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MIANSERIN

Product Name
MIANSERIN
CAS No.
24219-97-4
Chemical Name
MIANSERIN
Synonyms
Depnon;Org-4360;Org-5859;MIANSERIN;MIANSERINE;(S)-Mianserine;(R)-Mianserine;Mianserin USP/EP/BP;Mianserin Impurity 14;MIANSERIN,1.0MG/MLINMETHANOL
CBNumber
CB6679015
Molecular Formula
C18H20N2
Formula Weight
264.36
MOL File
24219-97-4.mol
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MIANSERIN Property

Boiling point:
397.6°C (rough estimate)
Density 
1.0092 (rough estimate)
refractive index 
1.5200 (estimate)
storage temp. 
Store at -20°C
solubility 
Soluble in DMSO
form 
Powder
pka
pKa 7.5(H2O,t =20.0) (Uncertain)
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Safety

RIDADR 
3249
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
24219-97-4(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
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N-Bromosuccinimide Price

ApexBio Technology
Product number
B1118
Product name
(R)-3-methyl-1,2,3,4,4a,9-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine
Packaging
100mg
Price
$151
Updated
2021/12/16
ApexBio Technology
Product number
B1118
Product name
(R)-3-methyl-1,2,3,4,4a,9-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine
Packaging
200mg
Price
$241
Updated
2021/12/16
ApexBio Technology
Product number
B1118
Product name
(R)-3-methyl-1,2,3,4,4a,9-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine
Packaging
500mg
Price
$387
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0000656
Product name
MIANSERIN
Purity
95.00%
Packaging
10MG
Price
$697.34
Updated
2021/12/16
AvaChem
Product number
1701B
Product name
Mianserin
Packaging
100mg
Price
$39
Updated
2021/12/16
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MIANSERIN Chemical Properties,Usage,Production

Originator

Tolvin,Organon,W. Germany,1975

Uses

Serotonin receptor antagonist. Antidepressant

Definition

ChEBI: Mianserin is a dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere. It has a role as an antidepressant, a histamine agonist, a sedative, an alpha-adrenergic antagonist, an adrenergic uptake inhibitor, a serotonergic antagonist, a H1-receptor antagonist, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor and a geroprotector.

Manufacturing Process

(A) 25 g of 2-benzylaniline dissolved in 150 ml of benzene are cooled down in an ice bath to 8°C. To this solution are added 15 ml of pyridine and after that a solution of 15 ml of chloroacetyl chloride in 25 ml of benzene, maintaining the temperature of the reaction mixture at 10° to 15°C. After stirring for 1 hour at room temperature 25 ml of water are added and the mixture is shaken for 30 minutes. Next the mixture is sucked off and the benzene layer separated. Then the benzene layer is washed successively with 2 N HCl, a sodium carbonate solution and water. The extract dried on sodium sulfate is evaporated and the residue crystallized together with the crystals obtained already from benzene. Yield 18 g; MP 130° to 133°C.
(B) 40 g of N-chloroacetyl-2-benzylaniline are heated for 2 hours at 120°C together with 50 ml of phosphorus oxychloride and 320 g of polyphosphoric acid. Next the reaction mixture is poured on ice and extracted with benzene. The extract is washed and dried on sodium sulfate and the benzene distilled off. The product obtained (31g) yields after recrystallization 24 g of 6- chloromethyl-morphanthridine of MP 136° to 137°C.
(C) 10 g of 6-chloromethyl-morphanthridine are passed into 150 ml of a solution of methylamine in benzene (10%). After storage of the solution for 20 hours at 0° to 5°C the methylamine hydrochloride formed is sucked off and the filtrate evaporated to dryness. There remains as residue 11 g of crude 6-methylaminomethyl-morphanthridine.
(D) 11 g of crude 6-methylaminomethyl-morphanthridine are dissolved in 50 ml of absolute ether. While cooling in ice 2.7 g of lithium aluminumhydride, dissolved in 100 ml of absolute ether, are added. After boiling for 1 hour and cooling down in ice 11 ml of water are added slowly dropwise while stirring. After stirring for another 30 minutes at room temperature the mixture is sucked off and the filtrate evaporated to obtain 11 g of crude 5,6-dihydro-6- methylaminomethyl-morphanthridine in the form of a light yellow oil.
(E) 10 g of 5,6-dihydro-6-methylaminomethyl-morphanthridine are heated slowly, in 30 minutes, from 100° to 160°C with 7 g of pure diethyloxalate and after that from 160° to 180°C in 45 minutes. After cooling down the reaction mixture is stirred with benzene. The crystals are sucked off and yield after crystallization from dimethylformamide 9 g of 1,2-diketo-3(N)-methyl- 2,3,4,4a-tetrahydro-1H-pyrazino-[1,2-f]-morphanthridine of MP 245° to 247°C.
(F) 9 g of the diketo-pyrazino-morphanthridine compound obtained above are reduced with diborane to give mianserin.

brand name

Athimil;Athymil;Bolvidon;Lantanon;Lerivon;Miansan;Norval;Org gb 94;Tolvin;Tolvon.

Therapeutic Function

Serotonin antagonist, Antihistaminic

World Health Organization (WHO)

Mianserin, a serotonin antagonist with antidepressant and antihistaminic activity, was introduced in 1975 for the treatment of depressive illness. Its use has since been associated with cases of severe blood dyscrasias, particularly in elderly patients, including agranulocytosis, leucopenia and granulocytopenia. Several drug regulatory authorities have reacted by stipulating that blood counts should be monitored regularly during the first few months of treatment and that administration should be discontinued immediately should any signs possibly indicative of dyscrasia develop.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 13, p. 35, 1970 DOI: 10.1021/jm00295a010

MIANSERIN Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from MIANSERIN manufacturers

Dideu Industries Group Limited
Product
Mianserin
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-07-26
Career Henan Chemical Co
Product
MIANSERIN 24219-97-4
Price
US $1.00-2.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg,10kg,100kg
Release date
2019-08-07

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