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Mianserin hydrochloride

Product Name
Mianserin hydrochloride
CAS No.
21535-47-7
Chemical Name
Mianserin hydrochloride
Synonyms
gb94;Tolvin;Tolvon;toluon;Lerivon;athymil;orggb94;Lantanon;bolvidon;Tetramide
CBNumber
CB4389789
Molecular Formula
C18H21ClN2
Formula Weight
300.83
MOL File
21535-47-7.mol
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Mianserin hydrochloride Property

Melting point:
>230oC (dec.)
Flash point:
9℃
storage temp. 
2-8°C
solubility 
H2O: 3.4 mg/mL
form 
Solid
color 
Off-White to Pale Yellow
Water Solubility 
Soluble in water, ethanol, methanol, and dimethylformamide.
Merck 
14,6172
InChIKey
YNPFMWCWRVTGKJ-UHFFFAOYSA-N
CAS DataBase Reference
21535-47-7(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,Xi,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 
HP8780000
HS Code 
2933.59.8000
HazardClass 
6.1(b)
PackingGroup 
III
Toxicity
LD50 in male, female mice (mg/kg): 365, 390 orally; 32.5, 31.0 i.v. (van Riezen)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M2525
Product name
Mianserin hydrochloride
Packaging
100mg
Price
$114
Updated
2024/03/01
Sigma-Aldrich
Product number
M2525
Product name
Mianserin hydrochloride
Packaging
1g
Price
$607
Updated
2024/03/01
Sigma-Aldrich
Product number
M-919
Product name
Mianserin hydrochloride solution
Purity
1.0?mg/mL in methanol (as free base), ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$183
Updated
2022/05/15
TCI Chemical
Product number
M2623
Product name
Mianserin Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$126
Updated
2024/03/01
TCI Chemical
Product number
M2623
Product name
Mianserin Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
200mg
Price
$42
Updated
2024/03/01
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Mianserin hydrochloride Chemical Properties,Usage,Production

Chemical Properties

Off-White Solid

Originator

Tolvin,Organon,W. Germany,1975

Uses

Mianserin hydrochloride is a tetracyclic antidepressant with an EEG and clinical activity profile similar to amitriptyline. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.

Uses

Mianserin hydrochloride is used as an antidepressant, antagonist, inverse agonist at 5-HT2 serotonin receptors, also blocks the H1 histamine receptor and the α2 adrenoceptor.

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.

Therapeutic Function

Serotonin antagonist, Antihistaminic

Biological Activity

Mianserin hydrochloride is a non-selective 5-HT2 receptor antagonist (Ki values are 0.0080 and 0.0081 μM for human 5-HT2A and 5-HT2C receptors expressed in HEK293 cells respectively). Has moderate affinity for 5-HT6. Antidepressant.

Clinical Use

Antidepressant

Drug interactions

Potentially hazardous interactions with other drugs
Alcohol: increased sedative effect.
Antibacterials: avoid with linezolid and tedizolid. Antidepressants: avoid with MAOIs and moclobemide.
Antiepileptics: convulsive threshold possibly lowered; concentration reduced by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone.
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Safinamide: increased risk of hypertension and CNS excitation.

Metabolism

Mianserin is hepatically metabolised via aromatic hydroxylation, N-oxidation and N-demethylation. There are 3 urinary metabolites, (N-desmethyl, 8-hydroxy, and N-oxide derivative) which have been identified. The desmethyl metabolite, which is also active, has similar pharmacokinetic behaviour as the parent compound. Mianserin is excreted in the urine, almost entirely as its metabolites, either free or in conjugated form; 14-28% in the faeces.

storage

Room temperature

Mianserin hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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Mianserin hydrochloride Suppliers

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View Lastest Price from Mianserin hydrochloride manufacturers

Dideu Industries Group Limited
Product
Mianserin hydrochloride 21535-47-7
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 hydrochloride 21535-47-7
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000KGS
Release date
2020-01-02

21535-47-7, Mianserin hydrochlorideRelated Search:

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