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MPTP hydrochloride

Dopaminergic neurotoxin,induced reduction in the DOPAC HVA/dopamine (DA) ratio CAS# 23007-85-4

MPTP hydrochloride

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Chemical structure

MPTP hydrochloride

3D structure

Chemical Properties of MPTP hydrochloride

Cas No. 23007-85-4 SDF Download SDF
PubChem ID 161406 Appearance Powder
Formula C12H16ClN M.Wt 209.72
Type of Compound N/A Storage Desiccate at -20°C
Solubility H2O : ≥ 105 mg/mL (500.67 mM)
DMSO : 12 mg/mL (57.22 mM; Need ultrasonic and warming)
*"≥" means soluble, but saturation unknown.
Chemical Name 1-methyl-4-phenyl-3,6-dihydro-2H-pyridine;hydrochloride
SMILES [H+].[Cl-].CN1CCC(=CC1)c2ccccc2
Standard InChIKey KOWJANGMTAZWDT-UHFFFAOYSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of MPTP hydrochloride

DescriptionMPTP (hydrochloride) is a prodrug to the neurotoxin MPP+ which causes permanent symptoms of Parkinson's disease.In Vitro:Pretreatment with 50 mM 4-phenylpyridine, reduces IC50 (concentration for 50% inhibition of twitch amplitude) values of MPTP from 53 to 18 mM and d-tubocurarine from 0.7 to 0.3 mM, respectively, in mouse phrenic nerve-diaphragm[3].In Vivo:The toxic effect of MPTP can be completely abolished in vivo by treatment with a monoamine oxidase inhibitor and potentiated by an inhibitor of catechol-O-methyltransferase[1]. Allopurinol potentiated the MPTP (35 mg/kg)-induced decrease in the DOPAC+HVA/DA ratio and increase in striatal AA oxidation of the rat[2]. Gas1 expressions are significantly elevated in the majority of the reactive astrocytes of the brains with LPS or MPTP insults in animal models[4].

References:
[1]. Langston J W, Irwin I. MPTP Neurotoxicity: An Overview and Characterization of Phases of Toxicity. II. Selective Accumulation of MPP in the Substantia Nigra: A Key to Neurotoxicity (Question). Life Sci., 1985, 36, No. 3, 201-12. [2]. Desole M S, et al. Further investigation of allopurinol effects on MPTP-induced oxidative stress in the striatum and brain stem of the rat. Source:Pharmacol.Biochem.Behav., 1996, 54, No. 2, 377-83. [3]. Hsu K S, et al. Potentiation of MPTP by 4-Phenylpyridine on the Neuromuscular Blockade in Mouse Phrenic Nerve-Diaphragm. Neuropharmacology, 1993, 32, No. 9, 877-83. [4]. Sun XL, et al. Gas1 up-regulation is inducible and contributes to cell apoptosis in reactive astrocytes in the substantia nigra of LPS and MPTP models. J Neuroinflammation. 2016 Jul 8;13(1):180.

Protocol

Animal Administration [4]
For the preparation of the LPS rat model and the MPTP mouse model, the treatments of the animals are performed. Briefly, adult rats receive unilateral injections of LPS (0.5 μL of 10 μg/μL diluted in 0.9% saline) into the medial forebrain bundle (MFB) at the following coordinates, AP-4.2 mm, L 1.5 mm, and V 7.8 mm, and into the contralateral side with the same volume of 0.9% saline. Adult mice are administered intraperitoneal injections of MPTP of 25 mg/kg per day for five continuous days, and the same volume of saline is injected as a control. All the animals are sacrificed at week 1, 2, 3, or 4 after the LPS or MPTP injections. The brain samples are collected for the subsequent immunohistochemistry and western blot experiments.

References:
[1]. Langston J W, Irwin I. MPTP Neurotoxicity: An Overview and Characterization of Phases of Toxicity. II. Selective Accumulation of MPP in the Substantia Nigra: A Key to Neurotoxicity (Question). Life Sci., 1985, 36, No. 3, 201-12. [2]. Desole M S, et al. Further investigation of allopurinol effects on MPTP-induced oxidative stress in the striatum and brain stem of the rat. Source:Pharmacol.Biochem.Behav., 1996, 54, No. 2, 377-83. [3]. Hsu K S, et al. Potentiation of MPTP by 4-Phenylpyridine on the Neuromuscular Blockade in Mouse Phrenic Nerve-Diaphragm. Neuropharmacology, 1993, 32, No. 9, 877-83. [4]. Sun XL, et al. Gas1 up-regulation is inducible and contributes to cell apoptosis in reactive astrocytes in the substantia nigra of LPS and MPTP models. J Neuroinflammation. 2016 Jul 8;13(1):180.

MPTP hydrochloride Dilution Calculator

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MPTP hydrochloride Molarity Calculator

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Preparing Stock Solutions of MPTP hydrochloride

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.7683 mL 23.8413 mL 47.6826 mL 95.3652 mL 119.2066 mL
5 mM 0.9537 mL 4.7683 mL 9.5365 mL 19.073 mL 23.8413 mL
10 mM 0.4768 mL 2.3841 mL 4.7683 mL 9.5365 mL 11.9207 mL
50 mM 0.0954 mL 0.4768 mL 0.9537 mL 1.9073 mL 2.3841 mL
100 mM 0.0477 mL 0.2384 mL 0.4768 mL 0.9537 mL 1.1921 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on MPTP hydrochloride

IC50 Value: 53uM(inhibited the nerve-evoked twitches of phrenic nerve-hemidiaphragm preparations from ICR mice) . MPTP HCl (Sigma-Chem.) induced reduction in the DOPAC HVA/dopamine (DA) ratio and increase in striatal ascorbate (AS) oxidation in rats [1]. in vitro: MPTP inhibited the nerve-evoked twitches of phrenic nerve-hemidiaphragm preparations from ICR mice (20-30 g). PP 50 uM, but not PA 50 uM or TP 50 uM, potentiated the inhibitory effect of MPTP. PP 100 uM itself had an inhibitory action on twitch amplitude. The IC50 values for twitch inhibition by MPTP, TC and PP were 53, 0.7 and 123 uM, respectively. Pretreatment with PP 50 uM reduced the IC50 values of MPTP and TC to 18 and 0.3 uM, respectively[2]. in vivo: MPTP was examined in 12 squirrel monkeys (2 mg/kg every 2 hr for 4 doses) and human addicts self-administering varying doses with varying dosage patterns. In other experiments, 6 squirrel monkeys (0.6-1.0 kg) received MPTP (2 mg/kg every 2 hr for 4 doses). Some animals were pretreated with pargyline. These were killed 1 or 12 hr after the last MPTP dose while the others were killed up to 72 hr after that lase dose. Brain concentrations of MPGP/MPP were determined by GC/MS on a regional basis [3]. Clinical trial: Treatment of Levodopa Induced Dyskinesia in Patients With Parkinson's Disease. Phase II.

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References on MPTP hydrochloride

LC-MS determination of MPTP at sub-ppm level in pethidine hydrochloride.[Pubmed:15862689]

J Pharm Biomed Anal. 2005 Apr 29;37(5):1089-93.

An HPLC-MS with electrospray ionisation method for the determination of MPTP at sub-ppm level in pethidine hydrochloride has been developed and validated. Ionisation is performed by positive-ion electrospray and the quadrupole filter mass spectrometer is operated in the single ion recording mode. Chromatographic separation was achieved in gradient elution using a symmetry C18, 5 microm, 150 mm x 2.1 mm i.d. The mobile phase comprised water containing 0.1% formic acid (v/v) and acetonitrile containing 0.1% formic acid (v/v). The method showed to be linear in the range between 0.2 and 2.2 ng/ml, the estimated LOD was lower than 0.1 ng/ml and the LOQ was lower than 0.2 ng/ml.

Description

MPTP hydrochloride is a brain penetrant dopamine neurotoxin, inducing Parkinson’s Disease. MPTP hydrochloride, a precusor of MPP+, induces apoptosis.

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