Diphenylprolinol
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
  • 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)
  • OC(c1ccccc1)(c2ccccc2)C3NCCC3
  • 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 checkY
  • Key:OGCGXUGBDJGFFY-UHFFFAOYSA-N checkY
 ☒NcheckY (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]

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. ↑ 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. ↑ 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. ↑ 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. ↑ 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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