Diphenylprolinol

Diphenylprolinol

Diphenylprolinol

Chemical compound

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

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Pharmacology

The dextrorotary (R)-(+)-enantiomer is the more pharmacologically active, although a variety of related derivatives have been studied.[2]

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.[3]

Other uses

Diphenylprolinol can be used to prepare the chiral CBS catalyst, which is used for enantioselective organic synthesis.[4]

See also

References

  1. [1]
    Wood DM, Button J, Lidder S, Ovaska H, Ramsey J, Holt DW, Dargan P (June 2008). "Detection of the novel recreational drug diphenyl-2-pyrrolidinemethanol (D2PM) sold'legally'in combination with glaucine". Clinical Toxicology. 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. doi:10.1080/15563650802071703. PMID 18568796. S2CID 115828300.
  2. [2]
    US patent 5925666, Jackson PF, Slusher BS, "Pharmaceutical compositions and methods for treating compulsive disorders using pyrrolidine derivatives", issued 20 July 1999, assigned to Eisai Corp of North America.
  3. [3]
    Lidder S, Dargan P, Sexton M, Button J, Ramsey J, Holt D, Wood D (September 2008). "Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol [D2PM])". Journal of Medical Toxicology. 4 (3): 167–169. doi:10.1007/bf03161195. PMC 3550040. PMID 18821489.
  4. [4]
    Corey EJ, Bakshi RK, Shibata S (1987). "Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines Mechanism and synthetic implications". J. Am. Chem. Soc. 109 (18): 5551–5553. doi:10.1021/ja00252a056. ISSN 0002-7863.
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