Maprotiline hydrochloride Chemical Properties

Melting point:

230-232°C

Flash point:

9℃

storage temp. 

2-8°C

solubility 

H₂O: 50 mg/mL

form 

powder

color 

white

Water Solubility 

Soluble to 50mg/ml in water. Soluble in ethanol at 10mM

Merck 

14,5748

Safety Information

Hazard Codes 

Xn,T,F

Risk 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

HS Code 

2921490002

Toxicity

LD50 in mice, rats (mg/kg): ~750, ~900 orally (Hess)

MSDS

• Language:English Provider:SigmaAldrich

Maprotiline hydrochloride Usage And Synthesis

Description

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 . 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).

Chemical Properties

Crystalline Solid

Originator

Maprotiline hydrochloride ,Mylan

Uses

Antidepressant

Uses

estrogen, with progesterone as oral contraceptive

Uses

Maprotiline Hydrochloride has also been shown to block apoptosis of spiny neurons and inhibit SLC6A2.

Definition

ChEBI: Maprotiline hydrochloride is a member of anthracenes.

Manufacturing Process

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.

Therapeutic Function

Antidepressant

General Description

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.

Biological Activity

Selective noradrenalin re-uptake inhibitor.

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