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

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

InChIKey

KOWJANGMTAZWDT-UHFFFAOYSA-N

SMILES

C1(=CCN(C)CC1)C1C=CC=CC=1.Cl

CAS DataBase Reference

23007-85-4

Safety Information

Hazard Codes 

T

Risk Statements 

25-39/23/24/25-36/37/38

Safety Statements 

45-39-26

RIDADR 

2811

WGK Germany 

3

RTECS 

UT8358950

HS Code 

2933.39.9200

HazardClass 

6.1(b)

PackingGroup 

III

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Uses

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.

Uses

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]

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.

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride(23007-85-4)Related Product Information

• 4-Pyridineacetic acid hydrochloride
• Topotecan hydrochloride
• 3-Pyridylacetic acid hydrochloride
• 2,6-Lutidine
• Thiophanate-methyl
• Pyridine hydrochloride
• 2,4,6-Collidine
• 2-Pyridylacetic acid hydrochloride
• PHENYL VALERATE
• Bensulfuron methyl
• 4-Methylpyridine
• Kresoxim-methyl
• 4-Phenylpyridine
• Chlorodimethylphenylsilane
• Azamethiphos
• Methylparaben
• Methyl
• Methyl bromide