Triple namine

Structural formula
General
Non-proprietary name	Triple namine
other names	N , N -dimethyl- N ′ - (phenylmethyl) - N ′ -2-pyridinyl-1,2-ethanediamine ( IUPAC ) ; Pyribenzamine;
Molecular formula	C 16 H 21 N 3
Brief description	yellow, amine-like smelling, water-miscible oil (triple namin)
External identifiers / databases
ECHA InfoCard	100.001.910
PubChem	5587
DrugBank	DB00792
Wikidata	Q415203
Drug information
ATC code	R06 AC04 ; D04 AA04 ;
Drug class	Antihistamines
properties
Molar mass	255.36 g · mol -1
density	1.5759–1.5765 g cm −3 (25 ° C)
Melting point	192–193 ° C (tripleennamine hydrochloride) ; 106–110 ° C (triple namine citrate) ;
boiling point	138–142 ° C (13.3 Pa ) (triple namine)
Refractive index	1.576 (25 ° C) ( triple namine )
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: 302-315-319-335
	P: 261-305 + 351 + 338
Toxicological data	23 mg kg −1 ( LD 50 , mouse , iv ) ; 152 mg kg −1 ( LD 50 , mouse , oral ) ; 9 mg kg −1 ( LD 50 , mouse , iv , hydrochloride) ; 97 mg kg −1 ( LD 50 , mouse , oral , hydrochloride) ; 12 mg kg −1 ( LD 50 , rat , iv , hydrochloride) ; 469 mg kg −1 ( LD 50 , rat , oral , hydrochloride) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Tripelennamine (trade name: Azaron ^® ) is a drug of first generation antihistamines . It is used to treat itching after insect bites and allergic skin reactions.

Presentation and extraction

Tripelennamine can be obtained in a two-step synthesis. The first step is a reductive coupling of 2-aminopyridine with benzaldehyde in formic acid . The resulting intermediate product is then reacted with 2-dimethylaminoethyl chloride after deprotonation with sodium amide .

The compound was first synthesized by Carl Djerassi in 1946 .

effect

Tripelennamine belongs to the class of active substances called ethylenediamines and docks with the H ₁ -histamine receptors in the body so that the histamine can no longer act on the cell.

links

Tripelennamin is used in the form of:

Tripelennamine monohydrochloride
Tripelennamine Hydrochloride
Tripelennamine Maleate
Tripelennamine Citrate

Individual evidence

↑ ^a ^b ^c Entry on triple namin. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.
^ ^A ^b The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; Pp. 1672-1673, ISBN 978-0-911910-00-1 .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-194.
↑ ^a ^b Datasheet Tripelennamine hydrochloride from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).
^ ^A ^b ^c ^d ^e ^f ^g A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890 -031-9 .

[RÖMPP_Online-1] Entry on triple namin. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.

[MERCK_Index-2] A ^b The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; Pp. 1672-1673, ISBN 978-0-911910-00-1 .

[CRC90_3_194-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-194.

[Sigma-4] Datasheet Tripelennamine hydrochloride from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).

[Kleemann-5] A ^b ^c ^d ^e ^f ^g A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890 -031-9 .