Wikia

Psychology Wiki

MPPP

Talk0
34,138pages on
this wiki
Revision as of 23:54, November 28, 2008 by Dr Joe Kiff (Talk | contribs)

(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)

Assessment | Biopsychology | Comparative | Cognitive | Developmental | Language | Individual differences | Personality | Philosophy | Social |
Methods | Statistics | Clinical | Educational | Industrial | Professional items | World psychology |

Biological: Behavioural genetics · Evolutionary psychology · Neuroanatomy · Neurochemistry · Neuroendocrinology · Neuroscience · Psychoneuroimmunology · Physiological Psychology · Psychopharmacology (Index, Outline)


MPPP chemical structure
MPPP

(1-methyl-4-phenylpiperidin-4-yl) propanoate
IUPAC name
CAS number
13147-09-6
ATC code

[[ATC_code_|]][1]

PubChem
61583
DrugBank
DB01478
Chemical formula {{{chemical_formula}}}
Molecular weight 247.33 g/mol
Bioavailability
Metabolism
Elimination half-life
Excretion
Pregnancy category
Legal status
Routes of administration


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 Ziering.[1] 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.[2]

1-methyl-4-phenylpyridinium (MPP+), a metabolite of MPTP, causes rapid onset of irreversible symptoms similar to Parkinson's Disease.[3][4] 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.[5]


References

  1. Ziering A, Lee J. Piperidine derivatives; 1,3-dialkyl-4-aryl-4-acyloxypiperidines. Journal of Organic Chemistry. 1947 Nov;12(6):911-4. PMID 18919744
  2. 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.
  3. 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.
  4. Surprising Clue to Parkinson's - TIME.
  5. Schmidt N, Ferger B. Neurochemical findings in the MPTP model of Parkinson's Disease. Journal of Neural Transmission. (2001) 108: 1263–1282.



This page uses Creative Commons Licensed content from Wikipedia (view authors).

Around Wikia's network

Random Wiki