Home > Compound List > Compound details
10347-81-6 molecular structure
click picture or here to close

methyl(3-{tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9(14),10,12-hexaen-1-yl}propyl)amine

ChemBase ID: 810
Molecular Formular: C20H23N
Molecular Mass: 277.40332
Monoisotopic Mass: 277.18304974
SMILES and InChIs

SMILES:
N(CCCC12CCC(c3c1cccc3)c1c2cccc1)C
Canonical SMILES:
CNCCCC12CCC(c3c1cccc3)c1c2cccc1
InChI:
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
InChIKey:
QSLMDECMDJKHMQ-UHFFFAOYSA-N

Cite this record

CBID:810 http://www.chembase.cn/molecule-810.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl(3-{tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9(14),10,12-hexaen-1-yl}propyl)amine
methyl(3-{tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propyl)amine
methyl(3-{tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2(7),3,5,9(14),10,12-hexaen-1-yl}propyl)amine
IUPAC Traditional name
methyl(3-{tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9(14),10,12-hexaen-1-yl}propyl)amine
maprotiline
Brand Name
Deprilept
Ludiomil
Psymion
Synonyms
N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine Hydrochloride
N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine Hydrochloride
Ba-34276
Deprilept
Ludiomil
Psymion
Maprotiline Hydrochloride
Maprotilina [INN-Spanish]
Maprotiline Hcl
Maprotilinum [INN-Latin]
Maprotylina [Polish]
Maprotiline
CAS Number
10347-81-6
10262-69-8
PubChem SID
46508358
160964273
PubChem CID
4011
ATC CODE
N06AA21
CHEMBL
21731
Chemspider ID
3871
DrugBank ID
DB00934
IUPHAR ligand ID
2402
KEGG ID
D02566
Unique Ingredient Identifier
2U1W68TROF
Wikipedia Title
Maprotiline
Medline Plus
a682158

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
M188000 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.1368963  LogD (pH = 7.4) 1.4832375 
Log P 4.3721046  Molar Refractivity 99.3017 cm3
Polarizability 34.660324 Å3 Polar Surface Area 12.03 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.89  LOG S -6.27 
Solubility (Water) 1.50e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Slightly soluble expand Show data source
Apperance
White Solid expand Show data source
Melting Point
241-243°C expand Show data source
Hydrophobicity(logP)
5.1 expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
oral, intramuscular, intravenous (infusion) expand Show data source
Bioavailability
66 to 70% expand Show data source
Excretion
biliar (30%) and urine (57%) as gluconurides, 3 to 4% as unchanged drug expand Show data source
Half Life
27-58 hours expand Show data source
Metabolism
hepatic expand Show data source
Protein Bound
88% expand Show data source
Legal Status
Rx-only (not a controlled substance) expand Show data source
Pregnancy Category
Sufficient data does not exist. Exert caution. expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00934 external link
Item Information
Drug Groups approved
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.
Indication 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.
Pharmacology Maprotiline is a tetracyclic antidepressant. Although its main therapeutic use is in the treatment of depression, it has also been shown to exert a sedative effect on the anxiety component that often accompanies depression. In one sleep study, it was shown that maprotiline increases the duration of the REM sleep phase in depressed patients, compared to imipramine which reduced the REM sleep phase. Maprotiline is a strong inhibitor of noradrenaline reuptake in the brain and peripheral tissues, however it is worthy to note that it is a weak inhibitor of serotonergic uptake. In addition, it displays strong antihistaminic action (which may explain its sedative effects) as well as weak anticholinergic action. Maprotiline also has lower alpha adrenergic blocking activity than amitriptyline.
Toxicity LD50=~900 mg/kg (Orally in rats); LD50=90 mg/kg (Orally in women); 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.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption Slowly, but completely absorbed from the GI tract following oral administration.
Half Life Average ~ 51 hours (range: 27-58 hours)
Protein Binding 88%
Elimination Approximately 60% of a single orally administered dose is excreted in urine as conjugated metabolites within 21 days; 30% is eliminated in feces.
Distribution Maprotiline and its metabolites may be detected in the lungs, liver, brain, and kidneys; lower concentrations may be found in the adrenal glands, heart and muscle. Maprotiline is readily distributed into breast milk to similar concentrations as those in maternal blood.
External Links
Wikipedia
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Pinder, R.M., et al.: Drugs, 13, 321 (1977)
  • • Suh, SK., et al.: Anal. Profiles Drug Subs., 15, 393 (1977)
  • • Berjukow, S., et al.: J. Biol. Chem., 274, 6154 (1977)
  • • Zahradnikova, A., et al.: J. Pharmacol. Exp Ther., 322, 638 (1977)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle