MPPP: Information from Answers.com

This article is about the opiate drug. For the stimulant α-PPP analogue, see 4'-Methyl-α-pyrrolidinopropiophenone.


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	C₁₅H₂₁N O₂
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 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 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]

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References

^ 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
^ 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.
^ 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.
^ "Surprising Clue to Parkinson's - TIME". http://www.time.com/time/magazine/article/0,9171,1101850408-141542,00.html.
^ Schmidt N, Ferger B. Neurochemical findings in the MPTP model of Parkinson's Disease. Journal of Neural Transmission. (2001) 108: 1263–1282.

Opioids (N02A)

Opium
derivatives

Whole Opium
Preparations

B & O Supprettes • Black Drop • Compote/Kompot/Polish Heroin • Diacodium Diascordium • Dover's powder • Granulated Opium • Laudanum • Mithridate • Nepenthe • Opium • Paregoric • Poppy Straw Concentrate(PSC) aka Concentrate of Poppy Straw • Poppy tea • Powdered Opium • Smoking Opium • Theriac

Natural Opiates

Narcotic Opium Alkaloids & Precursors see also: Components of Opium	Calcium Morphenate • Codeine • Dihydroneopine • Dihydronepenthone • Dihydrothebaine • Meconic Acid • Morphine • Narceine • Narcotine/Noscapine • Neopine • Nepenthone • Oripavine • Protopine • Pseudomorphine • Thebaine

Alkaloid Salts Mixtures	Pantopon • Papaveretum (Omnopon) • Tetrapon

Semi-Synthetics

Morphine-Codeine Group	Codeine • Codeine methylbromide • Codeine Barbiturate Salts • Codeine Salicylate • Heterocodeine • Isocodeine • Isomorphine • Morphine • Myrophine • Nalodeine • Normorphine • Morpholinylethylmorphine (Pholcodine) • Transisocodeine

Codeine Analogues	Benzylmorphine • Ethylmorphine (Dionine) (Codethyline, Dionine, &c.) • Propylmorphine

Dihydrocodeine Series	Acetyldihydrocodeine • Dihydrocodeine • Dihydroisocodeine • 7,8-dihydroisocodeine • Diacetyldihydrocodeine • Dihydrocodeine • Dihydroisocodeine • Nicocodeine • Nicodicodeine • Thebacetyl

Hydrocodone-Oxycodone Series (Codeineones)	1-carbethoxy-14-hydroxydihydrocodeinone • 1-carboxy-14-hydroxydihydrocodeinone • 7,8-dihydrocodeineone • Bromoisopropyldihydrocodeinone • Codeinone • Acetyldihydrocodeinone (Dihydrocodeinone enol acetate) • Hydrocodone • Monodihydrocodeineone • Noroxycodone • Propropyldihydrocodeinone • Oxycodone • Thebacon

Morphones (Morphinone Group)	14-Ethoxymetopon • 14-Methoxymetopon • 14-O-Methyloxymorphone • 14-Phenylpropoxymetopon • 14-phenylpropoxy-5-methyl-hydromorphone • 14ß-Hydroxymorphone • 7-Spiroindanyloxymorphone • 8,14-Dihydroxydihydromorphinone • Acetylmorphone • Bromoisopropropyldihydromorphinone • Codorphone • Hydromorphinone (Monohydromorphinone) • Hydromorphone • Isopropropyldihydrocodeinone • Isopropropyldihydromorphinone • Methyldihydromorphinone • Metopon • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxymorphone • Pentamorphone • Semorphone •

Morphinols & Morphols incl. Dihydroneopine Group	14-Hydroxydihydrocodeine • 14-Hydroxymorphine • 14-Hydroxydihydroisocodeine • 14-hydroxydihydrocodeine (Oxycodeine [sic]) • 14ß-Hydroxyisomorphine • 14ß-Hydroxymorphine 6-Hydrocodol • 6 beta-Oxymorphol • Alphahydrocodol/α-hydrocodol (Dihydroneopine) • Hydrocodol (Dihydroneopine) • Hydromorphinol • Hydromorphol • Morphinol • Morphol • N-demethyl14-hydroxydihydrocodeine • Oxymorphinol • Oxymorphol

Morphides	α-chlorocodide (Alphachlorocodide/Chlorocodide) • α-chloromorphide • Bromocodide • Bromomorphide(8-Bromomorphide, 3-Bromomorphide) • Chlorocodide • Chloromorphide • Codide • Fluorocodide(8-Fluorocodide) • Fluormorphide • Iodocodide • Iodomorphide (8-Iodomorphide) • Morphide

Misc. Substituted Morphine Derivatives	2-(p-Nitrophenyl)-4-isopropylmorphine 2,4-Dinitrophenylmorphine N-Phenethylnormorphine

Dihydromorphine Group	6-Acetyldihydromorphine • 6-Monoacetyldihydromorphine • 6-Monoacetyldihydrocodeine • 6-Methyldihydromorphine • Acetyldihydromorphine • Dihydroisomorphine • Dihydromorphine • Ethyldihydromorphine • Ethyldihydromorphinone • Hydroxycodeine • Methyldihydromorphine (Dihydroheterocodeine)

Bentley Compounds (Etorphine Group)	6,14-Endoethenotetrahydrooripavine • BU-48 • Acetorphine • Alletorphine • Butorphine • Dihydroetorphine • Etorphine • Cyprenorphine • Diprenorphine (M5050) • N-cyclopropylmethyl-noretorphine

Desomorphine-Codoxime Group	6-Methylenedihydrodesoxymorphine • Azidomorphine • Codoxime • Desocodeine • Dihydrodesoxycodeine/Desocodeine • Dihydrodesoxymorphine (Desomorphine) • Methyldesorphine

Heroin-MAM-Nicomorphine Group (3- and/or 6- esters)	3-Monoacetylmorphine • 6-Monoacetylmorphine • 6-Mononicotinoylmorphine • Acetylcodeine • Acetylpropionylmorphine(Monoacetylpropionylmorphine) • α-diacetylmorphine • Diacetylcodeine • Diacetyldihydrocodeine • Diacetyldihydromorphine (Dihydroheroin) • Diacetylheterocodeine • Diacetylisocodeine • Diacetylisomorphine • Diacetyl-N-cyanomorphine • Diacetylpropionylmorphine • Dibenzylmorphine • Dibutanoylmorphine • Dipropanoylmorphine • Disalicyloylmorphine • Heroin-7,8-Oxide • Heroin (Diacetylmorphine) • Monoacetylmorphine • Nicocodeine • Nicodicodeine • Nicodimorphine (Nicodihydromorphine) • Nicomorphine •

Nitrogen Morphine Derivatives	1-Nitrocodeine 14-hydroxydihydrocodeineN-oxide • 2-Nitromorphine • Codeine-N-Oxide • Heroin-N-Oxide • Hydromorphone-N-Oxide • Morphine-N-Oxide Oxycodone N-oxide

Halogenated Morphine Derivatives	1-Bromocodeine • 1-Bromodihydrocodeine • 1-Bromodihydrocodeinone • 1-Bromodihydromorphine • 1-Bromodihydromorphinone • 1-Bromoheroin • 1-Chlorocodeine • 1-Chlorodihydrocodeine • 1-Chlorodihydrocodeinone • 1-Chlorodihydromorphine • 1-Chlorodihydromorphinone • 1-Chloroheroin • 1-Fluorocodeine • 1-Fluorodihydrocodeine • 1-Fluorodihydrocodeinone • 1-Fluorodihydromorphine • 1-Fluorodihydromorphinone • 1-Fluoroheroin • 1-Iodocodeine • 1-Iododihydrocodeine • 1-Iododihydrocodeinone • 1-Iododihydromorphine • 1-Iododihydromorphinone • 1-Iodoheroin • 14-Chlorocodeine • 14-Fluorodihydromorphinone • 2-Chloromorphine • 6ß-Chlorocodeine

Morphazones	Acetylmorphazone • Hydromorphazone • Morphazone • Oxymorphazone

Other Morphine Derivatives	7-PET • 6ß-Thiomorphine • Acetomorphine • Apocodeine • Apomorphine • Chlornaltrexamine • Cyclocodeine • Cyclomorphine • Dicodeine Dimorphine N-N-Propylapomorphine • Pentacodeine • Pentamorphine • Pseudomorphine • Pseudocodeine • Tetracodeine • Tetramorphine • Tricodeine • Trimorphine

Derivatives of Thebaine	1-Bromothebaine • 1-Iodothebaine • 1-Fluorothebaine • 2'-Chlorothebaine • 2'-Methylthebaine • 7-Chlorothebaine • Tetrahydrothebaine

Derivatives of Oripavine	Nepenthone • Thevinone •

Derivatives of Other Opium Alkaloids	α-Dihydroneopine • Dihydroneopine

Active Opiate
Metabolites

Codeine-N-Oxide (Genocodeine) • Hydromorphone-N-Oxide • Heroin-7,8-Oxide • Morphine-3-glucuronide • Morphine-6-glucuronide • Monoacetylmorphine • Morphine-N-Oxide (Genomorphine) • Naltrexol • Norcodeine • Normorphine

Morphinans

Morphinan Series	4-chlorophenylpyridomorphinan • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dimemorfan • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • N-Methylmorphinan • Oxilorphan • Phenomorphan • Methorphan / Racemethorphan • Racemorphan • Ro4-1539 • Stephodeline • Xorphanol

Buprenorphine Group	Buprenorphine • 18,19-Dehydrobuprenorphine (HS-599) • Norbuprenorphine • Thienorphine

Others	1-Nitroaknadinine • 14-episinomenine • 5,6-Dihydronorsalutaridine • 6-Ketonalbuphine • Aknadinine • Butorphanol • Cephakicine • Cephasamine • Cyprodime • Drotebanol • Fenfangjine G • Nalbuphine • Sinococuline • Sinomenine (Cocculine) • Tannagine

Benzomorphans

5,9-DEHB • Allylnormetazocine • Anazocine • Bremazocine • Cogazocine • Cyclazocine • Dezocine • Eptazocine • Etazocine • Ethylketocyclazocine • Fluorophen • Ketazocine • Metazocine • Pentazocine • Phenazocine • Quadazocine • Thiazocine • Tonazocine • Volazocine • Zenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Hydroxymethoxypethidine • Morpheridine • Oxpheneridine (Carbamethidine) • Meperidine-N-Oxide • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine

Prodines	Allylprodine • Isopromedol • Meprodine (α-meprodine / β-meprodine) • MPPP (Desmethylprodine) • PEPAP • Prodine (α-prodine / β-prodine) • Prosidol • Trimeperidine (Promedol)

Ketobemidones	Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone

Others	Alvimopan • Loperamide • Phenadone • Picenadol • tecodine

Open Chain
Opioids

Amidones	Dextromethadone • Dextroisomethadone • Dipipanone • Hexalgon (Norpipanone) • Isomethadone • Levoisomethadone • Levomethadone • Methadone • Methadone intermediate • Normethadone • Norpipanone • Phenadoxone (Heptazone) • Pipidone

Methadols	Dimepheptanol (Racemethadol) • Levacetylmethadol • Levomethadyl acetate (Acetylmethadol) • Noracetylmethadol

Moramides	Dextromoramide • Levomoramide • Moramide intermediate • Racemoramide

Thiambutenes	Diethylthiambutene (Themalon) • Dimethylthiambutene • Ethylmethylthiambutene • Piperidylthiambutene • Pyrrolidinylthiambutene • Thiambutene • Tipepidine

Phenalkoxams	Dextropropoxyphene (Propoxyphene) • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Norpropoxyphene

Ampromides	Diampromide • Phenampromide • Propiram

Tilidine Group	Bisnortilidine • Nortilidine • Prodilidine • Tilidine •

Others	IC-26 • Isoaminile • Lefetamine • R-4066

Anilidopiperidines

3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • Benzylfentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thalamonial • Thenylfentanyl • Thiofentanyl • Trefentanil

Oripavine-derived
Synthetics

6,14-Endoethenotetrahydrooripavine • 7-PET • Acetorphine • Alletorphine • BU-48 • Buprenorphine • Butorphine • Cyprenorphine • Dihydroetorphine • Diprenorphine (M5050) • Etorphine • 18,19-Dehydrobuprenorphine (HS-599) • N-cyclopropylmethyl-noretorphine • Nepenthone • Norbuprenorphine • Thevinone • Thienorphine

Phenazepines

Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine

Pirinitramides

Bezitramide • Piritramide

Benzimidazoles

Clonitazene • Etonitazene • Nitazene

Indoles

18-MC • 7-Acetoxymitragynine • 7-Hydroxymitragynine • Akuammidine • Akuammine • Eseroline • Hodgkinsine • Ibogaine • Mitragynine • Noribogaine • Pericine • ψ-Akuammigine

Diphenylmethylpiperazines

BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80

Opioid peptides
see also: The Opioid Peptides

Casomorphin • DADLE • DALDA • DAMGO • Dermenkephalin • Dermorphin • Deltorphin • DPDPE • Dynorphin • Endomorphin • Endorphin • Enkephalin • Gliadorphin • Morphiceptin • Nociceptin • Octreotide • Opiorphin • Rubiscolin • TRIMU 5

Tramadol Group

O-Desmethyltramadol • Tapentadol • Tramadol •

Others

Estocine • Azaprocin • BDPC • Befiradol • BRL-52537 • C-8813 • Ciramadol • Enadoline • Faxeladol • Herkinorin • J-113,397 • JTC-801 • Methopholine • NNC 63-0532 • Phenadone • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tecodine • Tifluadom • Viminol • W-18 • Zipeprol

Opioid Antagonists
&
Inverse-Agonists

5'-Guanidinonaltrindole • β-Funaltrexamine • 6β-Naltrexol • Alvimopan • Amiphenazole • Binaltorphimine • Chlornaltrexamine • Clocinnamox • Cyclazocine • Cyprodime • Diprenorphine (M5050) • Fedotozine • JDTic • Levallorphan • Methocinnamox • Methylnaltrexone • Nalfurafine • Nalmefene • Nalmexone • Naloxazone • Naloxonazine • Naloxone • Naloxone benzoylhydrazone • Nalorphine • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan • S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM)

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	4'-methyl-α-pyrrolidinopropiophenone

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