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4'-Methyl-α-pyrrolidinohexiophenone: Wikis

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4'-Methyl-α-pyrrolidinohexiophenone
Systematic (IUPAC) name
1-(4-methylphenyl)-2-(1-pyrrolidinyl)-1-hexanone
Identifiers
CAS number  ?
ATC code  ?
PubChem 6423085
Chemical data
Formula C 17H25NO 
Mol. mass 259.385 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

4'-Methyl-α-pyrrolidinohexiophenone or MPHP is a stimulant compound which has been reported as a novel designer drug.[1][2] It is closely related to pyrovalerone, being simply its chain-lengthened homologue. In the pyrrolidinophenone series, stimulant activity is maintained so long as the positions of the aryl, ketone and pyrrolidinyl groups are held constant, while the alkyl backbone can be varied anywhere between three to as many as seven carbons,[3] with highest potency usually seen with the pentyl or isopentyl backbone, and a variety of substituents are tolerated on the aromatic ring.[4]

References

  1. ^ Springer D, Peters FT, Fritschi G, Maurer HH. New designer drug 4'-methyl-alpha-pyrrolidinohexanophenone: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. Journal of Chromatography B Analytical Technologies in the Biomedical and Life Sciences. 2003 Jun 5;789(1):79-91. PMID 12726846
  2. ^ Peters FT, Dragan CA, Kauffels A, Schwaninger AE, Zapp J, Bureik M, Maurer HH. Biotechnological synthesis of the designer drug metabolite 4'-hydroxymethyl-alpha-pyrrolidinohexanophenone in fission yeast heterologously expressing human cytochrome P450 2D6--a versatile alternative to multistep chemical synthesis. Journal of Analytical Toxicology. 2009 May;33(4):190-7. PMID 19470220
  3. ^ α-substituted-ketones and processes for their preparation. British Patent GB 1149366A, filed 26 May 1966.
  4. ^ Meltzer PC, Butler D, Deschamps JR, Madras BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. Journal of Medicinal Chemistry. 2006 Feb 23;49(4):1420-32. PMID 16480278
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