| Identification | Back Directory | [Name]
Maprotiline hydrochloride | [CAS]
10347-81-6 | [Synonyms]
ba34276
Psymion
Maprolu
Deprilept
ciba34276ba
LUDIOMIL HCL
Ludiomil tab
Einecs 233-758-8
Ludiomil comprimes
ciba34276hydrochloride
MAPROTILENE HYDROCHLORIDE
MAPROTILINE HYDROCHLORIDE
Maprotiline Hydrochloride (200 mg)
Maprotiline hydrochloride solution
Maprotiline, LudioMil Hydrochloride
10-ethanoanthracene-9(10h)-propylamine,n-methyl-hydrochloride
n-methyl-9,10-ethanoanthracene-9(10h)-propanaminehydrochloride
N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine Hydrochloride
9,10-Ethanoanthracene-9(10H)-propanamine, N-methyl-, hydrochloride
9,10-Ethanoanthracene-9(10H)-propylamine, N-methyl-, hydrochloride
N-methyl-9,10-ethanoanthracene-9(10H)-propanamine,hydrochloride (1:1)
9-(γ-methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene hydrochloride
1-(3-METHYLAMINOPROPYL)DIBENZO[B,E]BICYCLO[2.2.2]OCTADIENE HYDROCHLORIDE
9-[GAMMA-METHYLAMINOPROPYL]-9,10-DIHYDRO-9,10-ETHANOANTHRACENE HYDROCHLORIDE
Maprotiline hydrochloride,9-(γ-Methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene hydrochloride | [EINECS(EC#)]
233-758-8 | [Molecular Formula]
C20H24ClN | [MDL Number]
MFCD00079464 | [MOL File]
10347-81-6.mol | [Molecular Weight]
313.86 |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
230-232°C | [Fp ]
9℃ | [storage temp. ]
Store at RT | [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 | [Major Application]
pharmaceutical (small molecule) | [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+; | [InChIKey]
NZDMFGKECODQRY-ZLYMRNBRNA-N | [SMILES]
[C@@]12(CCCNC)CC[C@@]([H])(C3C=CC=CC1=3)C1C=CC=CC2=1.Cl |&1:0,8,r| |
| Questions And Answer | Back Directory | [Preparation]
The traditional synthesis of maprotiline hydrochloride mainly uses anthrone as a starting material, and proceeds through reactions such as cyanoethylation, hydrolysis, selective reduction, addition cyclization, amidation, and reduction. |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Uses]
Antidepressant | [Uses]
estrogen, with progesterone as oral contraceptive | [Biological Activity]
Selective noradrenalin re-uptake inhibitor. | [Description]
Maprotiline is a tricyclic antidepressant.1,2 It binds to the norepinephrine transporter (NET; Kd = 11 nM) and is selective for NET over the serotonin (5-HT) and dopamine transporters (Kds = 5,800 and 1,000 nM, respectively).2 Maprotiline also binds to the 5-HT receptor subtype 5-HT2A (KI = 51 nM), as well as histamine H1, muscarinic acetylcholine, α1-adrenergic, and dopamine D2 receptors (Kds = 2, 570, 90, and 350 nM, respectively).3 In vivo, maprotiline inhibits norepinephrine reuptake in rat brain and peripheral tissues.4 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).5 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). | [Originator]
Maprotiline hydrochloride ,Mylan | [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. | [References]
[1] THOMAS KELLER Ulrich Z. Gas chromatographic examination of postmortem specimens after maprotiline intoxication[J]. Forensic science international, 1997, 88 2: Pages 117-123. DOI: 10.1016/s0379-0738(97)00064-9
[2] R M PINDER. Maprotiline: a review of its pharmacological properties and therapeutic efficacy in mental depressive states.[J]. Drugs, 1977, 13 5: 321-352. DOI: 10.2165/00003495-197713050-00001 |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P301+P312+P330 | [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 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
LD50 in mice, rats (mg/kg): ~750, ~900 orally (Hess) |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
|