Diphenylprolinol (D2PM), or (''R''/''S'')-(±)-diphenyl-2-pyrrolidinyl-methanol, is a
norepinephrine-dopamine reuptake inhibitor which is used as a
designer drug
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Des ...
.
Pharmacology
The dextrorotary (''R'')-(+)-
enantiomer
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
is the more pharmacologically active, although a variety of related derivatives have been studied.
Side effects including chest pain (suggestive of possible cardiovascular toxicity) have been seen following recreational use of diphenylprolinol, although it was combined with
glaucine
Glaucine is an aporphine alkaloid found in several different plant species in the family Papaveraceae such as ''Glaucium flavum'', '' Glaucium oxylobum'' and '' Corydalis yanhusuo'', and in other plants like ''Croton lechleri'' in the family Euph ...
in a
party pill product, thus making it impossible to say for certain which drug was responsible.
Other uses
Diphenylprolinol can be used to prepare the chiral
CBS catalyst
The CBS catalyst or Corey–Bakshi–Shibata catalyst is an Chiral synthesis, asymmetric catalyst derived from proline. It finds many uses in organic reactions such as the CBS reduction, Diels-Alder reactions and (3+2) cycloadditions. Pro ...
, which is used for
enantioselective
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical anti ...
organic synthesis.
See also
*
2-Diphenylmethylpyrrolidine (Desoxy-diphenylprolinol)
*
Desoxypipradrol
Desoxypipradrol, also known as 2-diphenylmethylpiperidine (2-DPMP), is a drug developed by Ciba in the 1950s which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI).
Chemistry
Desoxypipradrol is closely related on a structural lev ...
*
Pipradrol
Pipradrol (Meratran) is a mild central nervous system stimulant ( norepinephrine-dopamine reuptake inhibitor) that is no longer widely used in most countries due to concerns about its abuse potential. Pipradrol is still used in some European cou ...
*
Prolinol
Prolinol is a chiral amino-alcohol that is used as a chiral building block in organic synthesis. It exists as two enantiomers: the D and L forms.
Preparation
Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydri ...
*
Corey-Bakshi-Shibata reduction
References
{{Monoamine reuptake inhibitors
Tertiary alcohols
Stimulants
Norepinephrine–dopamine reuptake inhibitors
Phenylethanolamines
Pyrrolidines
Designer drugs
Benzhydryl compounds