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MPPP
Systematic (IUPAC) name
(1-methyl-4-phenylpiperidin-4-yl) propanoate
Identifiers
CAS number 13147-09-6
ATC code  ?
PubChem 61583
DrugBank DB01478
Chemical data
Formula C 15H21NO2  
Mol. mass 247.33 g/mol
Synonyms 4-propionyloxy-4-phenyl-N-methylpiperidine, MPPP, 3-desmethylprodine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US)
Routes  ?

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 pethidine (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 for recreational purposes 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 realize this and esterified the intermediate with propionic 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 (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.   edit
  2. ^ Johannessen, JN; Markey (1984). "Assessment of the opiate properties of two constituents of a toxic illicit drug mixture". Drug and alcohol dependence 13 (4): 367–74. PMID 6148225.   edit
  3. ^ Davis, GC; Williams; Markey; Ebert; Caine; Reichert; Kopin (1979). "Chronic Parkinsonism secondary to intravenous injection of meperidine analogues". Psychiatry research 1 (3): 249–54. PMID 298352.   edit
  4. ^ "Surprising Clue to Parkinson's - TIME". http://www.time.com/time/magazine/article/0,9171,1101850408-141542,00.html.  
  5. ^ Schmidt, N; Ferger (2001). "Neurochemical findings in the MPTP model of Parkinson's disease". Journal of neural transmission (Vienna, Austria : 1996) 108 (11): 1263–82. PMID 11768626.   edit

Wiktionary

Up to date as of January 15, 2010

Definition from Wiktionary, a free dictionary

Contents

English

Initialism

MPPP

  1. 4'-methyl-alpha-pyrrolidinopropiophenone

Noun

Singular
MPPP

Plural
uncountable

MPPP (uncountable)

  1. (pharmacology) Synthetic heroin of the pyrrolidinophenone type.

Quotations

  • 2005 Jun; Staack et al, Current Drug Metabolism [1]
    Furthermore, N-benzylpiperazine (BZP), 1-(3, 4-methylenedioxybenzyl)piperazine (MDBP), 1-(3-trifluoromethylphenyl)piperazine (TFMPP), 1-(3-chlorophenyl)piperazine (mCPP) and 1-(4-methoxyphenyl)piperazine (MeOPP) were taken into consideration as derivatives of the class of piperazine-derived designer drugs, as well as alpha-pyr-rolidinopropiophenone (PPP), 4'-methoxy-alpha-pyrrolidinopropiophenone (MOPPP), 3', 4'-methylenedioxy-alpha-pyrrolidino-propiophenone (MDPPP), 4'-methyl-alpha-pyrrolidinopropiophenone (MPPP), and 4'-methyl-alpha-pyrrolidinoexanophenone (MPHP) as derivatives of the class of alpha-pyrrolidinophenone-derived designer drugs.
  • 2003 Springer et al, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. [2]
    The same toxicological detection procedure can be applied to other designer drugs of the pyrrolidinophenone type, like MOPPP, MDPPP, MPHP, and MPPP. The detection of the latter will also be presented here







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