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MedKoo Cat#: 598738 | Name: Levoprotiline

Description:

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

Levoprotiline is an antidepressive agent.

Chemical Structure

Levoprotiline
CAS#76496-68-9

Theoretical Analysis

MedKoo Cat#: 598738

Name: Levoprotiline

CAS#: 76496-68-9

Chemical Formula: C20H23NO

Exact Mass: 293.1780

Molecular Weight: 293.41

Elemental Analysis: C, 81.87; H, 7.90; N, 4.77; O, 5.45

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Levoprotiline; Levoprotilinum;
IUPAC/Chemical Name
(R)-1-(9,10-ethanoanthracen-9(10H)-yl)-3-(methylamino)propan-2-ol
InChi Key
FDXQKWSTUZCCTM-ZUIJCZDSSA-N
InChi Code
InChI=1S/C20H23NO/c1-21-13-14(22)12-20-11-10-15(16-6-2-4-8-18(16)20)17-7-3-5-9-19(17)20/h2-9,14-15,21-22H,10-13H2,1H3/t14-,15?,20?/m1/s1
SMILES Code
O[C@@H](CNC)CC12C3=C(C=CC=C3)C(CC2)C4=CC=CC=C14
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levoprotiline is an antidepressive agent.
In vitro activity:
TBD
In vivo activity:
The effects of repeated administration of levoprotiline, a novel type of tetracyclic antidepressant on histamine H1, muscarinic acetylcholine and alpha 1-adrenergic receptors and the response of phosphoinositide hydrolysis (PI) stimulated by histamine in the cortex of the rat brain were investigated. This demonstrates that the repeated treatment with levoprotiline has prominent action on the regulation of histamine H1 receptors and PI response coupling to histamine H1 receptors in vivo. Reference: Jpn J Pharmacol. 1992 May;59(1):31-5. https://pubmed.ncbi.nlm.nih.gov/1324374/

Preparing Stock Solutions

The following data is based on the product molecular weight 293.41 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. Noguchi S, Inukai T. Repeated treatment with levoprotiline, a novel antidepressant, up-regulates histamine H1 receptors and phosphoinositide hydrolysis response in vivo. Jpn J Pharmacol. 1992 May;59(1):31-5. doi: 10.1254/jjp.59.31. PMID: 1324374.
In vitro protocol:
TBD
In vivo protocol:
1. Noguchi S, Inukai T. Repeated treatment with levoprotiline, a novel antidepressant, up-regulates histamine H1 receptors and phosphoinositide hydrolysis response in vivo. Jpn J Pharmacol. 1992 May;59(1):31-5. doi: 10.1254/jjp.59.31. PMID: 1324374.
1: Kaiser G, Ackermann R, Dieterle W, Reimann IW, Bieck PR. Pharmacokinetics of the antidepressant levoprotiline after intravenous and peroral administration in healthy volunteers. Biopharm Drug Dispos. 1992 Mar;13(2):83-93. PubMed PMID: 1550911. 2: Náhunek K, Svestka J, Cesková E, Rysánek R, Obrovská V, Misurec J, Wendt G. Position of levoprotiline in the treatment of acute endogenous depression. Act Nerv Super (Praha). 1989 Dec;31(4):280-1. PubMed PMID: 2638110. 3: Ackermann R, Kaiser G, Schueller F, Dieterle W. Determination of the antidepressant levoprotiline and its N-desmethyl metabolite in biological fluids by gas chromatography/mass spectrometry. Biol Mass Spectrom. 1991 Nov;20(11):709-16. PubMed PMID: 1799582. 4: Höschl C, Filip V, Bornová L, David I, Karen P, Seifertová D. [Results of a clinical trial of levoprotiline]. Cesk Psychiatr. 1992 Jun;88(2):97-105. Czech. PubMed PMID: 1505054. 5: Filip V, Höschl C, Karen P, Seifertová D, Bornová L, Prasková H, Prasko J. Predicting therapeutic results with levoprotiline and maprotiline in major depression: the role of the outcome criteria. Br J Psychiatry Suppl. 1993 Sep;(21):35-8. PubMed PMID: 8217066. 6: Herrmann WM, Schärer E, Wendt G, Delini-Stula A. Pharmaco-EEG profile of levoprotiline: second example to discuss the predictive value of pharmaco-electroencephalography in early human pharmacological evaluations of psychoactive drugs. Pharmacopsychiatry. 1991 Nov;24(6):206-13. PubMed PMID: 1812497. 7: Noguchi S, Okada M, Inukai T. Pharmacological profile of the new antidepressant levoprotiline. Arzneimittelforschung. 1992 Jun;42(6):787-94. PubMed PMID: 1418032. 8: Rysánek R, Mayer P, Náhunek K, Svestka J, Cesková E. Comparison of effect of levoprotiline and dosulepine on cardial functions. Act Nerv Super (Praha). 1989 Dec;31(4):283. PubMed PMID: 2638112. 9: Faltus F, Janecková E, Papezová H. Maintenance therapy with levoprotiline in anorexia nervosa and bulimia nervosa. Homeost Health Dis. 1991;33(5-6):290-1. PubMed PMID: 18265502. 10: Faltus F, Janecková E. Levoprotiline--function regulator of food and satiety centres? Act Nerv Super (Praha). 1989 Dec;31(4):282-3. PubMed PMID: 2638111. 11: David I, Filip V, Höschl C, Albrecht V, Palus M, Seifertová D, Prasková H. Dynamics of the effects of levoprotiline and maprotiline on EEG in patients with major depressive episodes (DSM-III-R). Cesk Psychiatr. 1993 Jun;89(3):123-9. Czech. PubMed PMID: 8353827. 12: Jedrychowski M, Hoffmann E, Bieck PR. A rapid and sensitive method for the quantitation of levoprotiline in human blood and plasma. J Pharm Biomed Anal. 1989;7(12):1897-901. PubMed PMID: 2490580. 13: Klimek V, Zak-Knapik J, Cannizzaro C. Changes in the rat brain 5-HT1A and 5-HT2 receptors after chronic administration of levoprotiline, (+)-oxaprotiline and other antidepressant drugs. Pol J Pharmacol Pharm. 1992 Nov-Dec;44(6):549-60. PubMed PMID: 1305956. 14: Noguchi S, Inukai T. Repeated treatment with levoprotiline, a novel antidepressant, up-regulates histamine H1 receptors and phosphoinositide hydrolysis response in vivo. Jpn J Pharmacol. 1992 May;59(1):31-5. PubMed PMID: 1324374. 15: Faltus F, Molcan J, Svestka J, Náhunek K, Mrna B, Zapletálek M, Krekule P, Janecková E, Koníková M, Pazdírek S, et al. Comparative study of levoprotiline and amitriptyline in endogenous depressions. Act Nerv Super (Praha). 1989 Dec;31(4):279-80. PubMed PMID: 2638109. 16: Schubert T, Müller WE. Levoprotiline ((-)-oxaprotiline) effects on inositol phosphate generation in human peripheral lymphocytes. J Neural Transm Gen Sect. 1991;84(1-2):141-6. PubMed PMID: 2054146. 17: Noguchi S, Fukuda Y, Inukai T. Possible contributory role of the central histaminergic system in the forced swimming model. Arzneimittelforschung. 1992 May;42(5):611-3. PubMed PMID: 1530672. 18: Delini-Stula A, Mogilnicka E. Single treatments with the antidepressant oxaprotiline and its (+) and (-) enantiomers increase behavioural responses to dopaminergic stimulation in the rat. J Neural Transm. 1988;71(2):91-8. PubMed PMID: 3346651. 19: Horne C, Spahn H, Mutschler E. Fluorimetric determination of levoprotiline in human plasma after thin-layer chromatographic or high performance liquid chromatographic separation. Arzneimittelforschung. 1987 Oct;37(10):1179-81. PubMed PMID: 3435591. 20: Delini-Stula A, Radeke E, van Riezen H. Enhanced functional responsiveness of the dopaminergic system--the mechanism of anti-immobility effects of antidepressants in the behavioural despair test in the rat. Neuropharmacology. 1988 Sep;27(9):943-7. PubMed PMID: 3185868.

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