Maprotiline Hydrochlorine
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MedKoo CAT#: 318172

CAS#: 10347-81-6 (HCl)

Description: Maprotiline Hydrochloride is the hydrochloride salt form of maprotiline, a tetracyclic antidepressant closely related to the tricyclic antidepressants with adrenergic activity and sedative properties. Maprotiline hydrochloride exerts its effect by blocking the re-uptake of norepinephrine, thereby increasing the synaptic concentration of norepinephrine in the central nervous system and subsequently prolonging the action of norepinephrine on central receptors.

Chemical Structure

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Maprotiline Hydrochlorine
CAS# 10347-81-6 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318172
Name: Maprotiline Hydrochlorine
CAS#: 10347-81-6 (HCl)
Chemical Formula: C20H24ClN
Exact Mass: 0.00
Molecular Weight: 313.869
Elemental Analysis: C, 76.53; H, 7.71; Cl, 11.30; N, 4.46

Price and Availability

Size Price Availability Quantity
1g USD 450 2 weeks
2g USD 750 2 Weeks
5g USD 1450 2 weeks
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Related CAS #: 10347-81-6 (HCl)   10262-69-8 (free base)   58902-67-3 (mesylate)   1329496-63-0 (d3   HCl)  

Synonym: Maprotiline Hydrochlorine;Maprotiline Hcl; Psymion; Ludiomil; Maprotilline HCl; Teva Brand of Maprotiline Hydrochloride;

IUPAC/Chemical Name: 9-(γ-Methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene hydrochloride

InChi Key: NZDMFGKECODQRY-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H23N.ClH/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20;/h2-5,7-10,15,21H,6,11-14H2,1H3;1H

SMILES Code: CNCCCC1(CC2)C3=CC=CC=C3C2C4=C1C=CC=C4.Cl

Appearance: White to off-white 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, not in water

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: Maprotiline hydrochloride is a selective noradrenalin re-uptake inhibitor and a tetracyclic antidepressant.
In vitro activity: Maprotiline is a tetracyclic antidepressant and possesses a highly selective norepinephrine reuptake ability. This study found that maprotiline decreased cell viability in a concentration- and time-dependent manner in Neuro-2a cells. Maprotiline induced apoptosis and increased caspase-3 activation. Reference: Toxicology. 2013 Feb 8;304:1-12. https://pubmed.ncbi.nlm.nih.gov/23219590/
In vivo activity: The anti-inflammatory effect of systemic maprotiline (12.5, 25 and 50 mg kg(-1)) was assessed using a rat paw edema model. Systemic, intracerebroventricular and subplantar application of maprotiline significantly inhibited peripheral edema, but intrathecal maprotiline did not alter the degree of paw swelling. Reference: Inflamm Res. 2010 Dec;59(12):1053-9. https://pubmed.ncbi.nlm.nih.gov/20574769/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Ethanol 19.5 62.13
PBS (pH 7.2) 0.1 0.32
Water 2.2 7.01

Preparing Stock Solutions

The following data is based on the product molecular weight 313.87 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. Chen W, Liu P, Liu D, Huang H, Feng X, Fang F, Li L, Wu J, Liu L, Solow-Cordero DE, Hu Y. Maprotiline restores ER homeostasis and rescues neurodegeneration via Histamine Receptor H1 inhibition in retinal ganglion cells. Nat Commun. 2022 Nov 10;13(1):6796. doi: 10.1038/s41467-022-34682-y. PMID: 36357388; PMCID: PMC9649812. 2. Jan CR, Su JA, Teng CC, Sheu ML, Lin PY, Chi MC, Chang CH, Liao WC, Kuo CC, Chou CT. Mechanism of maprotiline-induced apoptosis: role of [Ca2+](i), ERK, JNK and caspase-3 signaling pathways. Toxicology. 2013 Feb 8;304:1-12. doi: 10.1016/j.tox.2012.11.013. Epub 2012 Dec 3. PMID: 23219590. 3. Hajhashemi V, Sadeghi H, Minaiyan M, Movahedian A, Talebi A. Central and peripheral anti-inflammatory effects of maprotiline on carrageenan-induced paw edema in rats. Inflamm Res. 2010 Dec;59(12):1053-9. doi: 10.1007/s00011-010-0225-1. Epub 2010 Jun 24. PMID: 20574769. 4. Parra A, Martos A, Monleón S, Carmen Arenas M, Vinader-Caerols C. Effects of acute and chronic maprotiline administration on inhibitory avoidance in male mice. Behav Brain Res. 2000 Apr;109(1):1-7. doi: 10.1016/s0166-4328(99)00149-7. PMID: 10699652.
In vitro protocol: 1. Chen W, Liu P, Liu D, Huang H, Feng X, Fang F, Li L, Wu J, Liu L, Solow-Cordero DE, Hu Y. Maprotiline restores ER homeostasis and rescues neurodegeneration via Histamine Receptor H1 inhibition in retinal ganglion cells. Nat Commun. 2022 Nov 10;13(1):6796. doi: 10.1038/s41467-022-34682-y. PMID: 36357388; PMCID: PMC9649812. 2. Jan CR, Su JA, Teng CC, Sheu ML, Lin PY, Chi MC, Chang CH, Liao WC, Kuo CC, Chou CT. Mechanism of maprotiline-induced apoptosis: role of [Ca2+](i), ERK, JNK and caspase-3 signaling pathways. Toxicology. 2013 Feb 8;304:1-12. doi: 10.1016/j.tox.2012.11.013. Epub 2012 Dec 3. PMID: 23219590.
In vivo protocol: 1. Hajhashemi V, Sadeghi H, Minaiyan M, Movahedian A, Talebi A. Central and peripheral anti-inflammatory effects of maprotiline on carrageenan-induced paw edema in rats. Inflamm Res. 2010 Dec;59(12):1053-9. doi: 10.1007/s00011-010-0225-1. Epub 2010 Jun 24. PMID: 20574769. 2. Parra A, Martos A, Monleón S, Carmen Arenas M, Vinader-Caerols C. Effects of acute and chronic maprotiline administration on inhibitory avoidance in male mice. Behav Brain Res. 2000 Apr;109(1):1-7. doi: 10.1016/s0166-4328(99)00149-7. PMID: 10699652.

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1: Schwartz L, Swaminathan S. Maprotiline hydrochloride and convulsions: a case report. Am J Psychiatry. 1982 Feb;139(2):244-5. PubMed PMID: 6798885.

2: Wells BG, Gelenberg AJ. Chemistry, pharmacology, pharmacokinetics, adverse effects, and efficacy of the antidepressant maprotiline hydrochloride. Pharmacotherapy. 1981 Sep-Oct;1(2):121-39. PubMed PMID: 6765485.

3: Atri PB, Julius DA. Maprotiline hydrochloride associated with a clinical state of catatonic stupor and epileptic encephalogram. J Clin Psychopharmacol. 1984 Aug;4(4):207-9. PubMed PMID: 6470193.

4: Multicenter evaluation of maprotiline hydrochloride for treatment of depression. Clin Ther. 1984;6(2):155-62. PubMed PMID: 6367987.

5: Treatment of depression with maprotiline hydrochloride: multicenter evaluation of efficacy and tolerability. Clin Ther. 1983;5(4):377-84. PubMed PMID: 6347381.