1-methyl-4-phenylpyridinium

Structural formula
General
Surname	1-methyl-4-phenylpyridinium
other names	1-methyl-4-phenylpyridin-1-ium; MPP + ; Cyperquat ( trade name );
Molecular formula	C 12 H 12 N +
Brief description	yellow solid (iodide)
External identifiers / databases
PubChem	39484
Wikidata	Q161645
properties
Molar mass	170.25 g mol −1 ; 297.13 g mol −1 ;
Physical state	solid (iodide)
solubility	soluble in water (> 10 mg / ml, iodide)
safety instructions
GHS labeling of hazardous substances Iodide; danger
H and P phrases	H: 301-311-315-319-331-335
	P: 261-280-301-305 + 351 + 338-311
Toxicological data	27.5 mg kg −1 ( LD 50 , mouse , unknown )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1-Methyl-4-phenylpyridinium (MPP ⁺ ) is a quaternary ammonium compound from the family of bipyridine herbicides.

The neurotoxin MPTP is oxidized to MPP ⁺ in the brain by the enzyme MAO-B . It causes Parkinson's in primates by killing certain dopamine- producing neurons in the substantia nigra .

use

The chloride salt of MPP ⁺ was marketed as a herbicide under the trade name Cyperquat and is structurally related to the herbicide paraquat . In the European Union and in Switzerland, 1-methyl-4-phenylpyridinium is not approved as a crop protection agent.

Individual evidence

↑ ^a ^b ^c ^d data sheet MPP ⁺ iodide ≥98% (HPLC), solid from Sigma-Aldrich , accessed on May 21, 2012 ( PDF ).
↑ Entry on 1-methyl-4-phenylpyridinium in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Salach, JI, Singer TP, Castagnoli N. Jr, Trevor A. (1984): Oxidation of the neurotoxic amine 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) by monoamine oxidases A and B and suicide inactivation of the enzymes by MPTP. In: Biochem. Biophys. Res. Commun. 125 (2): pp. 831-835; PMID 6335034 .
↑ Singer, TP, Salach JI, Castagnoli N. Jr, Trevor A. (1986): Interactions of the neurotoxic amine 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine with monoamine oxidases. In: Biochem. J. 235 (3): pp. 785-789; PMID 3489461 ; PMC 1146756 (free full text).
^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 20, 2016.

[Sigma-1] ta sheet MPP ⁺ iodide ≥98% (HPLC), solid from Sigma-Aldrich , accessed on May 21, 2012 ( PDF ).

[ChemIDplus-2] Entry on 1-methyl-4-phenylpyridinium in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[3] Salach, JI, Singer TP, Castagnoli N. Jr, Trevor A. (1984): Oxidation of the neurotoxic amine 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) by monoamine oxidases A and B and suicide inactivation of the enzymes by MPTP. In: Biochem. Biophys. Res. Commun. 125 (2): pp. 831-835; PMID 6335034 .

[4] Singer, TP, Salach JI, Castagnoli N. Jr, Trevor A. (1986): Interactions of the neurotoxic amine 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine with monoamine oxidases. In: Biochem. J. 235 (3): pp. 785-789; PMID 3489461 ; PMC 1146756 (free full text).

[5] Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 20, 2016.