Nortriptyline

Structural formula
General
Non-proprietary name	Nortriptyline
other names	N -Methyl-3- (10,11-dihydro-5 H -dibenzo [ a , d ] cyclohepten-5-ylidene) propylamine ( IUPAC ) ; Nortriptylinum ( Latin ) ;
Molecular formula	C 19 H 21 N; C 19 H 21 N · HCl (hydrochloride);
Brief description	colorless to yellowish powder (hydrochloride)
External identifiers / databases
EC number	200-788-8
ECHA InfoCard	100,000,717
PubChem	4543
ChemSpider	4384
DrugBank	DB00540
Wikidata	Q61387
Drug information
ATC code	N06 AA10
Drug class	Tricyclic antidepressants
properties
Molar mass	263.38 g · mol -1 ; 299.85 g mol −1 (hydrochloride);
solubility	soluble in water and ethanol (hydrochloride)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Hydrochloride; Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	502 mg kg −1 ( LD 50 , rat , oral ) ; 22 mg kg −1 ( LD 50 , rat , iv ) ; 370 mg kg −1 ( LD 50 , mouse , oral ) ; 17 mg kg −1 ( LD 50 , mouse , iv ) ; 405 mg kg −1 ( LD 50 , rat , oral , hydrochloride) ; 13 mg kg −1 ( LD 50 , rat , iv , hydrochloride) ; 260 mg kg −1 ( LD 50 , mouse , oral , hydrochloride) ; 18.7 mg kg −1 ( LD 50 , mouse , iv , hydrochloride) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nortriptyline is the active metabolite of the tricyclic antidepressant (TCA) amitriptyline . Despite the same mode of action, nortriptyline has less pronounced side effects. That is why it is considered a second generation TZA. Nortriptyline is approved in Germany for the treatment of depression . It is also used in the treatment of enuresis , migraines , chronic pain and ADHD .

Mechanism of action

Nortriptyline works u. a. as FIASMA (functional inhibitor of acid sphingomyelinase ).

unwanted effects

As with other tricyclic antidepressants, the main side effects are anticholinergic effects.

Use in children and adolescents

Nortriptyline is not recommended for the treatment of depression in children and adolescents under 18 years of age.

Use during pregnancy and breastfeeding

There is insufficient experience with the use of nortriptyline during pregnancy. Nortriptyline is the active metabolite of amitriptyline . Amitriptyline showed foetotoxic and teratogenic effects in various animal species after very high doses. The potential risk for humans is unknown. Nortriptyline should not be used during pregnancy, especially in the first and last trimester of pregnancy, unless it is urgently necessary. After administration of higher doses of antidepressants before birth, withdrawal symptoms in the form of cardiac and respiratory disorders, urination and stool evacuation and restlessness were observed in the newborn.

Trade names

Aventyl (USA, CDN), Pamelor (USA), Nortrilen (EU, D), Nortriptyline (D)

Web links

Swiss Medicines Compendium : Nortriptyline Preparations

Wagena EJ, Knipschild PG, Huibers MJ, Wouters EF, van Schayck CP: Efficacy of bupropion and nortriptyline for smoking cessation among people at risk for or with chronic obstructive pulmonary disease . In: Arch. Intern. Med. . 165, No. 19, October 2005, pp. 2286-2292. doi : 10.1001 / archinte.165.19.2286 . PMID 16246996 .

Individual evidence

↑ ^a ^b ^c ^d Datasheet Nortriptyline hydrochloride from Sigma-Aldrich , accessed on October 13, 2018 ( PDF ).
^ ^A ^b ^c ^d ^e ^f ^g ^h A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2000), Thieme-Verlag Stuttgart, ISBN 978-1 -58890-031-9 .
↑ Joseph Biederman, Thomas Spencer, Timothy Wilens: Evidence-based pharmacotherapy for attention-deficit hyperactivity disorder . In: The International Journal of Neuropsychopharmacology . tape 7 , no. 1 , March 2004, ISSN 1461-1457 , p. 77-97 , doi : 10.1017 / S1461145703003973 ( oup.com [accessed May 10, 2020]).
↑ Martin D. Ohlmeier, Mandy Roy: ADHD in adults - a life in extremes: A practical book for therapists and those affected . Kohlhammer Verlag, 2012, ISBN 978-3-17-027410-5 ( google.de [accessed on May 10, 2020]).
↑ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .
↑ Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt. Volume 116, Issue 29 f. (July 22) 2019, pp. 508-517, p. 511.
↑ ^a ^b glenmark.de: Specialist information: Nortriptyline ; Status: April 2018.

[Sigma-1] Datasheet Nortriptyline hydrochloride from Sigma-Aldrich , accessed on October 13, 2018 ( PDF ).

[Kleemann-2] A ^b ^c ^d ^e ^f ^g ^h A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2000), Thieme-Verlag Stuttgart, ISBN 978-1 -58890-031-9 .

[3] Joseph Biederman, Thomas Spencer, Timothy Wilens: Evidence-based pharmacotherapy for attention-deficit hyperactivity disorder . In: The International Journal of Neuropsychopharmacology . tape 7 , no. 1 , March 2004, ISSN 1461-1457 , p. 77-97 , doi : 10.1017 / S1461145703003973 ( oup.com [accessed May 10, 2020]).

[4] Martin D. Ohlmeier, Mandy Roy: ADHD in adults - a life in extremes: A practical book for therapists and those affected . Kohlhammer Verlag, 2012, ISBN 978-3-17-027410-5 ( google.de [accessed on May 10, 2020]).

[pmid18504571-5] Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .

[6] Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt. Volume 116, Issue 29 f. (July 22) 2019, pp. 508-517, p. 511.

[FI-7] rk.de: Specialist information: Nortriptyline ; Status: April 2018.