ContaminantDB: Maprotiline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (17)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:59 UTC

Update Date

2026-03-31 17:59:37 UTC

Accession Number

CHEM002305

Identification

Common Name

Maprotiline

Class

Small Molecule

Description

Maprotiline is a tetracyclic antidepressant with similar pharmacological properties to tricyclic antidepressants (TCAs). Similar to TCAs, maprotiline inhibits neuronal norepinephrine reuptake, possesses some anticholinergic activity, and does not affect monoamine oxidase activity. It differs from TCAs in that it does not appear to block serotonin reuptake. Maprotiline may be used to treat depressive affective disorders, including dysthymic disorder (depressive neurosis) and major depressive disorder. Maprotiline is effective at reducing symptoms of anxiety associated with depression.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

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

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-6090000000-8e89e932860e4ee6b072	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0090000000-7a66545f7844123eba51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0fb9-0090000000-c3b045151955339e59cc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gb9-0590000000-bfeab480527e9e5cb70a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0930000000-406a233a8ad8a3b5d463	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-002f-0920000000-d86cbfa85ef229dfed53	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-0090000000-1a2bf3822fc21e2f8460	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0fb9-0190000000-cf4d09e63ae607c3f690	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gb9-1690000000-32657b0912154e5e6eb5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00kf-1940000000-176ec01fb7ad9b4a11ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0006-1920000000-a721293bed4aff937490	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0006-1910000000-f2d680cb6b1ab57df4bd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0390000000-ae291d01fb28cc38d1de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-002f-0930000000-1eb22c7693a749dd6c69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-0090000000-23fddbd27ba3e5e42a21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-130477a21813cdfe3871	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-002f-0920000000-dfc6b18aea4d0a6e7eb5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0gdl-0790000000-1b7b6a0fb83ed782ad78	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-0090000000-c978fa61248cd5a77295	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-004i-0090000000-d428ee7275d47b035da3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0090000000-7ae10ab99fb7f49ffa27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-1090000000-2d55de2a427af756ca33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3090000000-5aed5f1d5ab04a0db509	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-067ee24bd068071dfb49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1090000000-75ab50229f1a5d9f943a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5a-4090000000-5c180e3dc53a4a98eb97	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f6x-9560000000-f263c228ecd4df5d7e73	Spectrum

Toxicity Profile

Route of Exposure

Slowly, but completely absorbed from the GI tract following oral administration.

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.

Metabolism

Hepatic. Maprotiline is metabolized by N-demethylation, deamination, aliphatic and aromatic hydroxylations and by formation of aromatic methoxy derivatives. It is slowly metabolized primarily to desmethylmaprotiline, a pharmacologically active metabolite. Desmethylmaprotiline may undergo further metabolism to maprotiline-N-oxide. Route of Elimination: Approximately 60% of a single orally administered dose is excreted in urine as conjugated metabolites within 21 days; 30% is eliminated in feces. Half Life: Average ~ 51 hours (range: 27-58 hours)

Toxicity Values

LD50: 900 mg/kg (Oral, Rat) (1) LD50: 90 mg/kg (Oral, Human) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

For treatment of depression, including the depressed phase of bipolar depression, psychotic depression, and involutional melancholia, and may also be helpful in treating certain patients suffering severe depressive neurosis.

Minimum Risk Level

Not Available

Health Effects

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

Concentrations

Not Available

External Links

DrugBank ID

DB00934

HMDB ID

HMDB0015069

FooDB ID

Not Available

Phenol Explorer ID