Home > Compound List > Compound details
61337-67-5 molecular structure
click picture or here to close

5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(19),8(13),9,11,15,17-hexaene

ChemBase ID: 254
Molecular Formular: C17H19N3
Molecular Mass: 265.35286
Monoisotopic Mass: 265.15789762
SMILES and InChIs

SMILES:
N12C(CN(CC1)C)c1c(Cc3c2nccc3)cccc1
Canonical SMILES:
CN1CCN2C(C1)c1ccccc1Cc1c2nccc1
InChI:
InChI=1S/C17H19N3/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20/h2-8,16H,9-12H2,1H3
InChIKey:
RONZAEMNMFQXRA-UHFFFAOYSA-N

Cite this record

CBID:254 http://www.chembase.cn/molecule-254.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(19),8(13),9,11,15,17-hexaene
5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene
5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8(13),9,11,16,18-hexaene
IUPAC Traditional name
5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(19),8(13),9,11,15,17-hexaene
5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene
mirtazapine
Brand Name
Remeron
Remeron Soltab
Zispin
Remergil
Norset
Rexer
Remergon
Mirtabene
Avanza
Mirtazon
Axit
Mirtaz
Promyrtil
Remeron, Avanza, Zispin
Synonyms
Mirtazapina [INN-Spanish]
Mirtazapine [Usan:Ban:Inn]
Mirtazapinum [INN-Latin]
Mirtazepine
Mepirzepine
mirtazapine
Mirtazapine
Remeron
Avanza
Esmirtazapine
1,2,3,4,10,14b-Hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
Mirtazapine
6-Azamianserin
Org 3770
5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene
Org-3770
Zispin
CAS Number
61337-67-5
61337-87-9
85650-52-8
MDL Number
MFCD00865427
PubChem SID
160963717
24724531
46506965
PubChem CID
6451144
4205
CHEBI ID
6950
ATC CODE
N06AX11
CHEMBL
654
Chemspider ID
4060
2342166
DrugBank ID
DB00370
KEGG ID
D00563
D04055
Unique Ingredient Identifier
4685R51V7M
A051Q2099Q
Wikipedia Title
Mirtazapine
Esmirtazapine
Medline Plus
a697009

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.8185004  LogD (pH = 7.4) 3.133914 
Log P 3.2079828  Molar Refractivity 82.6553 cm3
Polarizability 31.225294 Å3 Polar Surface Area 19.37 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.9  LOG S -2.38 
Solubility (Water) 1.10e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO: soluble ~8 mg/mL expand Show data source
Slight expand Show data source
Soluble in methanol and chloroform expand Show data source
Apperance
white powder expand Show data source
White Solid expand Show data source
Melting Point
114-116 °C (237.2-240.8°F) expand Show data source
114-116°C expand Show data source
Boiling Point
432°C (809.6°F) expand Show data source
Density
1.22 g/cm3 expand Show data source
Hydrophobicity(logP)
2.814 expand Show data source
2.9 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
50% expand Show data source
Excretion
Urine (75%)
Feces (15%)
expand Show data source
Half Life
20–40 hours expand Show data source
Metabolism
Liver (CYP1A2, CYP2D6, and CYP3A4) expand Show data source
Liver (CYP2D6) expand Show data source
Protein Bound
85% expand Show data source
Legal Status
Rx-only expand Show data source
Uncontrolled expand Show data source
Pregnancy Category
C expand Show data source
Gene Information
human ... ADRA2A(150), ADRA2C(152), DRD2(1813), DRD3(1814), DRD4(1815), HRH1(3269), HTR1A(3350), HTR2A(3356), HTR2C(3358), HTR7(3363)mouse ... Slc6a2(20538)rat ... Adra1a(29412), Drd1a(24316), Drd2(24318), Htr1a(24473), Htr2a(29595), Htr2c(25187), Slc6a3(24898), Slc6a4(25553) expand Show data source
Purity
≥98% (HPLC) expand Show data source
95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C17H19N3 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC DrugBank DrugBank Selleck Chemicals Selleck Chemicals
Sigma Aldrich - M0443 external link
Biochem/physiol Actions
Mirtazapine is a noradrenergic and specific serotonergic antidepressant (NaSSA). Mirtazapine agonizes selective adrenergic and serotonergic receptors so that both NE release and 5-HT1A mediated serotonergic signaling are increased.
Toronto Research Chemicals - M365000 external link
An α2-Adrenergic blocker; analogue of Mianserin. Antidepressant.
DrugBank - DB00370 external link
Item Information
Drug Groups approved
Description Mirtazapine is an antidepressant introduced by Organon International in 1996 used for the treatment of moderate to severe depression. Mirtazapine has a tetracyclic chemical structure and is classified as a noradrenergic and specific serotonergic antidepressant (NaSSA). It is the only tetracyclic antidepressant that has been approved by the Food and Drug Administration to treat depression. [Wikipedia]
Indication For the treatment of major depressive disorder.
Pharmacology Mirtazapine, an antidepressant of the piperazinoazepine class, is a tetracyclic compound with an anxiolytic effect. Mirtazapine has fewer ADRs than tricyclic antidepressants and is better tolerated. Selective blockade of specific serotonin receptors by mirtazapine likey minimizes side effects typical of other antidepressants.
Toxicity Symptoms of overdose include disorientation, drowsiness, impaired memory, and tachycardia. LD50 is 600-720mg/kg (oral, mice) and 320-490mg/kg (oral, rat) [PMID: 10333982]
Affected Organisms
Humans and other mammals
Biotransformation Mirtazapine is extensively metabolized by demethylation and hydroxylation followed by glucuronide conjugation. Cytochrome P450 2D6 and cytochrome P450 1A2 are involved in formation of the 8-hydroxy metabolite of mirtazapine, and cytochrome P450 3A4 is responsible for the formation of the N-desmethyl and N-oxide metabolites. Several metabolites possess pharmacological activity, but plasma levels are very low.
Absorption Rapid and complete, but, due to first-pass metabolism, absolute bioavailability is 50%.
Half Life 20-40 hours
Protein Binding 85%
Elimination This drug is known to be substantially excreted by the kidney (75%).
References
Gillman PK: A systematic review of the serotonergic effects of mirtazapine in humans: implications for its dual action status. Hum Psychopharmacol. 2006 Mar;21(2):117-25. [Pubmed]
Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. [Pubmed]
Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. [Pubmed]
Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. [Pubmed]
Baldwin DS, Anderson IM, Nutt DJ, Bandelow B, Bond A, Davidson JR, den Boer JA, Fineberg NA, Knapp M, Scott J, Wittchen HU: Evidence-based guidelines for the pharmacological treatment of anxiety disorders: recommendations from the British Association for Psychopharmacology. J Psychopharmacol. 2005 Nov;19(6):567-96. [Pubmed]
[Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S2016 external link
Research Area: Neurological Disease
Biological Activity:
Mirtazapine (Remeron, Avanza) is a potent tetracyclic antidepressant. Mirtazapine (Remeron, Avanza) used primarily in the treatment of depression. It is also sometimes used as a hypnotic, antiemetic, and appetite stimulant, and for the treatment of anxiety, among other indications. In addition, along with its close analogues mianserin and setiptiline, mirtazapine (Remeron, Avanza) is one of the few noradrenergic and specific serotonergic antidepressants (NaSSAs). Additionally, the (S)-(+)-enantiomer of mirtazapine, which is also called esmirtazapine, is currently under development for the treatment of insomnia and menopausal symptoms. Mirtazapine’s primary use is the treatment of major depressive disorder. Mirtazapine (Remeron, Avanza) has been found to be useful in the treatment of many diseases, including generalized anxiety disorder, social anxiety disorder, obsessive-compulsive disorder, panic disorder, post-traumatic stress disorder, seasonal affective disorder, insomnia, nausea and vomiting, diminished appetite and associated weight loss, and itching as well. [1]References on Mirtazapine (Remeron, Avanza)[1] http://en.wikipedia.org/wiki/Mirtazapine, ,

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed
  • •  Pubmed
  • • Gillman PK: A systematic review of the serotonergic effects of mirtazapine in humans: implications for its dual action status. Hum Psychopharmacol. 2006 Mar;21(2):117-25. Pubmed
  • • Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. Pubmed
  • • Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. Pubmed
  • • Baldwin DS, Anderson IM, Nutt DJ, Bandelow B, Bond A, Davidson JR, den Boer JA, Fineberg NA, Knapp M, Scott J, Wittchen HU: Evidence-based guidelines for the pharmacological treatment of anxiety disorders: recommendations from the British Association for Psychopharmacology. J Psychopharmacol. 2005 Nov;19(6):567-96. Pubmed
  • • http://en.wikipedia.org/wiki/Mirtazapine
  • • De Boer, T., et al.: Neuropharmacology, 27, 399 (1988)
  • • Smith, W.T., et al.: Psychopharmacol. Bull., 26, 191 (1990)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle