Maprotiline

Maprotiline
Clinical data
Trade names	Ludiomil, others
Other names	Maprotiline hydrochloride; Maprotiline methanesulfonate; Ba 34276
AHFS/Drugs.com	Monograph
MedlinePlus	a682158
Routes of; administration	Oral, intramuscular, intravenous
ATC code	N06AA21 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: ℞-only;
Pharmacokinetic data
Bioavailability	66–70%
Protein binding	88%
Metabolism	hepatic
Onset of action	6 hours
Elimination half-life	27–58 hours
Excretion	Urine (57%) and bile (30%) as glucuronides, 3–4% as unchanged drug
Identifiers
	IUPAC name N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine;
CAS Number	10262-69-8 ; 10347-81-6 (hydrochloride); 58902-67-3 (mesylate);
PubChem CID	4011;
IUPHAR/BPS	2402;
DrugBank	DB00934 ;
ChemSpider	23719117 ;
UNII	2U1W68TROF;
KEGG	D02566 ;
ChEMBL	ChEMBL21731 ;
CompTox Dashboard (EPA)	DTXSID7045029 ;
ECHA InfoCard	100.030.532
Chemical and physical data
Formula	C20H23N
Molar mass	277.411 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNCCC[C@]12CC[C@H](c3ccccc31)c1ccccc12;
	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/t15-,20+ ; Key:QSLMDECMDJKHMQ-GSXCWMCISA-N ;
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Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression. It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine. In terms of its chemistry and pharmacology, maprotiline is closely related to such-other secondary-amine TCAs as nortriptyline and protriptyline and has similar effects to them, albeit with more distinct anxiolytic effects. Additionally, whereas protriptyline tends to be somewhat more stimulating and in any case is distinctly more-or-less non-sedating, mild degrees of sedation may be experienced with maprotiline.