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Diphenylprolinol
Systematic (IUPAC) name
diphenyl(pyrrolidin-2-yl)methanol
Identifiers
CAS number 22348-32-9
ATC code none
PubChem 204386
Chemical data
Formula C17H19NO 
Mol. mass 253.33886 g/mol
Therapeutic considerations
Pregnancy cat.  ?
Legal status

Diphenylprolinol (D2PM), or (R/S)-(±)-diphenyl-2-pyrrolidinyl-methanol, is a relatively mild dopamine and norepinephrine reuptake inhibitor which is used as a designer drug.[1][2]

Contents

Pharmacology

The dextrorotary (R)-(+)-enantiomer is the most pharmacologically active, although a variety of related derivatives have been studied.[3] Anecdotally, the dextrorotary enantiomer is orally active in the 25-100mg range, with a duration of 5-8 hours. The effects are said to be similar to other NDRIs, producing mild stimulation (at least in relation to substances like methamphetamine or cocaine) which is productive for working or studying, but with relatively little euphoria. Similar drugs to diphenylprolinol include pipradrol, desoxypipradrol, and to a lesser extent, methylphenidate.

There have been indications from detailed reports posted on Internet forums dedicated to researching such compounds that diphenylprolinol may not be as benign as its mild effects seem to suggest.[citation needed] At higher doses and with more frequent administration, its effects on dopamine can become significant enough for binging and addiction to enter the picture. Several large overdoses requiring hospitalization have been reported, possibly related to addiction issues. It is advisable to exercise caution when administering this compound, even for occasional use, as most dopamine reuptake inhibitors are addictive.

Side effects including chest pain (suggestive of possible cardiovascular toxicity) have been seen following recreational use of diphenylprolinol, although it was combined with glaucine in a party pill product ("Head Candy" brand), thus making it impossible to say for certain which drug was responsible.[4]

Use in organic synthesis

In organic synthesis, diphenylprolinol can be used to prepare the chiral CBS catalyst, which is used for enantioselective reduction of prochiral ketones.[5] The catalyst is also useful in asymmetric Aldol reactions. Diphenylprolinol is condensed with a phenylboronic acid, or with borane (as shown below), to give the CBS catalyst, which complexes in situ with borane to give the active catalyst.[6]

Diphenylprolinol CBScatalyst.gif

See also

References

  1. ^ Wood DM et al, Detection of the novel recreational drug Diphenyl-2-pyrrolidinemethanol (D2PM) sold legally in combination with 1-Benzylpiperzaine (BZP). Clinical Toxicology 2008; 46:393.
  2. ^ Davies S. Drug Trends and New Designer Drugs. St George's University of London. 6th November 2008.
  3. ^ Paul F. Jackson et al. Pharmaceutical compositions and methods for treating compulsive disorders using pyrrolidine derivatives. US Patent 5295666
  4. ^ Lidder S, Dargan P, Sexton M, Button J, Ramsey J, Holt D, Wood D. Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol [D2PM]). Journal of Medical Toxicology. 2008 Sep;4(3):167-9. PMID 18821489
  5. ^ Corey, E. J.; Bakshi, R. K.; Shibata S., (1987). "Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines Mechanism and synthetic implications". J. Am. Chem. Soc. 109: 5551. ISSN 0002-7863. 
  6. ^ Lohray, B. B., Bhushan, V. (1992). "Oxazaborolidines and Dioxaborolidines in Enantioselective Catalysis". Angew. Chem.-Int. Edit. Engl. 31 (6): 729-730. ISSN 0570-0833. 

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