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.^[3]

TCAs including protriptyline are also used to reduce the incidence of recurring headaches such as migraine, and for other types of chronic pain.^[4]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c ^d Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 588–. ISBN 978-1-60913-345-0.
^ Schmidt, H. S., Clark, R. W., & Hyman, P. R. (1977). Protriptyline: An effective agent in the treatment of the narcolepsy-cataplexy syndrome and hypersomnia. The American Journal of Psychiatry, 134(2), 183–185. https://doi.org/10.1176/ajp.134.2.183
^ Cohen, G. L. (1997). "Protriptyline, chronic tension-type headaches, and weight loss in women". Headache. 37 (7): 433–436. doi:10.1046/j.1526-4610.1997.3707433.x. ISSN 0017-8748. PMID 9277026.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[LemkeWilliams2012-2] Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 588–. ISBN 978-1-60913-345-0.

[3] Schmidt, H. S., Clark, R. W., & Hyman, P. R. (1977). Protriptyline: An effective agent in the treatment of the narcolepsy-cataplexy syndrome and hypersomnia. The American Journal of Psychiatry, 134(2), 183–185. https://doi.org/10.1176/ajp.134.2.183

[4] Cohen, G. L. (1997). "Protriptyline, chronic tension-type headaches, and weight loss in women". Headache. 37 (7): 433–436. doi:10.1046/j.1526-4610.1997.3707433.x. ISSN 0017-8748. PMID 9277026.

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