Diphenylprolinol
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| Systematic (IUPAC) name | |
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diphenyl(pyrrolidin-2-yl)methanol
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| Identifiers | |
| CAS Number | 22348-32-9  |
| ATC code | None |
| PubChem | CID 204386 |
| ChemSpider | 177034  |
| Chemical data | |
| Formula | C17H19NO |
| Molar mass | 253.34 g/mol |
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Diphenylprolinol (D2PM), or (R/S)-(±)-diphenyl-2-pyrrolidinyl-methanol, is a norepinephrine-dopamine reuptake inhibitor which is used as a designer drug.[1][2]
Contents
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]
- 2-Diphenylmethylpyrrolidine (Desoxy-diphenylprolinol)
- Desoxypipradrol
- Pipradrol
- Prolinol
- Corey-Bakshi-Shibata reduction
References[edit]
- ^ 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.
- ^ Davies S. Drug Trends and New Designer Drugs. St George's University of London. 6th November 2008.[dead link]
- ^ US patent 5925666, Paul F. Jackson et al., "Pharmaceutical compositions and methods for treating compulsive disorders using pyrrolidine derivatives"
- ^ 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.
- ^ 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.
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