Norharman

Structural formula
General
Surname	Norharman
other names	β-carboline; 9H-pyrido [3,4- b ] indole; Carbazoline; 2,9-diazafluorene;
Molecular formula	C 11 H 8 N 2
Brief description	crystalline solid
External identifiers / databases
EC number	205-959-0
ECHA InfoCard	100.005.418
PubChem	64961
Wikidata	Q414226
properties
Molar mass	168.19 g mol −1
Physical state	firmly
Melting point	198-200 ° C
solubility	soluble in water; slightly soluble in most organic solvents;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Norharman (β-carboline) is a chemical compound from the beta-carboline group . It represents the basic structure of the Rauwolfia alkaloids .

Occurrence

Pink Catharanthe ( Catharanthus roseus ).

Like Harman, Norharman occurs in some plant species ( Catharanthus roseus , Lolium perenne , Festuca species). Some types of bacteria synthesize it from tryptophan through several intermediate stages . In low concentrations (5 to 30 ppb) it occurs through pyrolysis from amino acids (mainly tryptophan) in grilled meat, fish and in cigarette smoke. It has also been detected in espresso.

properties

Norharman is a crystalline solid. It fluoresces blue in dilute acidic solution.

use

Norharman is used as a matrix for the analysis of cyclodextrins and sulfated oligosaccharides in combination with DHB as a co-matrix. It acts as an inhibitor of indolamine 2,3-dioxygenase (IDO).

safety instructions

In the Ames test , Norharman shows a comutagenic effect. Its neurotoxic potential was pointed out. It increases the benzo [α] pyrene-induced mutagenicity and acts as an enzyme inhibitor.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g data sheet Norharmane, crystalline from Sigma-Aldrich , accessed on May 3, 2017 ( PDF ).
↑ ^a ^b ^c ^d Entry on β-carboline. In: Römpp Online . Georg Thieme Verlag, accessed on May 3, 2017.
↑ Spektrum.de: Rauwolfiaalkaloide - Lexikon der Chemie , accessed on May 3, 2017.
↑ Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke . CRC Press, 2012, ISBN 978-1-4200-7884-8 , pp. 1750 ( limited preview in Google Book search).
^ John Buckingham, Keith H. Baggaley, Andrew D. Roberts, Laszlo F. Szabo: Dictionary of Alkaloids, Second Edition with CD-ROM . CRC Press, 2010, ISBN 978-1-4200-7770-4 , pp. 366 ( limited preview in Google Book search).
↑ ^a ^b Burkhard Fugmann: RÖMPP Lexikon Naturstoffe, 1st edition, 1997 . Georg Thieme Verlag, 2014, ISBN 3-13-179541-7 , p. 2008 ( limited preview in Google Book Search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet Norharmane, crystalline from Sigma-Aldrich , accessed on May 3, 2017 ( PDF ).

[RömppOnline-2] Entry on β-carboline. In: Römpp Online . Georg Thieme Verlag, accessed on May 3, 2017.

[spektrum.de-3] Spektrum.de: Rauwolfiaalkaloide - Lexikon der Chemie , accessed on May 3, 2017.

[Alan_Rodgman,_Thomas_A._Perfetti-4] Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke . CRC Press, 2012, ISBN 978-1-4200-7884-8 , pp. 1750 ( limited preview in Google Book search).

[John_Buckingham,_Keith_H._Baggaley,_Andrew_D._Roberts,_Laszlo_F._Szabo-5] John Buckingham, Keith H. Baggaley, Andrew D. Roberts, Laszlo F. Szabo: Dictionary of Alkaloids, Second Edition with CD-ROM . CRC Press, 2010, ISBN 978-1-4200-7770-4 , pp. 366 ( limited preview in Google Book search).

[Burkhard_Fugmann-6] Burkhard Fugmann: RÖMPP Lexikon Naturstoffe, 1st edition, 1997 . Georg Thieme Verlag, 2014, ISBN 3-13-179541-7 , p. 2008 ( limited preview in Google Book Search).