Mirtazapine (CED0002665)

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:43 UTC

Update Date

2026-05-14 16:36:49 UTC

SynCED ID

CED0002665

Secondary Accession Numbers

CHEM002182
T3D2767

Identification

Common Name

Mirtazapine

Class

Small Molecule

Description

Mirtazapine is an exogenous solid with the chemical formula C17H19N3 and an average molecular weight of 265.35 g/mol. Mirtazapine belongs to the piperazinoazepines, a class of organoheterocyclic compounds within the organic compounds. It is used as an antidepressant and an anxiolytic drug. Biologically, it functions as an alpha-adrenergic antagonist, a serotonergic antagonist, a histamine antagonist, and an H1-receptor antagonist. The compound targets 24 proteins, including the Alpha-2A adrenergic receptor (ADRA2A), Alpha-2C adrenergic receptor (ADRA2C), 5-hydroxytryptamine receptor 2A (HTR2A), 5-hydroxytryptamine receptor 2C (HTR2C), 5-hydroxytryptamine receptor 3A (HTR3A), 5-hydroxytryptamine receptor 7 (HTR7), D(2) dopamine receptor (DRD2), and D(3) dopamine receptor (DRD3). Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, which inhibits negative feedback to the presynaptic nerve and causes an increase in NE release. The blockade of heteroreceptors, specifically alpha(2)-receptors in serotonergic neurons, enhances the release of 5-HT. This increases interactions between 5-HT and 5-HT1 receptors, contributing to the anxiolytic effects of the compound. Additionally, mirtazapine acts as a potent antagonist at 5-HT and a weak antagonist at 5-HT1 receptors. Exposure to mirtazapine occurs via the oral route. It is found in 14 recorded sources, including antidepressants within healthcare, pharmaceuticals, and veterinary products. Other sources include floors in building and construction; food preservation and the preparation of malt in food processing; cigar cigarettes, tobacco smoke filters, non electric simulated smoking devices, and other smoking requisites in household cleaning and consumer products; as well as antennas, discharge lamps, electrically stimulated smoking devices, radio transmission systems, and relays in electrical and electronic equipment.

Contaminant Type

Adrenergic alpha-Antagonist
Amine
Antidepressive Agent, Tricyclic
Drug
Food Toxin
Histamine H1 Antagonist
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2,3,4,10,14b-Hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)benzazepine	ChEBI
Mirtazapina	ChEBI
Mirtazapinum	ChEBI
Remeron	Kegg
Reflex	Kegg
Mepirzepine	HMDB
Mirtazepine	HMDB
Celltech brand OF mirtazapine	MeSH, HMDB
Norset	MeSH, HMDB
Organon brand OF mirtazapine	MeSH, HMDB
Rexer	MeSH, HMDB
(N-Methyl-11C)mirtazapine	MeSH, HMDB
Remergil	MeSH, HMDB
6-Azamianserin	MeSH, HMDB
Mundogen brand OF mirtazapine	MeSH, HMDB
Zispin	MeSH, HMDB
Esmirtazapine	MeSH, HMDB
(S)-Mirtazapine	MeSH, HMDB
6 Azamianserin	MeSH, HMDB

Chemical Formula

C₁₇H₁₉N₃

Average Molecular Mass

265.353 g/mol

Monoisotopic Mass

265.158 g/mol

CAS Registry Number

61337-67-5

IUPAC Name

5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene

Traditional Name

mirtazapine

SMILES

CN1CCN2C(C1)C1=CC=CC=C1CC1=C2N=CC=C1

InChI Identifier

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

InChI Key

RONZAEMNMFQXRA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperazinoazepines. Piperazinoazepines are compounds containing a piperazinoazepine skeleton, which consists of an azepine ring fused to a piperazine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperazinoazepines

Sub Class

Not Available

Direct Parent

Piperazinoazepines

Alternative Parents

Substituents

Benzazepine
Piperazino-azepine
Dialkylarylamine
Azepine
N-methylpiperazine
N-alkylpiperazine
Aralkylamine
Imidolactam
Benzenoid
Pyridine
Piperazine
1,4-diazinane
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Amine
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzazepine (CHEBI:6950 )
tetracyclic antidepressant (CHEBI:6950 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	114-116°C
Boiling Point	Not Available
Solubility	Slight

Predicted Properties

Property	Value	Source
Water Solubility	1.1 g/L	ALOGPS
logP	2.9	ALOGPS
logP	3.21	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	6.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	19.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.66 m³·mol⁻¹	ChemAxon
Polarizability	30.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0kmr-0190000000-a83848620967f6019b9d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0920000000-0a76314cf99840d246ad	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-1920000000-27fff664f04384263f02	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014j-0790000000-5653705decf2e797e122	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0090000000-57eb768d0827fa54b248	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014j-0490000000-4baae8cca5ab43f65dd9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0910000000-c22ff3266fd0a936312d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-ba0af76733c8ba5925ce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-1b44d823d26f0e0bcd4d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0090000000-3582965e74f282e6bdea	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-3290000000-d8839a66bb5976dbb5fd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006t-5930000000-9d1fc48d559a70f6a0e1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-2910000000-7c8bdce5145b9fd2fda0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-1900000000-05e225af5ed24498466e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-1900000000-f4e13abbfa0358ad282c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-2900000000-0a101b135d8e91d9b9a2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014l-2900000000-6c01bee517524e647dc2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014u-3900000000-7b5b5e6493206d8c9a67	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014j-0890000000-37665999329d651a1038	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0920000000-0a76314cf99840d246ad	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-1920000000-27fff664f04384263f02	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014j-0790000000-5653705decf2e797e122	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-2910000000-63ecec66eeef916c6ccf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0090000000-7d63abc3646b01e9ca0b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-0900000000-63232fade3bde30c6818	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-678be0a9bfb1ed536c71	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-2950000000-2464dfff7291a6b8cdd9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-188428ac1ead3f2201d6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-1900000000-52931454dd3d205ff69a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0910000000-ebe33f0df102bc70c88d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014j-0590000000-cedd20423f87d71c2ba0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0090000000-20f759a0c51a5d69477b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006t-5930000000-d0dad0928324882b6cce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-2910000000-7e32a7766e258af4e9c2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014j-0490000000-702664f3de6e3ce3c327	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0940000000-4827fbe25df141946d68	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-1900000000-8f8b08f7faf72898db6a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-0900000000-7d763778c0b22d9de30e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-3290000000-fce2cec1b68b7a62e31c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0090000000-04dc9387d4431aa56b82	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-6e5cbbcea259afd6ae2b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014j-0590000000-abc7164ceb33c0c42732	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-7317c8e3c74e54196aa7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-850d707320b5c89dca38	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0597-8940000000-134bd5046c73cedf41ee	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0090000000-32137ba60af471e694c7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0090000000-9965f37f1c8e24b8492c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0920000000-48a76a8fca592616a5e9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0090000000-eb9a3591bd2583334616	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0090000000-ce4a476a1796e9be54e2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06yc-1690000000-f770e28caaab1eb4c886	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-7e22bb674a6dd638c95f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-8d29f0e6203d6b7d7af0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kk-1690000000-3b2eb319278a65aeaaeb	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
600.0 mg/kg [600:720]	mice	LD50	oral	experimental	Not Available	9
320.0 mg/kg [320:490]	rat	LD50	oral	experimental	Not Available	9
618.0 Log mg/kg [350:1100]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT₁ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT₁ receptors and as a potent antagonist at 5-HT₂ (particularly subtypes 2A and 2C) and 5-HT₃ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Symptoms of overdose include disorientation, drowsiness, impaired memory, and tachycardia.

Treatment

Treatment should consist of those general measures employed in the management of overdose with any drug effective in the treatment of major depressive disorder. Ensure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large-bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion, or in symptomatic patients. Activated charcoal should be administered. There is no experience with the use of forced diuresis, dialysis, hemoperfusion or exchange transfusion in the treatment of mirtazapine overdosage. No specific antidotes for mirtazapine are known. (8)

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000377	Antidepressants?Antidepressants, a class of synthetic chemicals designed to alleviate symptoms of depression and anxiety, can enter the environment through various pathways, leading to contamination of water systems.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000497	Floors?Floors in built environments can be a significant source of synthetic chemical contamination due to the materials and finishes used in their construction.	Building & Construction	Not Available
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	Not Available
CEDs000514	Discharge Lamps?Discharge lamps, including fluorescent and high-intensity discharge (HID) lamps, are commonly used for lighting applications due to their energy efficiency and brightness.	Electrical & Electronic Equipment	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	Not Available
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	Not Available
CEDs000531	Relays?Relays are electromechanical switches used to control circuits and manage electrical loads.	Electrical & Electronic Equipment	Not Available
CEDs000538	Thin Magnetic Films?Thin magnetic films are layers of magnetic material ranging from a few nanometers to several micrometers in thickness, commonly used in applications such as magnetic sensors, data storage devices, and electronic components.	Electrical & Electronic Equipment	Not Available
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	Not Available
CEDs000547	Preparation Of Malt?Malt preparation involves the germination and drying of cereal grains, primarily barley, to produce malt for brewing and food products.	Food, food processing & cookware	Not Available
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	Not Available
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	Not Available
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	Not Available
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	Not Available
CEDs000579	Manufacture Of Iron Or Steel?The manufacture of iron or steel involves various processes, including smelting, refining, and alloying, which can result in the release of synthetic chemicals and contaminants.	Industrial manufacturing & chemical processing	Not Available
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	Not Available
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	Not Available
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	Not Available
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	Not Available
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	Not Available
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	Not Available
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	Not Available
CEDs000643	Headwear?Headwear made from synthetic materials often incorporates chemicals used in the manufacturing and finishing processes, such as dyes, flame retardants, and water repellents.	Textiles, leather & furnishings	Not Available
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	Not Available
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	Not Available
CEDs000686	Clay Wares?Clay wares are ceramic products made from natural clay, often utilized in various construction applications such as tiles, bricks, and sanitary ware.	Building & Construction	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	Not Available
CEDs000718	Ink Receptacles?Ink receptacles, commonly utilized in printing processes, can be a source of synthetic chemical contamination due to the solvents, pigments, and additives contained within the inks.	Paper, pulp & fiber products	Not Available
CEDs000734	Coating Compositions?Coating compositions, which include paints, sealants, and varnishes, are formulated with a variety of synthetic chemicals such as solvents, resins, pigments, and additives.	Building & Construction	Not Available
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	Not Available
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	Not Available
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	Not Available

Pathways

8 pathwaysPathway Source: PathBank

Mirtazapine H1-Antihistamine Action

Mirtazapine Serotonin Antagonist Action Pathway

Mirtazapine Drug Metabolism Action Pathway

Mirtazapine H1 Antihistamine Neurological Sleep Action Pathway

Mirtazapine Predicted Metabolism Pathway

Mirtazapine H1 Antihistamine Smooth Muscle Relaxation Action Pathway

Mirtazapine H1-Antihistamine Blood Vessel Constriction Action Pathway

Mirtazapine H1-Antihistamine Immune Response Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P08909	Rat	Predicted (SEA)	Prediction Confidence Score 0.635 Applicability Domain 1.0 Statistical Significance 2.20e-04 Supporting Reference Compounds 185 E-value 1.71268
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.635 Applicability Domain 1.0 Statistical Significance 3.70e-04 Supporting Reference Compounds 380 E-value 2.88042
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	Prediction Confidence Score 0.623 Applicability Domain 1.0 Statistical Significance 0.0012 Supporting Reference Compounds 528 E-value 9.57545
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.618 Applicability Domain 1.0 Statistical Significance 0.0014 Supporting Reference Compounds 861 E-value 11.2881
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	Prediction Confidence Score 0.618 Applicability Domain 1.0 Statistical Significance 8.40e-04 Supporting Reference Compounds 524 E-value 6.53933
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.618 Applicability Domain 1.0 Statistical Significance 0.0016 Supporting Reference Compounds 953 E-value 12.1445
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.617 Applicability Domain 1.0 Statistical Significance 6.10e-04 Supporting Reference Compounds 297 E-value 4.7488
Click to view 3D structure	Norepinephrine transporter	Q9WTR4	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.603 Applicability Domain 1.0 Statistical Significance 2.40e-04 Supporting Reference Compounds 112 E-value 1.86838
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.542 Applicability Domain 1.0 Statistical Significance 0.0029 Supporting Reference Compounds 541 E-value 22.4206
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	Prediction Confidence Score 0.518 Applicability Domain 1.0 Statistical Significance 0.0016 Supporting Reference Compounds 507 E-value 12.6894
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.518 Applicability Domain 1.0 Statistical Significance 0.0026 Supporting Reference Compounds 823 E-value 20.63
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.518 Applicability Domain 1.0 Statistical Significance 0.0038 Supporting Reference Compounds 955 E-value 29.5827
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.517 Applicability Domain 1.0 Statistical Significance 0.0065 Supporting Reference Compounds 1103 E-value 50.602
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.516 Applicability Domain 1.0 Statistical Significance 0.0012 Supporting Reference Compounds 487 E-value 9.49761
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	Prediction Confidence Score 0.516 Applicability Domain 1.0 Statistical Significance 0.0019 Supporting Reference Compounds 376 E-value 14.7914
Click to view 3D structure	D(1A) dopamine receptor	P18901	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.509 Applicability Domain 1.0 Statistical Significance 0.0014 Supporting Reference Compounds 206 E-value 11.2881
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	Prediction Confidence Score 0.509 Applicability Domain 1.0 Statistical Significance 8.90e-04 Supporting Reference Compounds 386 E-value 6.92858
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.503 Applicability Domain 1.0 Statistical Significance 0.0028 Supporting Reference Compounds 565 E-value 22.187
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.491 Applicability Domain 1.0 Statistical Significance 9.40e-04 Supporting Reference Compounds 340 E-value 7.31783
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.473 Applicability Domain 1.0 Statistical Significance 0.0019 Supporting Reference Compounds 203 E-value 14.5578
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	Prediction Confidence Score 0.428 Applicability Domain 0.651 Statistical Significance 0.0033 Supporting Reference Compounds 365 E-value 25.5345
Click to view 3D structure	5-hydroxytryptamine receptor 3A	P46098	Humans	Predicted (SEA)	Prediction Confidence Score 0.405 Applicability Domain 1.0 Statistical Significance 0.0022 Supporting Reference Compounds 228 E-value 17.2047
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.399 Applicability Domain 0.651 Statistical Significance 0.0032 Supporting Reference Compounds 154 E-value 24.9118
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	Prediction Confidence Score 0.37 Applicability Domain 0.651 Statistical Significance 0.0058 Supporting Reference Compounds 385 E-value 45.5418
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.36 Applicability Domain 0.651 Statistical Significance 0.0154 Supporting Reference Compounds 536 E-value 119.888
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Known	Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT₁ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT₁ receptors and as a potent antagonist at 5-HT₂ (particularly subtypes 2A and 2C) and 5-HT₃ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Known	Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT₁ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT₁ receptors and as a potent antagonist at 5-HT₂ (particularly subtypes 2A and 2C) and 5-HT₃ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Known	Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT₁ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT₁ receptors and as a potent antagonist at 5-HT₂ (particularly subtypes 2A and 2C) and 5-HT₃ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.
Click to view 3D structure	5-hydroxytryptamine receptor 3A	P46098	Humans	Known	Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT₁ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT₁ receptors and as a potent antagonist at 5-HT₂ (particularly subtypes 2A and 2C) and 5-HT₃ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Known	Not Available
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Known	Not Available
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Known	Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT₁ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT₁ receptors and as a potent antagonist at 5-HT₂ (particularly subtypes 2A and 2C) and 5-HT₃ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Known	Not Available
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Known	Not Available
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Known	Not Available
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Known	Not Available
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Known	Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT₁ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT₁ receptors and as a potent antagonist at 5-HT₂ (particularly subtypes 2A and 2C) and 5-HT₃ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Known	Not Available
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Known	Not Available
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Known	Not Available
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Known	Not Available
Click to view 3D structure	Beta-1 adrenergic receptor	P08588	Humans	Known	Not Available
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Known	Not Available
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Known	Not Available
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Known	Mirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT₁ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT₁ receptors and as a potent antagonist at 5-HT₂ (particularly subtypes 2A and 2C) and 5-HT₃ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.

Concentrations

Not Available

External Links

DrugBank ID

DB00370

HMDB ID

HMDB0251951

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Mirtazapine

Chemspider ID

4060

ChEBI ID

6950

PubChem Compound ID

Not Available

Kegg Compound ID

C07570

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Leonid Metzger, “Methods for the preparation of mirtazapine intermediates.” U.S. Patent US20020165238, issued November 07, 2002.

MSDS

Link

General 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: 16342227]
Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. [PubMed: 9090576]
Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. [PubMed: 11757992]
Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. [PubMed: 10446735]
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: 16272179]
Fawcett J, Barkin RL: Review of the results from clinical studies on the efficacy, safety and tolerability of mirtazapine for the treatment of patients with major depression. J Affect Disord. 1998 Dec;51(3):267-85. [PubMed: 10333982]
Drugs.com - http://www.drugs.com/cons/Mirtazapine.html
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/
WikiTox description of Mirtazapine - http://curriculum.toxicology.wikispaces.net/2.1.11.9.2.4.2+Mirtazapine
Pubmed - http://www.ncbi.nlm.nih.gov/pubmed/10333982

Mirtazapine (CED0002665)

Structure for CHEM002182: Mirtazapine

Structure