10347-81-6

Crystalline Solid

Antidepressant

estrogen, with progesterone as oral contraceptive

Selective noradrenalin re-uptake inhibitor.

Maprotiline is a tricyclic antidepressant. It binds to the norepinephrine transporter (NET; K_d = 11 nM) and is selective for NET over the serotonin (5-HT) and dopamine transporters (K_ds = 5,800 and 1,000 nM, respectively). Maprotiline also binds to the 5-HT receptor subtype 5-HT_2A (K_I = 51 nM), as well as histamine H₁, muscarinic acetylcholine, α₁-adrenergic, and dopamine D₂ receptors (K_ds = 2, 570, 90, and 350 nM, respectively). In vivo, maprotiline inhibits norepinephrine reuptake in rat brain and peripheral tissues. It reduces isolation-induced aggressive behavior and inhibits electrical foot-shock stimulation-induced belligerence in mice when administered at doses ranging from 3 to 10 mg/kg. Maprotiline (20 μM) prevents 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, an effect that can be overcome with exogenous application of C16 ceramide (Item No. 10681). Formulations containing maprotiline have been used in the treatment of depression and anxiety. This product is also available as an analytical reference material (Item Nos. 32702 | 33077).

Maprotiline hydrochloride ,Mylan

ChEBI: Maprotiline hydrochloride is a member of anthracenes.

9-(3-Hydroxypropyl)anthracene was prepared by reduction of 3-(9-anthryl) propionic acid with LiAlH4. By action of thionylchloride and then methylamine the 9-(3-hydroxypropyl)anthracene was converted to 9-(3-methylaminopropyl) anthracene. By addition of ethylene to 9-(3-methylaminopropyl)anthracene (at 150°C, a pressure of ethylene 50 atm, 24 hours) was obtained 3-(9,10- dihydro-9,10-ethanoanthracene-9-yl)-N-methylpropylamine. Hydrochloride 3- (9,10-dihydro-9,10-ethanoanthracene-9-yl)-N-methylpropylamine may be prepared by action hydrochloric acid.

Antidepressant

Maprotiline hydrochloride, N-methyl-9,10-ethanoanthracene-9(10H)-propanamine hydrochloride (Ludiomil), is sometimesdescribed as a tetracyclic rather than a tricyclic antidepressant.The description is chemically accurate, but the compound,nonetheless, conforms to the overall TCA pharmacophore. Itis a dibenzobicyclooctadiene and can be viewed as a TCAwith an ethylene-bridged central ring. The compound is notstrongly anticholinergic and has stimulant properties. It canhave effects on the cardiovascular system. It is a SNERI.