Maprotiline (CED0006021)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:59 UTC

Update Date

2026-05-14 16:53:17 UTC

SynCED ID

CED0006021

Secondary Accession Numbers

CHEM002305
T3D2934

Identification

Common Name

Maprotiline

Class

Small Molecule

Description

Maprotiline is an exogenous organic compound with the formula C20H23N and an average molecular weight of 277.40 g/mol. It exists as a solid at room temperature. Maprotiline belongs to the anthracenes, a class of benzenoids within the organic compounds. This compound is found in antidepressants, radio transmission systems, antennas, electrically stimulated smoking devices, tobacco smoke filters, other smoking requisites, non-electric simulated smoking devices, and perfumes within detergents and soaps. The recorded exposure route for this substance is oral. Maprotiline targets 20 proteins, including the sodium-dependent noradrenaline transporter (SLC6A2), the histamine H1 receptor (HRH1), the alpha-1A adrenergic receptor (ADRA1A), and amine oxidase [flavin-containing] B (MAOB). It also acts as an antagonist of muscarinic acetylcholine receptors M1, M2, M3, and M4, as well as 12 other proteins. Maprotiline exerts its antidepressant action by inhibiting the presynaptic uptake of catecholamines, which increases their concentration at the synaptic clefts of the brain. In single doses, its effect on the EEG is characterized by an increase in alpha-wave amplitude and density, alongside a reduction in alpha-wave frequency. Similar to other tricyclic antidepressants, maprotiline lowers the convulsive threshold. It may be used to treat major depressive disorder and dysthymic disorder (depressive neurosis), and it is effective at reducing symptoms of anxiety associated with depression. Pharmacologically, it inhibits neuronal norepinephrine reuptake and possesses some anticholinergic activity, but it does not affect monoamine oxidase activity or appear to block serotonin reuptake.

Contaminant Type

Adrenergic Uptake Inhibitor
Amine
Antidepressant
Antidepressant, Second-Generation
Antidepressive Agent
Antidepressive Agent, Second-Generation
Drug
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
BA-34276	HMDB
Declimed brand OF maprotiline hydrochloride	HMDB
Deprilept	HMDB
Dibencycladine	HMDB
Holsten brand OF maprotiline hydrochloride	HMDB
Maprotilin-teva	HMDB
Maprotilin-neuraxpharm	HMDB
Mesylate, maprotiline	HMDB
Novopharm brand OF maprotiline hydrochloride	HMDB
Psymion	HMDB
Neuraxpharm brand OF maprotiline hydrochloride	HMDB
Ratiopharm brand OF maprotiline hydrochloride	HMDB
Maprotilin neuraxpharm	HMDB
Maprotilin-ratiopharm	HMDB
Maprotiline mesylate	HMDB
Novo-maprotiline	HMDB
Teva brand OF maprotiline hydrochloride	HMDB
Maprotilin von CT	HMDB
Dolorgiet brand OF maprotiline hydrochloride	HMDB
Hexal brand OF maprotiline mesylate	HMDB
Hydrochloride, maprotiline	HMDB
Ludiomil	HMDB
Lundbeck brand OF maprotiline hydrochloride	HMDB
Maprotilin	HMDB
Maprotilin holsten	HMDB
Maprotiline hydrochloride	HMDB
Mirpan	HMDB
N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine	HMDB
CT-Arzneimittel brand OF maprotiline hydrochloride	HMDB
Maprolu	HMDB
Maprotilin teva	HMDB
Maprotilin ratiopharm	HMDB
Novartis brand OF maprotiline hydrochloride	HMDB
Novo maprotiline	HMDB

Chemical Formula

C₂₀H₂₃N

Average Molecular Mass

277.403 g/mol

Monoisotopic Mass

277.183 g/mol

CAS Registry Number

10262-69-8

IUPAC Name

methyl(3-{tetracyclo[6.6.2.0²,⁷.0⁹,¹⁴]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propyl)amine

Traditional Name

maprotiline

SMILES

CNCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

InChI Identifier

InChI=1S/C20H23N/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20/h2-5,7-10,15,21H,6,11-14H2,1H3

InChI Key

QSLMDECMDJKHMQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Tetralin
Aralkylamine
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthracenes (CHEBI:6690 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	93°C
Boiling Point	Not Available
Solubility	Slightly soluble

Predicted Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	4.89	ALOGPS
logP	4.37	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	10.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.3 m³·mol⁻¹	ChemAxon
Polarizability	33.57 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	splash10-0a4l-6090000000-8e89e932860e4ee6b072	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0090000000-7a66545f7844123eba51	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fb9-0090000000-c3b045151955339e59cc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0590000000-bfeab480527e9e5cb70a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0930000000-406a233a8ad8a3b5d463	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002f-0920000000-d86cbfa85ef229dfed53	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0090000000-1a2bf3822fc21e2f8460	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fb9-0190000000-cf4d09e63ae607c3f690	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-1690000000-32657b0912154e5e6eb5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-1940000000-176ec01fb7ad9b4a11ca	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-1920000000-a721293bed4aff937490	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-1910000000-f2d680cb6b1ab57df4bd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0390000000-ae291d01fb28cc38d1de	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002f-0930000000-1eb22c7693a749dd6c69	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fb9-0090000000-23fddbd27ba3e5e42a21	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0090000000-130477a21813cdfe3871	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002f-0920000000-dfc6b18aea4d0a6e7eb5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gdl-0790000000-1b7b6a0fb83ed782ad78	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fb9-0090000000-c978fa61248cd5a77295	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0090000000-d428ee7275d47b035da3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fb9-0190000000-f20c0729c7cecfafb4dd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0090000000-7a66545f7844123eba51	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0590000000-15a310c0d762caff25ff	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-1940000000-7d3be91d56a2e4eec356	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-1690000000-8bad06f6b8677a77392f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0930000000-1eb22c7693a749dd6c69	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-1920000000-0788a33070790d10cccf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-1910000000-4ef49ea885e3afb68794	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0590000000-9f89f8882e9996496e26	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0930000000-407ec2145d4e27750df8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-3930000000-2aa508b9b3fffc15e19a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-3920000000-3a150f64268f0f0f12a6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-3920000000-ff233e20d41dc5887e24	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-1390000000-1ae80e5b2919257f0220	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-066u-3960000000-f289177cda7f5c54b51b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0090000000-f3acc778e8b19c2c20bc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002f-0920000000-706b6b2a2bdd0327289a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004j-0090000000-7ae10ab99fb7f49ffa27	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002b-1090000000-2d55de2a427af756ca33	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-3090000000-5aed5f1d5ab04a0db509	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0090000000-067ee24bd068071dfb49	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-1090000000-75ab50229f1a5d9f943a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a5a-4090000000-5c180e3dc53a4a98eb97	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0090000000-4e2261d857b5f6d2110a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0090000000-261042fc11ae45536540	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-0290000000-38465239fc33d45f55d1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0090000000-c524df0015f139e69d14	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0090000000-c524df0015f139e69d14	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-70f1252de774a3933396	Not Available	View Spectrum
MS	MS Spectrum	splash10-0f6x-9560000000-f263c228ecd4df5d7e73	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
900.0 mg/kg	Rat	LD50	Oral	experimental	Not Available	1
90.0 mg/kg	Human	LD50	Oral	experimental	Not Available	1
630.0 Log mg/kg [350:1100]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Maprotiline exerts its antidepressant action by inhibition of presynaptic uptake of catecholamines, thereby increasing their concentration at the synaptic clefts of the brain. In single doses, the effect of maprotiline on the EEG revealed a rise in the alpha-wave density, a reduction of the alpha-wave frequency and an increase in the alpha-wave amplitude. However, as with other tricyclic antidepressants, maprotiline lowers the convulsive threshold. Maprotiline acts as an antagonist at central presynaptic α₂-adrenergic inhibitory autoreceptors and hetero-receptors, an action that is postulated to result in an increase in central noradrenergic and serotonergic activity. Maprotiline is also a moderate peripheral α₁ adrenergic antagonist, which may explain the occasional orthostatic hypotension reported in association with its use. Maprotiline also inhibits the amine transporter, delaying the reuptake of noradrenaline and norepinephrine. Lastly, maprotiline is a strong inhibitor of the histamine H₁ receptor, which explains its sedative actions.

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Signs of overdose include motor unrest, muscular twitching and rigidity, tremor, ataxia, convulsions, hyperpyrexia, vertigo, mydriasis, vomiting, cyanosis, hypotension, shock, tachycardia, cardiac arrhythmias, impaired cardiac conduction, respiratory depression, and disturbances of consciousness up to deep coma.

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	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
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	PubChem
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	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
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	PubChem
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	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
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	PubChem
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	PubChem
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	PubChem
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	PubChem
CEDs000613	Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
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	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
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	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
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	PubChem
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	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
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	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
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	PubChem
CEDs000727	Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.	Paper, pulp & fiber products	PubChem
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	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

3 pathwaysPathway Source: PathBank

Maprotiline Action Pathway

Maprotiline Drug Metabolism Action Pathway

Maprotiline H1 Antihistamine Neurological Sleep Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	Prediction Confidence Score 0.428 Applicability Domain 1.0 Statistical Significance 0.0032 Supporting Reference Compounds 451 E-value 24.6782
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	Prediction Confidence Score 0.417 Applicability Domain 1.0 Statistical Significance 0.0043 Supporting Reference Compounds 506 E-value 33.6309
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.415 Applicability Domain 1.0 Statistical Significance 0.0152 Supporting Reference Compounds 955 E-value 118.331
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Predicted (SEA)	Prediction Confidence Score 0.403 Applicability Domain 1.0 Statistical Significance 0.0051 Supporting Reference Compounds 294 E-value 39.5474
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.398 Applicability Domain 1.0 Statistical Significance 0.0047 Supporting Reference Compounds 208 E-value 36.9005
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	Prediction Confidence Score 0.397 Applicability Domain 1.0 Statistical Significance 0.0017 Supporting Reference Compounds 266 E-value 13.6236
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.396 Applicability Domain 1.0 Statistical Significance 0.0131 Supporting Reference Compounds 823 E-value 102.372
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.395 Applicability Domain 1.0 Statistical Significance 0.0062 Supporting Reference Compounds 487 E-value 48.4222
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	Prediction Confidence Score 0.394 Applicability Domain 1.0 Statistical Significance 0.0051 Supporting Reference Compounds 386 E-value 39.9366
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.394 Applicability Domain 1.0 Statistical Significance 0.0096 Supporting Reference Compounds 536 E-value 74.9688
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.387 Applicability Domain 1.0 Statistical Significance 0.0046 Supporting Reference Compounds 340 E-value 35.9663
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.387 Applicability Domain 1.0 Statistical Significance 0.0101 Supporting Reference Compounds 686 E-value 79.017
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	Prediction Confidence Score 0.386 Applicability Domain 1.0 Statistical Significance 0.0111 Supporting Reference Compounds 507 E-value 86.4905
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	Prediction Confidence Score 0.386 Applicability Domain 1.0 Statistical Significance 0.0043 Supporting Reference Compounds 385 E-value 33.6309
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.386 Applicability Domain 1.0 Statistical Significance 0.0248 Supporting Reference Compounds 1103 E-value 193.377
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	Prediction Confidence Score 0.385 Applicability Domain 1.0 Statistical Significance 0.0032 Supporting Reference Compounds 373 E-value 25.2231
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	Prediction Confidence Score 0.385 Applicability Domain 1.0 Statistical Significance 0.0026 Supporting Reference Compounds 297 E-value 20.0851
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.383 Applicability Domain 1.0 Statistical Significance 0.0027 Supporting Reference Compounds 130 E-value 21.3307
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.378 Applicability Domain 1.0 Statistical Significance 0.0201 Supporting Reference Compounds 861 E-value 156.477
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.378 Applicability Domain 1.0 Statistical Significance 0.0315 Supporting Reference Compounds 1538 E-value 244.992
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	Prediction Confidence Score 0.375 Applicability Domain 1.0 Statistical Significance 0.0037 Supporting Reference Compounds 310 E-value 28.9599
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	Prediction Confidence Score 0.374 Applicability Domain 1.0 Statistical Significance 0.01 Supporting Reference Compounds 425 E-value 78.2385
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	Prediction Confidence Score 0.371 Applicability Domain 1.0 Statistical Significance 0.0064 Supporting Reference Compounds 258 E-value 49.59
Click to view 3D structure	Histamine H2 receptor	P25021	Humans	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 1.0 Statistical Significance 0.0054 Supporting Reference Compounds 256 E-value 42.1943
Click to view 3D structure	Voltage-dependent N-type calcium channel subunit alpha-1B	Q00975	Humans	Predicted (SEA)	Prediction Confidence Score 0.347 Applicability Domain 1.0 Statistical Significance 1.40e-04 Supporting Reference Compounds 25 E-value 1.08989
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Known	Maprotiline exerts its antidepressant action by inhibition of presynaptic uptake of catecholamines, thereby increasing their concentration at the synaptic clefts of the brain. In single doses, the effect of maprotiline on the EEG revealed a rise in the alpha-wave density, a reduction of the alpha-wave frequency and an increase in the alpha-wave amplitude. However, as with other tricyclic antidepressants, maprotiline lowers the convulsive threshold. Maprotiline acts as an antagonist at central presynaptic α2 adrenergic inhibitory autoreceptors and hetero-receptors, an action that is postulated to result in an increase in central noradrenergic and serotonergic activity. Maprotiline is also a moderate peripheral α1 adrenergic antagonist, which may explain the occasional orthostatic hypotension reported in association with its use. Maprotiline also inhibits the amine transporter, delaying the reuptake of noradrenaline and norepinephrine. Lastly, maprotiline is a strong inhibitor of the histamine H1 receptor, which explains its sedative actions.
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Known	Maprotiline exerts its antidepressant action by inhibition of presynaptic uptake of catecholamines, thereby increasing their concentration at the synaptic clefts of the brain. In single doses, the effect of maprotiline on the EEG revealed a rise in the alpha-wave density, a reduction of the alpha-wave frequency and an increase in the alpha-wave amplitude. However, as with other tricyclic antidepressants, maprotiline lowers the convulsive threshold. Maprotiline acts as an antagonist at central presynaptic α2 adrenergic inhibitory autoreceptors and hetero-receptors, an action that is postulated to result in an increase in central noradrenergic and serotonergic activity. Maprotiline is also a moderate peripheral α1 adrenergic antagonist, which may explain the occasional orthostatic hypotension reported in association with its use. Maprotiline also inhibits the amine transporter, delaying the reuptake of noradrenaline and norepinephrine. Lastly, maprotiline is a strong inhibitor of the histamine H1 receptor, which explains its sedative actions.
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Known	Not Available
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Known	Maprotiline exerts its antidepressant action by inhibition of presynaptic uptake of catecholamines, thereby increasing their concentration at the synaptic clefts of the brain. In single doses, the effect of maprotiline on the EEG revealed a rise in the alpha-wave density, a reduction of the alpha-wave frequency and an increase in the alpha-wave amplitude. However, as with other tricyclic antidepressants, maprotiline lowers the convulsive threshold. Maprotiline acts as an antagonist at central presynaptic α2 adrenergic inhibitory autoreceptors and hetero-receptors, an action that is postulated to result in an increase in central noradrenergic and serotonergic activity. Maprotiline is also a moderate peripheral α1 adrenergic antagonist, which may explain the occasional orthostatic hypotension reported in association with its use. Maprotiline also inhibits the amine transporter, delaying the reuptake of noradrenaline and norepinephrine. Lastly, maprotiline is a strong inhibitor of the histamine H1 receptor, which explains its sedative actions.
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Known	Not Available
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Known	Not Available
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Known	Not Available
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Known	Not Available
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Known	Maprotiline exerts its antidepressant action by inhibition of presynaptic uptake of catecholamines, thereby increasing their concentration at the synaptic clefts of the brain. In single doses, the effect of maprotiline on the EEG revealed a rise in the alpha-wave density, a reduction of the alpha-wave frequency and an increase in the alpha-wave amplitude. However, as with other tricyclic antidepressants, maprotiline lowers the convulsive threshold. Maprotiline acts as an antagonist at central presynaptic α2 adrenergic inhibitory autoreceptors and hetero-receptors, an action that is postulated to result in an increase in central noradrenergic and serotonergic activity. Maprotiline is also a moderate peripheral α1 adrenergic antagonist, which may explain the occasional orthostatic hypotension reported in association with its use. Maprotiline also inhibits the amine transporter, delaying the reuptake of noradrenaline and norepinephrine. Lastly, maprotiline is a strong inhibitor of the histamine H1 receptor, which explains its sedative actions.

Concentrations

Not Available

External Links

DrugBank ID

DB00934

HMDB ID

HMDB0015069

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

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Link

General References

Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [PubMed: 18048412]
Drugs.com - http://www.drugs.com/cons/Maprotiline.html

Maprotiline (CED0006021)

Structure for CHEM002305: Maprotiline

Structure