Diphenylprolinol

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

Diphenylprolinol
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
IUPAC name
  • diphenyl(pyrrolidin-2-yl)methanol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.118.791
Chemical and physical data
FormulaC17H19NO
Molar mass253.345 g·mol−1
3D model (JSmol)
SMILES
  • OC(c1ccccc1)(c2ccccc2)C3NCCC3
InChI
  • InChI=1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2 Y
  • Key:OGCGXUGBDJGFFY-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Pharmacology

The dextrorotary (R)-(+)-enantiomer is the more 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

References
  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 (5): 393. doi:10.1080/15563650802071703. PMID 18568796.
  2. Davies S. Drug Trends and New Designer Drugs. St George's University of London. 6 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. PMC 3550040. 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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