Diphenylprolinol Explained

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

Pharmacology

The dextrorotary (R)-(+)-enantiomer is the more pharmacologically active, although a variety of related derivatives have been studied.

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, thus making it impossible to say for certain which drug was responsible.^[2]

Other uses

Diphenylprolinol can be used to prepare the chiral CBS catalyst, which is used for enantioselective organic synthesis.^[3]

See also

• 2-Diphenylmethylpyrrolidine (Desoxy-diphenylprolinol)
• Desoxypipradrol
• Pipradrol
• Prolinol
• Corey-Bakshi-Shibata reduction

Notes and References

1. Wood DM, Button J, Lidder S, Ovaska H, Ramsey J, Holt DW, Dargan P . Detection of the novel recreational drug diphenyl-2-pyrrolidinemethanol (D2PM) sold'legally'in combination with glaucine. . Clinical Toxicology . June 2008 . 46 . 5 . 393 .

   Abstracts of the XXVIII International Congress of the European Association of Poison Centres and Clinical Toxicologists. May 6-9, 2008. Seville, Spain . Clinical Toxicology . 46 . 5 . 351–421 . June 2008 . 18568796 . 10.1080/15563650802071703 . 115828300 .

2. 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 . 4 . 3 . 167–169 . September 2008 . 18821489 . 3550040 . 10.1007/bf03161195 .
3. 10.1021/ja00252a056 . Corey EJ, Bakshi RK, Shibata S . . 1987 . 109 . 5551–5553 . 0002-7863 . Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines Mechanism and synthetic implications . 18.