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Diphenylprolinol

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Diphenylprolinol
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • diphenyl(pyrrolidin-2-yl)methanol
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.118.791Edit this at Wikidata
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 anorepinephrine-dopamine reuptake inhibitor which is used as adesigner drug.[1]

Pharmacology

[edit]

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 withglaucine in aparty pill product, thus making it impossible to say for certain which drug was responsible.[3]

Other uses

[edit]

Diphenylprolinol can be used to prepare the chiralCBS catalyst, which is used forenantioselective organic synthesis.[4]

See also

[edit]

References

[edit]
  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.Bibcode:1987JAChS.109.5551C.doi:10.1021/ja00252a056.ISSN 0002-7863.
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
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