Diphenylprolinol

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Diphenylprolinol
Diphenylprolinol.svg
Systematic (IUPAC) name
diphenyl(pyrrolidin-2-yl)methanol
Clinical data
Legal status
Identifiers
CAS Number 22348-32-9 N
ATC code none
PubChem CID: 204386
ChemSpider 177034 YesY
Chemical data
Formula C17H19NO
Molecular mass 253.34 g/mol
  • 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 YesY
  • Key:OGCGXUGBDJGFFY-UHFFFAOYSA-N YesY
 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

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

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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