Clinical data
ATC code none
Legal status
Legal status
CAS Number 22348-32-9 N
PubChem (CID) 204386
ChemSpider 177034 YesY
ECHA InfoCard 100.118.791
Chemical and physical data
Formula C17H19NO
Molar mass 253.34 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

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


The dextrorotary (R)-(+)-enantiomer is the most pharmacologically active, although a variety of related derivatives have been studied.[3]

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.[4]

Other uses

Diphenylprolinol can be used to prepare the chiral CBS catalyst, which is used for enantioselective organic synthesis.[5]

See also


  1. Wood DM, et al. (2008). "Detection of the novel recreational drug Diphenyl-2-pyrrolidinemethanol (D2PM) sold legally in combination with 1-Benzylpiperzaine (BZP)". Clinical Toxicology. 46: 393. doi:10.1080/15563650802071703. PMID 18568796.
  2. Davies S. Drug Trends and New Designer Drugs. St George's University of London. 6th November 2008.
  3. US patent 5925666, Paul F. Jackson et al., "Pharmaceutical compositions and methods for treating compulsive disorders using pyrrolidine derivatives"
  4. Lidder, S; Dargan, P; Sexton, M; Button, J; Ramsey, J; Holt, D; Wood, D (2008). "Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol D2PM)". Journal of Medical Toxicology. 4 (3): 167–9. doi:10.1007/bf03161195. 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 (18): 5551–5553. doi:10.1021/ja00252a056. ISSN 0002-7863.

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