Mirtazapine

Base Information

• Chemical Name: Mirtazapine
• CAS No.: 61337-67-5
• Molecular Formula: C₁₇H₁₉N₃
• Molecular Weight: 265.358
• Hs Code.: 2933990090
• Mol file: 61337-67-5.mol

Synonyms:Mirtabene;2-Methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine;

Chemical Property of Mirtazapine

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 114-116 °C
• Boiling Point: 432.4 °C at 760 mmHg
• PKA: pKa 7.1(47% MeOH in H2O,t =25,I=0.15(KCl)) (Uncertain)
• Flash Point: 215.3 °C
• PSA: 19.37000
• Density: 1.22 g/cm³
• LogP: 2.48180
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~8 mg/mL, soluble

Purity/Quality:

99%, ^*data from raw suppliers

Mirtazapine solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 22-24/25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Description: Mirtazapine is an antidepressant launched in the Netherlands. Mirtazapine is a potent antagonist of presynaptic α2 receptors as well as a moderately potent 5-HT antagonist. Studies suggested that blockade of α2-adrenoceptors, but not inhibition of noradrenaline uptake, is involved in the mechanism of the antidepressant action of mirtazapine. Mirtazapine has demonstrated efficacy in various studies in depressed patients, being equal or more potent than mianserin, amitriptyline, etc. and exhibiting less anticholinergic and gastrointestinal side effects and low cardiovascular toxicity. In addition to its antidepressant effects, studies in animals indicated that mirtazapine has anxiolytic andor hypnotic activity.
• Uses: antidepressant;antagonist at the H1, 5-HT2A, 5-HT2C, 5-HT3, and a2-adrenergic receptors, in that order of potency
• Therapeutic Function: Antidepressant, Antihistaminic, Antidiuretic
• Biological Functions: Mirtazapine (Remeron) enhances both serotonergic and noradrenergic neurotransmission. By blocking presynaptic α2-adrenoceptors, mirtazapine causes release of norepinephrine. Indirectly, through noradrenergic modulation of serotonin systems, mirtazapine also causes increased release of serotonin. It is an antagonist at the 5-HT2A, 5HT2C, 5-HT3, and histamine receptors but has minimal affinity for muscarinic or α1-receptors. Mirtazapine does not inhibit neuronal reuptake of serotonin or norepinephrine.Weight gain and sedation are common side effects; sedation necessitates dosing at bedtime. Mirtazapine does not have significant effects on cytochrome P450 isoenzymes.
• Clinical Use: Mirtazapine is a piperazinodibenzoazepine antidepressant that is an isostere of the antidepressant mianserin. A seemingly simple isosteric replacement of an aromatic methine group (CH) in mianserin with a nitrogen to give a pyridine ring (mirtazapine) has profound effects on the physicochemical properties, pharmacokinetics, mechanisms of action, and antidepressant activities. Profound differences between receptor affinity and transporter affinity, pharmacokinetics, regioselectivity in the formation of metabolites, and toxicity are observed for mianserin and mirtazapine and their antidepressant mechanisms of action. The pyridine ring increases the polarity of the molecule and decreases the measured partition coefficient and the basicity. Mianserin is a potent inhibitor of NET , whereas mirtazapine has negligible effects on the inhibition of NET (pKi = 7.1 vs. 5.8 respectively).

Technology Process of Mirtazapine

There total 54 articles about Mirtazapine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(14bS)-1,2,3,4,10,14b-Hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepin-10-ol (1071546-36-5) → (+)-Mirtazapine (61337-87-9,61337-67-5,61364-37-2)

Guidance literature:

(14bS)-1,2,3,4,10,14b-Hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepin-10-ol; With aluminum (III) chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 50 ℃; for 18.25h;

With sodium hydroxide; water; sodium tartrate; In tetrahydrofuran; at 0 ℃; pH=14; Product distribution / selectivity;

Reference yield: 95.0%

2-(4-methyl-2-phenylpiperazin-1-yl)-pyridine-3-methanol (61337-89-1) → Mirtazapine (85650-52-8,61337-67-5,61364-37-2)

Guidance literature:

With sulfuric acid;

Reference yield: 89.0%

2-(4-methyl-2-phenyl-1-piperazinyl)-3-pyridinecarboxylic acid (61338-13-4) → Mirtazapine (85650-52-8,61337-67-5,61364-37-2)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene; at 10 - 40 ℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere;

upstream raw materials:

2-(4-methyl-2-phenylpiperazin-1-yl)-pyridine-3-methanol

2-chloro-3-pyridinecarbonitrile

1-methyl-3-phenylpiperazine

2-(4-methyl-2-phenyl-1-piperazinyl)-3-pyridinecarboxylic acid

Downstream raw materials:

1,2,3,4,10,14b-hexahydro-8-bromo-2-methyl-pyrazino<2,1-a>pyrido<2,3-c><2>benzazepine

(-)-Mirtazapine

S-mirtazapine malonate

Refernces

• 1、 -. "METHOD FOR PRODUCING PHENYLPIPERAZINE PYRIDINE METHYL ACETATE". Paragraph 0043-0048. . Retrieved 2020/03/04.
• 2、 Zhu,Li, Shuang,Zhou, Li,Li, Qing,Guo, Xingjie. "Simultaneous enantioselective determination of seven psychoactive drugs enantiomers in multi-specie animal tissues with chiral liquid chromatography coupled with tandem mass spectrometry". . . Retrieved 2019/07/31.