Hygrin

Structural formula
General
Surname	Hygrin
other names	(+) - hygrin; ( R ) -1- (1-Methylpyrrolidin-2-yl) -propan-2-one;
Molecular formula	C 8 H 15 NO
External identifiers / databases
EC number	207-822-0
ECHA InfoCard	100.007.112
PubChem	440933
Wikidata	Q2376404
properties
Molar mass	141.21 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hygrin , more precisely ( R ) - (+) - hygrin, is a pyrrolidine alkaloid and also belongs to the group of ketones . It was isolated - together with Cuscohygrin - for the first time by Carl Liebermann in 1889 .

Occurrence

Hygrin is an alkaloid of the coca plant , the main alkaloid of which is cocaine. The roots of the poison berry ( Nicandra physaloides L.) contain around 0.5% by mass of hygrin.

Coca leaves
The poison berry ( Nicardra physaloides ) contains hygrin as the main alkaloid.

Biochemical significance

( R ) - (+) - Hygrin serves nature as a preliminary product for the formation of tropane alkaloids , ( S ) - (-) - Hygrin is not suitable for this.

properties

( R ) - (+) - Hygrin racemizes relatively easily to ( RS ) - (±) -hygrin.

synthesis

Two syntheses for ( R ) - (+) - hygrin are described. In the method of Hyeung-geun Park et al. are a phase transfer catalysis and is a ring-key reactions. In another method, a derivative of the amino acid ( R ) - proline is used as a starting material for the production of ( R ) - (+) - hygrin.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ ^A ^b Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich 2006, p. 249, ISBN 978-3-906390-29-1 .
↑ ^a ^b B.A. McGaw, JG Wooley, Phytochemistry 17 (1978), 257.
^ Jeong-Hee Lee, Byeong-Seon Jeong, Jin-Mo Ku, Sang-sup Jew, Hyeung-geun Park: Total Synthesis of (+) - Hygrine via Asymmetric Phase-transfer Catalytic Alkylation , J. Org. Chem. 71 ( 2006), 6690-6692.
↑ Enzo B. Arévalo-García, Juan Carlos Q. Colmenares: A short synthesis of (+) - hygrine , Tetrahedron Letters 49 (2008), 3995-3996; doi : 10.1016 / j.tetlet.2008.04.098 .

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Gossauer-2] A ^b Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich 2006, p. 249, ISBN 978-3-906390-29-1 .

[McGaw-3] B.A. McGaw, JG Wooley, Phytochemistry 17 (1978), 257.

[Park-4] Jeong-Hee Lee, Byeong-Seon Jeong, Jin-Mo Ku, Sang-sup Jew, Hyeung-geun Park: Total Synthesis of (+) - Hygrine via Asymmetric Phase-transfer Catalytic Alkylation , J. Org. Chem. 71 ( 2006), 6690-6692.

[Enzo-5] Enzo B. Arévalo-García, Juan Carlos Q. Colmenares: A short synthesis of (+) - hygrine , Tetrahedron Letters 49 (2008), 3995-3996; doi : 10.1016 / j.tetlet.2008.04.098 .