MPPP

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IUPAC_name = (1-methyl-4-phenylpiperidin-4-yl) propanoate

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CAS_number = 13147-09-6
synonyms = 4-propionyloxy-4-phenyl-N-methylpiperidine, MPPP, 3-desmethylprodine
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PubChem = 61583
DrugBank = DB01478
C = 15 | H = 21 | N = 1 | O = 2
molecular_weight = 247.33 g/mol
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legal_US = Schedule I
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MPPP (1-methyl-4-phenyl-4-propionoxypiperidine, Desmethylprodine) is an opioid analgesic drug. It is not used in clinical practice, but has been illegally manufactured for recreational drug use. It is an analog of meperidine (Demerol), but since it is not used in medicine, the DEA has labeled it a Schedule I drug in the United States. In fact, it is the reversed ester of meperidine and is listed as having 70% of the potency of morphine.

The drug was first illicitly synthesised by a graduate student named Barry Kidston. Kidston had apparently studied a 1947 paper by Albert Zeiring. By reversing the ester of the meperidine skeleton, a drug approaching the potency of morphine was produced. However, the intermediate tertiary alcohol is liable to dehydration in acidic conditions if the reaction temperature rises above -30°C, and since Kidston did not realise this and esterified the intermediate with propanoic anhydride at room temperature, MPTP was formed as a major impurity. [Johannessen JN, Markey SP. Assessment of the opiate properties of two constituents of a toxic illicit drug mixture. "Drug and Alcohol Dependence". 1984 Jul;13(4):367-74.]

1-methyl-4-phenylpyridinium (MPP+), a metabolite of MPTP, causes rapid onset of irreversible symptoms similar to Parkinson's Disease. [Davis GC, Williams AC, Markey SP, Ebert MH, Caine ED, Reichert CM, Kopin IJ. Chronic Parkinsonism secondary to intravenous injection of meperidine analogues. "Psychiatry Research". 1979 Dec;1(3):249-54.] cite web |url=http://www.time.com/time/magazine/article/0,9171,1101850408-141542,00.html |title=Surprising Clue to Parkinson's - TIME |format= |work= |accessdate=] MPTP is metabolized to the neurotoxin MPP+ by the enzyme MAO-B, which is expressed in neurons. This selectively kills brain tissue in the area of the brain called the substantia nigra and causes Parkinsonian symptoms. [Schmidt N, Ferger B. Neurochemical findings in the MPTP model of Parkinson's Disease. "Journal of Neural Transmission". (2001) 108: 1263–1282.]

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