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| ECHA InfoCard | 100.118.791  |
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| Formula | C17H19NO |
| Molar mass | 253.345 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.
Pharmacology
The dextrorotary (R)-(+)-enantiomer 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 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, which is used for enantioselective organic synthesis.
See also
- 2-Diphenylmethylpyrrolidine (Desoxy-diphenylprolinol)
- Desoxypipradrol
- Pipradrol
- Prolinol
- Corey-Bakshi-Shibata reduction
References
- 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.
- 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.
- 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.
- 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.