ContaminantDB: 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:35 UTC

Update Date

2026-04-03 20:26:53 UTC

Accession Number

CHEM002501

Identification

Common Name

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Class

Small Molecule

Description

1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a neurotoxin that causes permanent symptoms of Parkinson's disease by killing certain neurons in the substantia nigra of the brain. While MPTP itself does not have opioid effects, it is related to MPPP, a synthetic opioid drug with effects similar to those of heroin and morphine. MPTP can be accidentally produced during the illicit manufacture of MPPP, and that is how its Parkinson-inducing effects were first discovered. MPTP is used to recreate and study the Parkinson's disease in experimental animal models. (2)

Contaminant Sources

T3DB toxins

Contaminant Type

Amine
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
MPTP	ChEBI
N-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine	MeSH

Chemical Formula

C₁₂H₁₅N

Average Molecular Mass

173.254 g/mol

Monoisotopic Mass

173.120 g/mol

CAS Registry Number

28289-54-5

IUPAC Name

1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Traditional Name

MPTP

SMILES

CN1CCC(=CC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3

InChI Key

PLRACCBDVIHHLZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydropyridines. Hydropyridines are compounds containing a hydrogenated pyridine ring (i.e. containing less than the maximum number of double bonds.).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Hydropyridines

Alternative Parents

Substituents

Benzenoid
Hydropyridine
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

methylpyridines (CHEBI:17963 )
tetrahydropyridine (CHEBI:17963 )
phenylpyridine (CHEBI:17963 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

neurotoxin

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	40-42°C
Boiling Point	85-90 °C (at 0.8 mm Hg)
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.42 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.35	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	8.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	57.47 m³·mol⁻¹	ChemAxon
Polarizability	21.02 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0lk9-1900000000-36d037be627c16feb3bd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-e201fc2a2d42013379aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-99d91f9b67fcd6f34a76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-8900000000-099735f9e4fb38becc8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-d4230bc243608beca34f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-f32b038842a79e5b2695	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05dl-5900000000-3b4830d260c28b17374c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-56283bf2270bbd4df094	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-cbb4be820600db09287e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2900000000-a1f874d4dde6dfbe3b2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-7883e6701106e8531b78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-7ffdbc080be1d9a7b5b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0900000000-396c4310a7b5ec601e1a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

MPTP itself is not toxic, and as a lipophilic compound can cross the blood-brain barrier. Once inside the brain, MPTP is metabolized into the toxic cation 1-methyl-4-phenylpyridinium (MPP+) by the enzyme MAO-B of glial cells. MPP+ primarily kills dopamine-producing neurons in a part of the brain called the pars compacta of the substantia nigra. MPP+ interferes with complex I of the electron transport chain, a component of mitochondrial metabolism, which leads to cell death and causes the buildup of free radicals, toxic molecules that contribute further to cell destruction. (2)

Metabolism

In the brain, MPTP is metabolized into the toxic cation 1-methyl-4-phenylpyridinium (MPP+) by the enzyme MAO-B of glial cells. (2)

Toxicity Values

LD50: 54 mg/kg (Subcutaneous, Mouse) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a neurotoxin that causes permanent symptoms of Parkinson's disease by killing certain neurons in the substantia nigra of the brain. MPTP can be accidentally produced during the illicit manufacture of MPPP, and that is how its Parkinson-inducing effects were first discovered. MPTP is used to recreate and study the Parkinson's disease in experimental animal models.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Because MPTP itself is not directly harmful, toxic effects of acute MPTP poisoning can be mitigated by the administration of monoamine oxidase inhibitors (MAOIs) such as selegiline. MAOIs prevent the metabolism of MPTP to MPP+ by inhibiting the action of MAO-B, minimizing toxicity and preventing neural death. (2)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID