; PMCID: PMC7862537.
In vivo protocol:
1. Posod A, Winkler I, Wegleiter K, Huber E, Urbanek M, Kiechl-Kohlendorfer U, Griesmaier E. The effect of levomepromazine on the healthy and injured developing mouse brain - An in vitro and in vivo study. IBRO Rep. 2020 Sep 24;9:247-257. doi: 10.1016/j.ibror.2020.09.003. PMID: 33024879; PMCID: PMC7527626.
1: Gál GT, May NV, Bombicz P. Crystal structure of levomepromazine maleate. Acta Crystallogr E Crystallogr Commun. 2016 Apr 5;72(Pt 5):612-5. doi: 10.1107/S2056989016004916. eCollection 2016 May 1. PubMed PMID: 27308001; PubMed Central PMCID: PMC4908531. 2: Cox L, Darvill E, Dorman S. Levomepromazine for nausea and vomiting in palliative care. Cochrane Database Syst Rev. 2015 Nov 2;(11):CD009420. doi: 10.1002/14651858.CD009420.pub3. Review. PubMed PMID: 26524693. 3: Basińska-Ziobroń A, Daniel WA, Wójcikowski J. Inhibition of human cytochrome P450 isoenzymes by a phenothiazine neuroleptic levomepromazine: An in vitro study. Pharmacol Rep. 2015 Dec;67(6):1178-82. doi: 10.1016/j.pharep.2015.04.005. Epub 2015 Apr 23. PubMed PMID: 26481538. 4: Wójcikowski J, Basińska A, Boksa J, Daniel WA. The influence of amitriptyline and carbamazepine on levomepromazine metabolism in human liver: an in vitro study. Pharmacol Rep. 2014 Dec;66(6):1122-6. doi: 10.1016/j.pharep.2014.07.012. Epub 2014 Aug 7. PubMed PMID: 25443744. 5: Wójcikowski J, Basińska A, Daniel WA. The cytochrome P450-catalyzed metabolism of levomepromazine: a phenothiazine neuroleptic with a wide spectrum of clinical application. Biochem Pharmacol. 2014 Jul 15;90(2):188-95. doi: 10.1016/j.bcp.2014.05.005. Epub 2014 May 16. PubMed PMID: 24841887. 6: Suzuki H, Gen K, Takahashi Y. A naturalistic comparison study of the efficacy and safety of intramuscular olanzapine, intramuscular haloperidol, and intramuscular levomepromazine in acute agitated patients with schizophrenia. Hum Psychopharmacol. 2014 Jan;29(1):83-8. doi: 10.1002/hup.2376. PubMed PMID: 24424709. 7: Preßler J, Lücking M, Melter M, Gerling S. Nonsustained ventricular tachycardia in a patient with acquired long QT syndrome after levomepromazine injection. Intensive Care Med. 2014 Jan;40(1):133-4. doi: 10.1007/s00134-013-3138-y. Epub 2013 Oct 30. PubMed PMID: 24170144. 8: Suzuki H, Gen K. A naturalistic comparison of the efficacy and safety of intramuscular olanzapine and intramuscular levomepromazine in agitated elderly patients with schizophrenia. Neuropsychiatr Dis Treat. 2013;9:1281-7. doi: 10.2147/NDT.S50754. Epub 2013 Aug 28. PubMed PMID: 24039430; PubMed Central PMCID: PMC3770645. 9: Piñero-Santiago LE, García C, Lhiaubet-Vallet V, Trzcionka J, Oyola R, Torres K, Leguillú J, Miranda MA. Photooxidation mechanism of levomepromazine in different solvents. Photochem Photobiol. 2013 Nov-Dec;89(6):1479-89. doi: 10.1111/php.12147. Epub 2013 Sep 10. PubMed PMID: 23909411. 10: Darvill E, Dorman S, Perkins P. Levomepromazine for nausea and vomiting in palliative care. Cochrane Database Syst Rev. 2013 Apr 30;(4):CD009420. doi: 10.1002/14651858.CD009420.pub2. Review. Update in: Cochrane Database Syst Rev. 2015;(11):CD009420. PubMed PMID: 23633372. 11: Fernandez-Campos F, Mallandrich M, Calpena AC, Ayestarán A, Lacasa C. Stability studies of binary and ternary mixtures containing morphine, midazolam, levomepromazine and hyoscine butylbromide for parenteral administration. J Pharm Pharmacol. 2013 Mar;65(3):379-89. doi: 10.1111/jphp.12001. Epub 2013 Jan 14. PubMed PMID: 23356847. 12: Dietz I, Schmitz A, Lampey I, Schulz C. Evidence for the use of Levomepromazine for symptom control in the palliative care setting: a systematic review. BMC Palliat Care. 2013 Jan 19;12:2. doi: 10.1186/1472-684X-12-2. PubMed PMID: 23331515; PubMed Central PMCID: PMC3602665. 13: Murray-Brown FL. A case of possible glossitis in a patient with non small cell carcinoma of the lung secondary to levomepromazine. Palliat Med. 2012 Sep;26(6):860-1. doi: 10.1177/0269216311434953. PubMed PMID: 22918478. 14: Karpińska J, Sokół A, Bernatowicz A, Szulęcka A, Kotowska U. Studies on photodegradation of levomepromazine and olanzapine under simulated environmental conditions. Photochem Photobiol Sci. 2012 Oct;11(10):1575-84. PubMed PMID: 22859061. 15: Mizoguchi Y. Levomepromazine-induced retrograde ejaculation. J Neuropsychiatry Clin Neurosci. 2012 Winter;24(1):E32. doi: 10.1176/appi.neuropsych.11020049. PubMed PMID: 22450639. 16: Sivaraman P, Rattehalli R, Jayaram M. Levomepromazine for schizophrenia. Schizophr Bull. 2012 Mar;38(2):219-20. doi: 10.1093/schbul/sbr174. Epub 2011 Nov 23. Review. PubMed PMID: 22114097; PubMed Central PMCID: PMC3283151. 17: Al-Tannak NF, Cable CG, McArthur DA, Watson DG. A stability indicating assay for a combination of morphine sulphate with levomepromazine hydrochloride used in palliative care. J Clin Pharm Ther. 2012 Feb;37(1):71-3. doi: 10.1111/j.1365-2710.2011.01252.x. Epub 2011 Mar 16. PubMed PMID: 21410738. 18: Hardy J, O'Shea A, Gilbert C, Norris R. Is levomepromazine stable over time? Palliat Med. 2011 Apr;25(3):284-5. doi: 10.1177/0269216310387963. Epub 2011 Jan 19. PubMed PMID: 21248181. 19: Sivaraman P, Rattehalli RD, Jayaram MB. Levomepromazine for schizophrenia. Cochrane Database Syst Rev. 2010 Oct 6;(10):CD007779. doi: 10.1002/14651858.CD007779.pub2. Review. PubMed PMID: 20927765. 20: Tanii H, Saka K, Inoue K, Okada M. Neuroleptic malignant syndrome following levomepromazine discontinuation. J Neuropsychiatry Clin Neurosci. 2010 Spring;22(2):E16. doi: 10.1176/appi.neuropsych.22.2.247-j.e16. PubMed PMID: 20463130.

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