Diphenylprolinol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Diphenylprolinol
Diphenylprolinol.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
ECHA InfoCard 100.118.791
Chemical and physical data
Formula C17H19NO
Molar mass 253.34 g/mol
3D model (Jmol)
 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]

Pharmacology[edit]

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[edit]

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

See also[edit]

References[edit]

  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.[dead link]
  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.