774-52-7

Usage

Type

Synthetic compound.

Use

Induce Parkinson's disease-like symptoms in animal models for scientific research.

Toxicity

Potent neurotoxin.

Effects on the brain

Causes irreversible damage to the dopaminergic system.

Symptoms

Tremors, rigidity, and bradykinesia (slowness of movement).

Metabolism

Metabolized in the body to form MPP+.

Active toxic agent

MPP+ disrupts mitochondria and leads to cell death.

Significance

Discovery of MPTP's ability to induce Parkinson's-like symptoms has advanced our understanding of the disease and contributed to the development of new treatments and therapies.

InChI:InChI=1/C12H17N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-6,12H,7-10H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 10272-49-8 4-phenylpiperidine hydrochloride 
• 771-99-3 4-phenylpiperidine 
• 74-88-4 methyl iodide 
• 4972-68-3 1-methyl-4-phenyl-piperidin-4-ol 
• 3627-62-1 1-methyl-4-phenyl-piperidine-4-carbonitrile 
• 3627-48-3 pethidinic acid 
• 28289-54-5 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine 
• 51-75-2 nitrogen mustard 
• 10469-27-9 α,α-bis(2-hydroxyethyl)phenylacetonitrile 
• 100119-73-1 1,5-dichloro-3-cyano-3-phenylpentane 
• 70179-05-4 2-phenyl-4-vinyloxy-2-(2-vinyloxy-ethyl)-butyronitrile 
• 546-68-9 titanium(IV) isopropylate 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 121233-57-6 1,1'-dimethyl-4,4'-diphenyl-1,1'-butanediyl-bis-piperidinium; dibromide 
• 121812-58-6 1,1'-dimethyl-4,4'-diphenyl-1,1'-pentanediyl-bis-piperidinium; dibromide 
• 884-00-4 1-ethyl-1-methyl-4-phenyl-piperidinium; iodide 
• 141642-80-0 4-Phenyl-piperidine-1-carbodithioic acid cyclohexyl ester 
• 113237-07-3 4-Phenyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 141642-79-7 4-Phenyl-piperidine-1-carbodithioic acid propyl ester 
• 111313-24-7 4-Phenyl-piperidine-1-carbodithioic acid methyl ester 
• 771-99-3 4-phenylpiperidine 
• 454482-12-3 4-(1-methyl-4-piperidyl)-phenylamine 
• 85684-13-5 4-(4-ethylphenyl)-1-methyl-piperidine 
• 114980-40-4 N-methyl-4-phenyl-2-piperidinone 
• 1196482-62-8 C₁₂H₁₅NO₂ 
• 354813-48-2 methyl 4-(1-methylpiperidin-4-yl)benzoate 
• 1071756-46-1 C₁₃H₁₉NO 

Relevant academic research and scientific papers

Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach

A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Kn?lker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).

Pyrazolo [3,4 - the b] pyridine and [...] composition preparation method and use of (by machine translation)

The present invention provides a pyrazolo [3,4 - the b] pyridine and [...] compound of preparation and use, in particular, the present invention provides a following formula (I) compounds are shown, wherein the definition of each group as described in the specification. The compounds of the invention has excellent tyrosine kinase inhibiting activity, so can be used for preparing a series of treating diseases associated with the tyrosine kinase activity of the drug. (by machine translation)

NOVEL INHIBITORS

The invention relates to novel pyrrolidine derivatives of formula (I): wherein R1, R2 and R3 are as defined herein, as inhibitors of glutaminyl cyclase (QC, EC 2.3.2.5). QC catalyzes the intramolecular cyclization of N-terminal glutamine residues into pyroglutamic acid (5-oxo-prolyl, pGlu*) under liberation of ammonia and the intramolecular cyclization of N-terminal glutamate residues into pyroglutamic acid under liberation of water.

Interactions of 1-methyl-3-phenylpyrrolidine and 3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexane with monoamine oxidase B

The parkinsonian inducing agent 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and its corresponding five-membered ring analogue 1-methyl-3-phenyl-3-pyrroline are cyclic tertiary allylamines and good substrates of monoamine oxidase B (MAO-B). The MAO-B catalyzed 2-electron α-carbon oxidation of this class of substrates appears to be dependent on the presence of the allylic π-bond since the corresponding saturated piperidinyl analogue of MPTP is reported not to be an MAO-B substrate. The only saturated cyclic tertiary amine known to act as an MAO-B substrate is the 3,4-cyclopropyl analogue of MPTP, 3-methyl-6-phenyl-3-azabicyclo[4.1.0]heptane. As part of our ongoing studies we have examined the MAO-B substrate properties of the corresponding pyrrolidinyl analogue, 1-methyl-3-phenylpyrrolidine, and the 3,4-cyclopropyl analogue, 3-methyl-1-phenyl-3-azabicyclo[3.1.0]hexane. The results document that both the pyrrolidinyl analogue [Km = 234 μM; Vmax = 8.37 nmol/(min-mg mitochondrial protein)] and the 3,4-cyclopropyl analogue [Km = 148 μM; Vmax = 16.9 nmol/(min-mg mitochondrial protein)] are substrates of baboon liver mitochondrial MAO-B. We also have compared the neurotoxic potential of these compounds in the C57BL/6 mouse. The results led us to conclude that these compounds are not MPTP-type neurotoxins.

The prediction of1H chemical shifts in amines: A semiempirical and ab initio investigation

Twenty one conformationally fixed amines and their N,N-dimethyl derivatives were obtained commercially or synthesized. These included cis and trans 4-o-butyl cyclohexylamine, 2-exo and 2-endo norbornylamine, 2-adamantylamine, 4-phenylpiperidine, 1-napthyl

SUBSTITUTED ARYL-AMINE DERIVATIVES AND METHODS OF USE

The present invention provides classes of compounds, including-their pharmaceutically acceptable derivatives, useful for treating angiogenesis and related diseases such as cancer. Formula I and II wherein R is a 9- or 10-membered heterocyclyl ring selected from 7-isoquinolinyl,..2-methyl-3-oxo-2,3-dihydroindazol-6-yl, [1,6]-naphthydrin-3-yl, [1,7]-naphthydrin-2-yl, 1-oxo-2,3-dihydrobenzofuran-4-yl, 3-oxo-2,3-dihydrobenzofuran-5-yl, dihydro-benzodioxinyl, 6-quinazolinyl, 2-amino-6-quinazolinyl, 4-methylamino-6-quinazolinyl, 2,4-diamino-6 quinazolinyl, 3-oxo-3,4-dihydro-1,4-benzoxazin-6-yl, 2,2-difluoro-l;3-benzodioxol-5-yl and 2,2,3,3 tetrafluoro-2,3-dihydro-l,4-benzodioxin-6-yl, each of which is optionally substituted with one or more substituents selected from halo, haloakyl, C1-6 alkyl, C2-8 alkenyl, C2-8 alkynyl, N-dimethylamino-C1-6-alkyl, N-dimethylamino-C1-6-alkoxy, amino, alkyl-carbonylamino, morpholino-sulfonyl, amino-sulfonyl, oxazolyl, pyrrolyl,4 morpholinyl, carboxyl, cyano, and acetyl; wherein R1 in formula I is selected from unsubstituted or substituted phenyl, 5-6 membered heteroaryl, 9-10 membered bicyclic heterocyclyl and 11-14 membered tricyclic heterocyclyl, and R1 in formula II is selected from specific bicyclic heterocycles.

QUINOLINE- AND ISOQUINOLINE-BASED COMPOUNDS EXHIBITING ATP-UTILIZING ENZYME INHIBITORY ACTIVITY, AND COMPOSITIONS, AND USES THEREOF

Quinoline- and isoquinoline-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, methods of using compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions comprising compounds exhibiting ATP-utilizing enzyme inhibitory activity, are disclosed.

Substituted alkylamine derivatives and methods of use

Selected amines are effective for prophylaxis and treatment of diseases, such as angiogenesis mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

Substituted amine derivatives and methods of use

Selected amines are effective for prophylaxis and treatment of diseases, such as angiogenesis mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

Structure-affinity relationships of a unique nicotinic ligand: N1-dimethyl-N4-phenylpiperazinium iodide (DMPP)

DMPP is a well-known nicotinic agonist that does not fit any proposed pharmacophore for nicotinic binding and represents a unique ligand among the hundreds of nicotinic agonists studied in the past decades. A systematic modulation of the chemical structure of DMPP, aimed to establish its structure-affinity relationships, is reported. The research has allowed to identify molecules such as 11c, 13c, 14c, and 28c, with affinities for α4β2 receptors in the low nanomolar range, some 2 orders of magnitude lower than the lead compound. The agonistic properties of the most interesting compounds have been assessed by measuring their analgesic activity on mice (hot-plate test). Another result of the research was the identification of DMPP analogues, such as 3a (Ki = 90 nM) and 14b (Ki = 180 nM), that maintain affinity for the central nicotinic receptor when the ammonium function is changed into an aminic one and are therefore possible leads for drug development in neurodegenerative diseases.