Diphenylprolinol
 | |
| Clinical data | |
|---|---|
| ATC code |
|
| Legal status | |
| Legal status | |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.118.791 |
| Chemical and physical data | |
| Formula | C17H19NO |
| Molar mass | 253.345 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (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]
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 with glaucine in a party 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 chiral CBS catalyst, which is used for enantioselective organic synthesis.[4]
See also
[edit]- 2-Diphenylmethylpyrrolidine (Desoxy-diphenylprolinol)
- Desoxypipradrol
- Pipradrol
- Prolinol
- Corey-Bakshi-Shibata reduction
References
[edit]- ^ 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.