|Systematic (IUPAC) name|
|Synonyms||4-propionyloxy-4-phenyl-N-methylpiperidine, MPPP, 3-desmethylprodine|
|Molar mass||247.33 g/mol[[Script error: No such module "String".]]|
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 pethidine and is listed as having 70% of the potency of morphine.
The drug was first synthesised in 1977 for recreational purposes by a 23-year old graduate student named Barry Kidston. Kidston had apparently studied a 1947 paper by Albert Ziering. 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 realize this and esterified the intermediate with propionic anhydride at room temperature, MPTP was formed as a major impurity. Several days after trying this new batch of his homemade drug, Kidson developed serious PD symptoms.
1-methyl-4-phenylpyridinium (MPP+), a metabolite of MPTP, causes rapid onset of irreversible symptoms similar to Parkinson's Disease. 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.
- Ziering, A; Lee, J (1947). "Piperidine derivatives; 1,3-dialkyl-4-aryl-4-acyloxypiperidines". The Journal of organic chemistry. 12 (6): 911–4. doi:10.1021/jo01170a024. PMID 18919744.
- Johannessen, JN; Markey, SP (1984). "Assessment of the opiate properties of two constituents of a toxic illicit drug mixture". Drug and alcohol dependence. 13 (4): 367–74. doi:10.1016/0376-8716(84)90004-8. PMID 6148225.
- Gibb, Barry J. (2007). The Rough Guide to the Brain, Rough Guides Ltd., London, pg.166
- Davis, GC; Williams, AC; Markey, SP; Ebert, MH; Caine, ED; Reichert, CM; Kopin, IJ (1979). "Chronic Parkinsonism secondary to intravenous injection of meperidine analogues". Psychiatry research. 1 (3): 249–54. doi:10.1016/0165-1781(79)90006-4. PMID 298352.
- "Surprising Clue to Parkinson's - TIME". Time. 2001-06-24. Retrieved 2010-05-13.
- Schmidt, N; Ferger, B (2001). "Neurochemical findings in the MPTP model of Parkinson's disease". Journal of neural transmission (Vienna, Austria : 1996). 108 (11): 1263–82. doi:10.1007/s007020100004. PMID 11768626.
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