10347-81-6

Basic information

• Product Name: Maprotiline hydrochloride
• Synonyms: 10-ethanoanthracene-9(10h)-propylamine,n-methyl-hydrochloride;ba34276;ciba34276ba;ciba34276hydrochloride;n-methyl-9,10-ethanoanthracene-9(10h)-propanaminehydrochloride;9-[GAMMA-METHYLAMINOPROPYL]-9,10-DIHYDRO-9,10-ETHANOANTHRACENE HYDROCHLORIDE;1-(3-METHYLAMINOPROPYL)DIBENZO[B,E]BICYCLO[2.2.2]OCTADIENE HYDROCHLORIDE;MAPROTILENE HYDROCHLORIDE
• CAS NO: 10347-81-6
• Molecular Formula: C₂₀H₂₃N*ClH
• Molecular Weight: 313.86
• EINECS: 233-758-8
• Product Categories: Active Pharmaceutical Ingredients;Chemical Amines;Amines;Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor
• Mol File: 10347-81-6.mol

Chemical Properties

• Melting Point: 230-232°C
• Boiling Point: 399.6 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: white/powder
• Vapor Pressure: 9.8E-08mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: H2O: 50 mg/mL
• Water Solubility: Soluble to 50mg/ml in water. Soluble in ethanol at 10mM
• Merck: 14,5748
• CAS DataBase Reference: Maprotiline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Maprotiline hydrochloride(10347-81-6)
• EPA Substance Registry System: Maprotiline hydrochloride(10347-81-6)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 7-16-36/37-45
• RIDADR: 3249
• WGK Germany: 3
• RTECS: KJ4555000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 10347-81-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Maprotiline hydrochloride is used as an antidepressant for the treatment of depression and anxiety disorders. It functions by inhibiting the reuptake of norepinephrine in the brain and peripheral tissues, thereby increasing the levels of this neurotransmitter and alleviating depressive symptoms.
Used in Hormonal Contraceptives:
Maprotiline hydrochloride is also used in combination with progesterone as an oral contraceptive. Its estrogenic properties, when used in conjunction with progesterone, help to prevent ovulation and fertilization, providing a method of birth control.
Used in Neuroprotection:
Maprotiline hydrochloride has been shown to block apoptosis of spiny neurons and inhibit the solute carrier family 6 member 2 (SLC6A2), which may have implications for neuroprotection and the treatment of neurodegenerative diseases.
Used in Antiviral Research:
Maprotiline (20 μM) has demonstrated the ability to prevent acid sphingomyelinase activation and subsequent ceramide release induced by infection with replication-deficient vesicular stomatitis virus pseudoviral particles (pp-VSV) presenting the severe acute respiratory coronavirus 2 (SARS-CoV-2) spike protein in Vero cells. This suggests potential applications in antiviral research and the development of treatments for viral infections.
Chemical Properties:
Maprotiline hydrochloride is a crystalline solid, which is an important characteristic for its formulation and use in pharmaceutical products.

Therapeutic Function

Antidepressant

Biological Activity

Selective noradrenalin re-uptake inhibitor.

InChI:InChI=1/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/t15-,20+;

Synthetic route

maprotiline hydrochloride (10347-81-6) + p-benzoquinone (106-51-4) → N-Methyl-3-(9,10-dihydro-9,10-ethano-anthr-9-yl)-propylamino-1,4-benzochinon

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	90%

maprotiline hydrochloride (10347-81-6) → Desmethylmaprotiline (5721-37-9)

Conditions	Yield
With human liver microsomes; NADPH-generating system In phosphate buffer at 37℃; for 0.25h; pH=7.4; Enzyme kinetics; Further Variations:; Solvents;

maprotiline hydrochloride (10347-81-6) → 2,5-Bis--1,4-benzochinon

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / CH2Cl2 / 24 h / Ambient temperature 2: CH2Cl2 / Ambient temperature View Scheme

Downstream Products

• 5721-37-9 Desmethylmaprotiline