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HomeProduct name list1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

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

Synonym(s):Dopaminergic neurotoxin, MPTP;MPTP hydrochloride;MPTP Hydrochloride - CAS 23007-85-4 - Calbiochem

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

What is 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride?

Chemical properties

White Solid

The Uses of 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride is a dopaminergic neurotoxin that reportedly causes a severe and irreversible Parkinsonian condition in humans and monkeys.

The Uses of 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

MPTP is a neurotoxin used to cause selective destruction of dopaminergic neurons in animal models of parkinsonism. MPTP is metabolized by monoamine oxidase B to produce MPDP+ and MPP+, with MP+ being the active toxic agent. MPP+ induces neurotoxicity primarily by inhibiting complex I of the mitochondrial electron transport chain, resulting in ATP depletion and increased oxidative stress. The key features of different neurotoxic models of Parkinson’s disease, including the MPTP model, have been detailed.[Cayman Chemical]

What are the applications of Application

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine, Hydrochloride is a Dopaminergic neurotoxin precursor of MPP+, widely used in research to study Parkinson′s disease models.

Biochem/physiol Actions

Dopaminergic neurotoxin.

Purification Methods

Purify MPTP by recrystallisation from pKEst ~ Me2CO/isoPrOH. The free base has m 40-42o(from heptane), b 99-100o/1.3mm, 128-132o/12mm, (137-142o/0.8mm), n 25 1.5347. The hydrochloride has m 251-252o(from Me2CO/isoPrOH) [Schmidle & Mansfield J Am Chem Soc 78 425 1956, Defeudis Drug Dev Res 15 1 1988, Beilstein 20 III/IV 3240, 20/7 V 121.]

References

[1] Lun-Yi Zang, Hara P Misra. “Inactivation of acetylcholinesterase by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride.” Molecular and Cellular Biochemistry 254 1–2 (2003): 131–6.
[2] Gregory L. Willis, Alan D. Robertson. “Recovery from experimental Parkinson’s disease in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride treated marmoset with the melatonin analogue ML-23.” Pharmacology Biochemistry and Behavior 80 1 (2005): Pages 9-26.
[3] Atsushi Fujita. “Connexin 30 deficiency attenuates A2 astrocyte responses and induces severe neurodegeneration in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride Parkinson’s disease animal model.” Journal of Neuroinflammation (2018): 227.

Properties of 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

Melting point: 249.0 to 254.0 °C
storage temp.  Inert atmosphere,Room Temperature
solubility  DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form  White solid
color  white to off-white
BRN  3707312
Stability: Light Sensitive
InChI InChI=1S/C12H15N.ClH/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11;/h2-7H,8-10H2,1H3;1H
CAS DataBase Reference 23007-85-4

Safety information for 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H301:Acute toxicity,oral
H370:Specific target organ toxicity, single exposure
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P405:Store locked up.
P501:Dispose of contents/container to..…

Computed Descriptors for 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

InChIKey KOWJANGMTAZWDT-UHFFFAOYSA-N
SMILES C1(=CCN(C)CC1)C1C=CC=CC=1.Cl

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