| Revision as of 15:57, 15 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'CAS_number').← Previous edit |
Latest revision as of 01:11, 2 September 2024 edit undo98.178.241.102 (talk) Cat. |
| (45 intermediate revisions by 34 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
|
{{cs1 config|name-list-style=vanc}} |
|
|
{{Use dmy dates|date=March 2018}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
|
|
| Watchedfields = changed |
|
|
| verifiedrevid = 460792401 |
|
| IUPAC_name = diphenyl(pyrrolidin-2-yl)methanol |
|
| IUPAC_name = diphenyl(pyrrolidin-2-yl)methanol |
|
| image = Diphenylprolinol.svg |
|
| image = Diphenylprolinol.svg |
| Line 6: |
Line 12: |
|
<!--Clinical data--> |
|
<!--Clinical data--> |
|
| tradename = |
|
| tradename = |
|
| routes_of_administration = |
|
| routes_of_administration = |
|
|
| legal_DE = NpSG |
|
|
| legal_UK = Class B |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
<!--Pharmacokinetic data--> |
|
| metabolism = |
|
| metabolism = |
|
| elimination_half-life = |
|
| elimination_half-life = |
|
| excretion = |
|
| excretion = |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|changed|CAS}} |
|
| CAS_number = <!-- blanked - oldvalue: 22348-32-9 --> |
|
| CAS_number = 22348-32-9 |
|
| ATC_prefix = none |
|
| ATC_prefix = none |
|
| PubChem = 204386 |
|
| PubChem = 204386 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 177034 |
|
| ChemSpiderID = 177034 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| C=17 | H=19 | N=1 | O=1 |
|
|
|
| UNII = 54U9UN7HN4 |
|
| molecular_weight = 253.33886 g/mol |
|
|
|
| smiles = OC(c1ccccc1)(c2ccccc2)C3NCCC3 |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 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 |
|
| StdInChI = 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 |
|
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = OGCGXUGBDJGFFY-UHFFFAOYSA-N |
|
| StdInChIKey = OGCGXUGBDJGFFY-UHFFFAOYSA-N |
|
|
|
|
|
<!--Chemical data--> |
|
⚫ |
| C=17 | H=19 | N=1 | O=1 |
|
|
|
|
}} |
|
}} |
|
|
|
|
|
'''Diphenylprolinol''' ('''D2PM'''), or (''R''/''S'')-(±)-diphenyl-2-pyrrolidinyl-methanol, is a relatively mild ] which is used as a ].<ref>Wood DM et al, Detection of the novel recreational drug Diphenyl-2-pyrrolidinemethanol (D2PM) sold legally in combination with 1-Benzylpiperzaine (BZP). ''Clinical Toxicology'' 2008; 46:393.</ref><ref></ref> |
|
'''Diphenylprolinol''' ('''D2PM'''), or (''R''/''S'')-(±)-diphenyl-2-pyrrolidinyl-methanol, is a ] which is used as a ].<ref>{{cite journal | vauthors = Wood DM, Button J, Lidder S, Ovaska H, Ramsey J, Holt DW, Dargan P | title = Detection of the novel recreational drug diphenyl-2-pyrrolidinemethanol (D2PM) sold'legally'in combination with glaucine. | journal = Clinical Toxicology | date = June 2008 | volume = 46 | issue = 5 | pages = 393 }}; {{cite journal | vauthors = | title = Abstracts of the XXVIII International Congress of the European Association of Poison Centres and Clinical Toxicologists. May 6-9, 2008. Seville, Spain | journal = Clinical Toxicology | volume = 46 | issue = 5 | pages = 351–421 | date = June 2008 | pmid = 18568796 | doi = 10.1080/15563650802071703 | s2cid = 115828300 }}</ref> |
|
|
|
|
|
==Pharmacology== |
|
==Pharmacology== |
|
The dextrorotary (''R'')-(+)-] is the most pharmacologically active, although a variety of related derivatives have been studied.<ref></ref> Anecdotally, the dextrorotary enantiomer is orally active in the 2 mg - 5 mg range as larger doses e.g. 25 mg+ would prove fatal, with a duration of 5–8 hours. The effects are said to be similar to other ]s, producing mild stimulation (at least in relation to substances like ] or ]) which is productive for working or studying, but with relatively little euphoria. Similar drugs to diphenylprolinol include ], ], and to a lesser extent, ]. |
|
The dextrorotary (''R'')-(+)-] is the more pharmacologically active, although a variety of related derivatives have been studied.<ref>{{US patent reference | url = http://www.google.com/patents/about?id=XycDAAAAEBAJ&dq=5925666 | inventor = Jackson PF, Slusher BS | assign1 = Eisai Corp of North America | title = Pharmaceutical compositions and methods for treating compulsive disorders using pyrrolidine derivatives | number = 5925666 | gdate = 20 July 1999 | postscript = . }}</ref> |
|
|
|
|
|
⚫ |
Side effects including chest pain (suggestive of possible cardiovascular toxicity) have been seen following recreational use of diphenylprolinol, although it was combined with ] in a ] product, thus making it impossible to say for certain which drug was responsible.<ref>{{cite journal | vauthors = Lidder S, Dargan P, Sexton M, Button J, Ramsey J, Holt D, Wood D | title = Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol ) | journal = Journal of Medical Toxicology | volume = 4 | issue = 3 | pages = 167–169 | date = September 2008 | pmid = 18821489 | pmc = 3550040 | doi = 10.1007/bf03161195 }}</ref> |
|
There have been indications from detailed reports posted on Internet forums dedicated to researching such compounds that diphenylprolinol may not be as benign as its mild effects seem to suggest.{{Citation needed|date=February 2010}} At higher doses and with more frequent administration, its effects on ] can become significant enough for binging and addiction to enter the picture. Several large overdoses requiring hospitalization have been reported, possibly related to addiction issues. It is advisable to exercise caution when administering this compound, even for occasional use, as most ]s are addictive. |
|
|
|
|
|
|
|
== Other uses == |
| ⚫ |
Side effects including chest pain (suggestive of possible cardiovascular toxicity) have been seen following recreational use of diphenylprolinol, although it was combined with ] in a ] product ("Head Candy" brand), thus making it impossible to say for certain which drug was responsible.<ref>{{cite journal | last1 = Lidder | first1 = S | last2 = Dargan | first2 = P | last3 = Sexton | first3 = M | last4 = Button | first4 = J | last5 = Ramsey | first5 = J | last6 = Holt | first6 = D | last7 = Wood | first7 = D | title = Cardiovascular toxicity associated with recreational use of diphenylprolinol (diphenyl-2-pyrrolidinemethanol D2PM) | journal = Journal of medical toxicology : official journal of the American College of Medical Toxicology | volume = 4 | issue = 3 | pages = 167–9 | year = 2008 | pmid = 18821489 }}</ref> |
|
|
|
Diphenylprolinol can be used to prepare the chiral ], which is used for ] organic synthesis.<ref>{{cite journal | doi = 10.1021/ja00252a056 | vauthors = Corey EJ, Bakshi RK, Shibata S | journal = ] | year = 1987 | volume = 109 | pages = 5551–5553 | issn = 0002-7863 | title = Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines Mechanism and synthetic implications | issue = 18}}</ref> |
|
|
|
|
|
== Use in organic synthesis == |
|
== See also == |
|
⚫ |
* ] (Desoxy-diphenylprolinol) |
|
In ], diphenylprolinol can be used to prepare the chiral ], which is used for ] reduction of ] ]s.<ref>{{cite journal | doi = 10.1021/ja00252a056 | author = Corey, E. J.; Bakshi, R. K.; Shibata S., | journal = ] | year = 1987 | volume = 109 | pages = 5551 | issn = 0002-7863 | title = Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines Mechanism and synthetic implications | issue = 18}}</ref> The catalyst is also useful in asymmetric ]s. Diphenylprolinol is condensed with a ], or with ] (as shown below), to give the CBS catalyst, which complexes ''in situ'' with ] to give the active catalyst.<ref>{{cite journal | doi = 10.1002/anie.199207291 | author = Lohray, B. B., Bhushan, V. | journal = ] | year = 1992 | volume = 31 | issue = 6 | pages = 729–730 | issn = 0570-0833 | title = Oxazaborolidines and Dioxaborolidines in Enantioselective Catalysis}}</ref> |
|
|
|
|
|
] |
|
|
|
|
|
==See also== |
|
| ⚫ |
* ] |
|
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
|
|
|
|
|
==References== |
|
== References == |
|
{{Reflist}} |
|
{{Reflist}} |
|
|
|
|
==External links== |
|
|
* |
|
|
|
|
|
|
{{Stimulants}} |
|
{{Stimulants}} |
|
|
{{Monoamine reuptake inhibitors}} |
|
{{Dopaminergics}} |
|
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
|
] |
|
|
] |