1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride
Synonym(s):Dopaminergic neurotoxin, MPTP;MPTP hydrochloride;MPTP Hydrochloride - CAS 23007-85-4 - Calbiochem
- CAS NO.:23007-85-4
- Empirical Formula: C12H16ClN
- Molecular Weight: 209.72
- MDL number: MFCD00012790
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-05-24 13:24:25
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) |
Skull and Crossbones Acute Toxicity GHS06 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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