ChemicalBook > CAS DataBase List > 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

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

Product Name
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride
CAS No.
23007-85-4
Chemical Name
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride
Synonyms
MPTP;MPTP HCl;MPTP HYDROCHLORIDE;0MPTP hydrochloride;Methyl Hydrochloride;23007-85-4/28289-54-5;NSC 139654 Hydrochloride;Pethidine EP Impurity B HCl;MPTP hydrochloride, 10 mM in DMSO;1-METHYL-4-PHENYL-1 2 3 6-TETRAHYDROPYR&
CBNumber
CB0133791
Molecular Formula
C12H16ClN
Formula Weight
209.72
MOL File
23007-85-4.mol
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1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride Property

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
Water Solubility 
water: 100mg/mL
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
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H370Causes damage to organs

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M0896
Product name
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride
Purity
powder
Packaging
10mg
Price
$135
Updated
2025/07/31
Sigma-Aldrich
Product number
M0896
Product name
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride
Purity
powder
Packaging
100mg
Price
$405
Updated
2025/07/31
Sigma-Aldrich
Product number
5.06382
Product name
MPTP Hydrochloride - CAS 23007-85-4 - Calbiochem
Packaging
10mg
Price
$187
Updated
2025/07/31
TCI Chemical
Product number
M2690
Product name
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine Hydrochloride
Purity
>98.0%(HPLC)
Packaging
25mg
Price
$82
Updated
2025/07/31
TCI Chemical
Product number
M2690
Product name
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine Hydrochloride
Purity
>98.0%(HPLC)
Packaging
100mg
Price
$241
Updated
2025/07/31
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1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride Chemical Properties,Usage,Production

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.

in vivo

MPTP hydrochloride can be used in animal modeling to create Parkinson's disease models. MPTP replicates naturally occurring neurodegeneration and is useful for studying dopaminergic neuronal degeneration, mitochondrial dysfunction, and neuroinflammation. After injection, MPTP is rapidly metabolized to MPP+, which has a serum half-life of approximately 6 days in sheep.

Induction of Parkinsonism model[4][5][6][7]
Background
MPTP is free to cross the blood-brain barrier and enter the brain, where it is metabolized by monoamine oxidase B (MAO-B) in astrocytes into MPP+, its active & toxic form. MPP+ is taken up by dopamine neurons via a dopamine transporter (DAT), blocking Complex I in the electron transport chain of mitochondria, triggering oxidative stress and mitochondrial breakdown, and finally leading to neuron apoptosis. In Parkinson's disease, it is the loss of neurons in the substantia nigra, the dopamine-producing part of the substantia nigrostriatum system, that causes the disease. Due to the toxic effects of MPTP, it will cause the death of dopamine neurons in the substantia nigra, causing symptoms similar to Parkinson's disease.
Specific Modeling Methods
Mice: C57BL/6 ? male ? 8-12 week-old (period: 2 weeks), older mice may be more sensitive
Administration:
Acute model: 14-20 mg/kg ? ip ? 4 times a day, two hours apart
Sub-acute model: 20-30 mg/kg ? ip ? once daily for 5 days
Note
1. MPTP Hcl is dissolved in normal saline and configured when used.
2. After administration, we can observe whether the mice have symptoms such as reduced activity, staggering walking, twitching, fried hair, increased urination, etc. This behavior may last for 24-48 hours, after which the mice behave basically normally.
3. MPTP is usually sold as MPTP hydrochloride. The molecular weight of MPTP hydrochloride is 209.7. Therefore, it is recommended to take into account the presence of hydrochloride (HCl) when preparing injectable solutions. HCl has a molecular weight of 35.4 and accounts for 17% of MPTP. Thus, if a 20 mg/kg dose of MPTP is to be prepared, the MPTP hydrochloride dose administered is 20 mg kg* 1.17% = 23.4 mg/kg.
4. If multiple injections are given within 1 day, it is best to alternate the injections on both sides. If injected every day, it should be done at the same time. Before each injection, the mice need to be weighed and the dosage volume should be adjusted.
5. Modeling mice may not show behavioral defects of Parkinson's disease. Mice may show individual differences, and the success rate of modeling is generally difficult to reach 100%. Therefore nigrostriatal damage associated with gliosis should be mainly monitored in MPTP mouse studies.
6. High drug dosage/mice weighing less than 22 g/mixing of drugs from different batches/mice not adapting in advance/animal room being too cold may result in a number of deaths. It is recommended that the number of animals in each group be increased, and adjust to the optimal dose according to experimental conditions.
Modeling Indicators
Nigrostriatal injury: Tyrosine hydroxylase in the substantia nigra and striatum is reduced after successful modeling (IHC, IF, WB, etc.);
Other markers: reduction of brain neurotransmitters (DA, DOPAC, 5-HT, HVA, etc.) (detected by HPLC);
Nigrostriatal microglia (IBA1+ cells) and astrocytes (GFAP+ cells) are activated, and the number of α-syn aggregates in the substantia nigra .
Correlated Product(s): /
Opposite Product(s): HY-W013494

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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

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View Lastest Price from 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride manufacturers

Career Henan Chemical Co
Product
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride 23007-85-4
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1lg; 2kg; 5kg; 10kg; 100kg
Release date
2019-08-31

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