Desmethylprodine

Desmethylprodine
Clinical data
Other names	4-propionyloxy-4-phenyl-N-methylpiperidine, MPPP, 3-desmethylprodine
Legal status
Legal status	US: Schedule I;
Identifiers
	IUPAC name (1-methyl-4-phenylpiperidin-4-yl) propanoate;
CAS Number	13147-09-6;
PubChem CID	61583;
DrugBank	DB01478;
ChemSpider	55493 ;
CompTox Dashboard (EPA)	DTXSID80157061 ;
Chemical and physical data
Formula	C15H21NO2
Molar mass	247.33 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OC2(c1ccccc1)CCN(C)CC2)CC;
	InChI InChI=1S/C15H21NO2/c1-3-14(17)18-15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3 ; Key:BCQMRZRAWHNSBF-UHFFFAOYSA-N ;
	(verify)

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.^[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] Several days after trying this new batch of his homemade drug, Kidson developed serious PD symptoms.^[3]

1-methyl-4-phenylpyridinium (MPP+), a metabolite of MPTP, causes rapid onset of irreversible symptoms similar to Parkinson's Disease.^[4]^[5] 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.^[6]

References

^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 18919744, please use {{cite journal}} with |pmid=18919744 instead.
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 6148225, please use {{cite journal}} with |pmid=6148225 instead.
^ Gibb, Barry J. (2007). The Rough Guide to the Brain, Rough Guides Ltd., London, pg.166
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 298352, please use {{cite journal}} with |pmid=298352 instead.
^ Wallis, Claudia (2001-06-24). "Surprising Clue to Parkinson's - TIME". Time. Retrieved 2010-05-13.
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 11768626, please use {{cite journal}} with |pmid=11768626 instead.

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[1] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 18919744, please use {{cite journal}} with |pmid=18919744 instead.

[2] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 6148225, please use {{cite journal}} with |pmid=6148225 instead.

[3] Gibb, Barry J. (2007). The Rough Guide to the Brain, Rough Guides Ltd., London, pg.166

[4] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 298352, please use {{cite journal}} with |pmid=298352 instead.

[urlSurprising_Clue_to_Parkinsons_-_TIME-5] Wallis, Claudia (2001-06-24). "Surprising Clue to Parkinson's - TIME". Time. Retrieved 2010-05-13.

[6] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 11768626, please use {{cite journal}} with |pmid=11768626 instead.

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