Protriptyline

Protriptyline
	Above: molecular structure of protriptyline Below: 3D representation of a protriptyline molecule
Clinical data
Trade names	Vivactyl, others
Other names	Amimethyline; Protriptyline hydrochloride; MK-240
AHFS/Drugs.com	Monograph
MedlinePlus	a604025
Routes of; administration	Oral
ATC code	N06AA11 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	77–93%
Protein binding	92%
Metabolism	Hepatic
Elimination half-life	54–92 hours
Excretion	Urine: 50%; Feces: minor
Identifiers
	IUPAC name 3-(5H-dibenzo[a,d][7]annulen-5-yl)-N-methylpropan-1-amine;
CAS Number	438-60-8 ; 1225-55-4 (hydrochloride);
PubChem CID	4976;
IUPHAR/BPS	7285;
DrugBank	DB00344 ;
ChemSpider	4805 ;
UNII	4NDU154T12;
KEGG	D08447;
ChEBI	CHEBI:8597 ;
ChEMBL	ChEMBL668 ;
CompTox Dashboard (EPA)	DTXSID0023535 ;
ECHA InfoCard	100.006.474
Chemical and physical data
Formula	C19H21N
Molar mass	263.384 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3cc2c(\C=C/c1c(cccc1)C2CCCNC)cc3;
	InChI InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3 ; Key:BWPIARFWQZKAIA-UHFFFAOYSA-N ;
	(verify)

Protriptyline, sold under the brand name Vivactil among others, is a tricyclic antidepressant (TCA), specifically a secondary amine. Uniquely among most of the TCAs, protriptyline tends to be energizing instead of sedating, and is sometimes used for narcolepsy to achieve a wakefulness-promoting effect.

TCAs including protriptyline are also used to reduce the incidence of recurring headaches such as migraine, and for other types of chronic pain.