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HCID 1388Erstellt: 27. Oktober 2026

1,2,3,6-Tetrahydro-1-methyl-4-phenylpyridin

MPTP · NSC 139654 · Naphthoic Acid Impurity 111 · 1-METHYL-4-PHENYL-PIPERIDINE-3-EN · 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridin · 1,2,3,6-tetrahydro-1-methyl-4-phenylpyridine · 1,2,3,6-tetrahydro-1-methyl-4-phenyl-pyridin · 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE

https://huagongshe.com/de/chemical/1388

Molekülstruktur von 1,2,3,6-Tetrahydro-1-methyl-4-phenylpyridin

Identifikatoren & physikalische Daten

CAS No.28289-54-5
SummenformelC12H15N
Durchschnittliche Molmasse173,25 g/mol
Monoisotopische Masse173,12044948 g/mol
SMILESCN1CC=C(c2ccccc2)CC1
InChIKeyPLRACCBDVIHHLZ-UHFFFAOYSA-N
PubChem CID1388
ChEMBLCHEMBL24172
ChEBICHEBI:17963
EC No.248-939-7
DTXSIDDTXSID8040933
Lokaler Name1,2,3,6-Tetrahydro-1-methyl-4-phenylpyridin

Chemische & physikalische Eigenschaften

XLogP2,7
Polarare Oberfläche (TPSA)3,2
H-Brücken-Donoren0
H-Brücken-Akzeptoren1
Frei drehbare Bindungen1
Schwere Atome13
Formalladung0
Komplexität189
StoffklassenNitrogen Compounds -> Pyridines
ArzneimittelDEA NFLIS-Drug Category -> Narcotics
LogP (Verteilungskoeffizient)log Kow = 2.71 @ pH 7.5 (as MPP+)
Color/FormCrystals from heptane
Siedepunkt85 to 90 °C @ 0.8 mm Hg128-132 °C12 mm Hg(lit.)
Schmelzpunkt40-42 °Caprox. 36°C
Dampfdruck0.00945 [mmHg]
Physical DescriptionCrystals[HSDB]
Dichte1.001±0.06 g/cm3(Predicted)
LagerbedingungenInert atmosphere,Room Temperature
LöslichkeitChloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
pKa (Säurekonstante)8.66±0.40(Predicted)
AggregatzustandSolid
FarbePale Yellow to Light Yellow
Merck13,6319
StabilitätStable. Incompatible with strong oxidizing agents.

Sicherheit & Vorschriften

GHS-EinstufungDangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P264, P270, P301+P316, P308+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
GefahrenübersichtThe toxic effects of MPTP were discovered in 1982 when several injection drug users in San Jose, California developed frozen addict syndrome within a week of using MPPP contaminated with MPTP. The syndrome resembled idiopathic Parkinson disease, and patients showed some improvement after treatment with L-dopa. [Ford, p. 634-5] MPTP does not cause occupational parkinsonism, but it causes acute parkinsonism in humans and experimental animals after injection. The cumulative doses in animals are in the range of 1.5 to 410 mg/kg depending on the species. [See Reference #1}
Hazard Classes and CategoriesAcute Tox. 3 (100%)
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
TreatmentBecause MPTP itself is not directly harmful, toxic effects of acute MPTP poisoning can be mitigated by the administration of monoamine oxidase inhibitors (MAOIs) such as selegiline. MAOIs prevent the metabolism of MPTP to MPP+ by inhibiting the action of MAO-B, minimizing toxicity and preventing neural death. (L1670)
Unerwünschte WirkungenNeurotoxin - Parkinsonism
ToxizitätsübersichtMPTP itself is not toxic, and as a lipophilic compound can cross the blood-brain barrier. Once inside the brain, MPTP is metabolized into the toxic cation 1-methyl-4-phenylpyridinium (MPP+) by the enzyme MAO-B of glial cells. MPP+ primarily kills dopamine-producing neurons in a part of the brain called the pars compacta of the substantia nigra. MPP+ interferes with complex I of the electron transport chain, a component of mitochondrial metabolism, which leads to cell death and causes the buildup of free radicals, toxic molecules that contribute further to cell destruction. (L1670)

Anwendungen & Verwendung

Verwenden

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

Human Toxicity Excerptschemical selective damage to cells in the substantia nigra occurs following human ingestion of MPTP (1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine). ... Following iv injection of an illicit drug containing MPTP, humans developed chronic Parkinsonism, resulting from substantia nigra destruction.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Antidote and Emergency Treatment/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Toxicity DataLD50: 54 mg/kg (Subcutaneous, Mouse) (A2830)
Wassergefährdungsklasse (WGK)3
UN-TransportnummerUN 2811 6.1/PG 2
RTECS-Nr.UT8358900
R-Sätze (R)25-39/23/24/25
ToxizitätHuman toxicity originally discovered when it was an unexpected by-product from the illicit synthesis of a heroin substitute (i.e., meperidine analog). Currently used experimentally as the primary animal model for the study of Parkinson’s disease. MPTP is a neurotoxicant that is activated to 1-methyl-4-phenylpyridinium ion (MPP1) by the actions of monoamine oxidase B located in the mitochondria of brain astrocytes. The MPP1 is then transported into dopamine, and to a lesser extent, other monoaminergic neurons. Once inside these dopamine neurons in the substantia nigra, it destroys these neurons by mechanisms that may involve an oxidative cascade and/or inhibition of electron transport. Intoxication causes a parkinsonism syndrome almost identical in signs and symptoms to Parkinson’s disease, including rigidity, bradykinesia, tremor, and postural instability. In the event of known ingestion, immediate (but not delayed) administration of a monoamine oxidase inhibitor (especially one selective for MAO-B like deprenyl) and dopamine uptake inhibitor can be therapeutic.
GefahrensymboleT
Sicherheitshinweise (S)45
Gefahrenklasse6.1(b)
VerpackungsgruppeIII
Gefahrstoffdaten28289-54-5(Hazardous Substances Data)