| Revision as of 20:48, 1 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wik |
Latest revision as of 02:12, 8 October 2024 edit 76.174.0.57 (talk) See also. |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 447380381 |
|
|
|
| Watchedfields = changed |
| ⚫ |
| IUPAC_name = (''RS'')-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide |
|
|
⚫ |
| verifiedrevid = 447920554 |
|
| image = Phenylpiracetam.svg |
|
|
⚫ |
| IUPAC_name = 2-(2-oxo-4-phenylpyrrolidin-1-yl)acetohydrazide |
| ⚫ |
| width = 200px |
|
|
|
| image = Fonturacetam hydrazide.svg |
|
| imagename = 1 : 1 mixture (racemate) |
|
|
⚫ |
| width = 175px |
| ⚫ |
| drug_name = Phenotropil |
|
|
|
| chirality = ] |
|
⚫ |
| drug_name = |
|
|
| synonyms = Fonturacetam hydrazide |
|
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
|
| tradename = |
|
| tradename = Phenylpiracetam hydrazide |
|
| pregnancy_category = ? |
|
| pregnancy_category = Unknown |
|
|
| legal_US = Not FDA approved; unscheduled |
|
| legal_status = Legal to import |
|
|
| routes_of_administration = Oral |
|
| routes_of_administration = Oral |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
<!--Pharmacokinetic data--> |
|
| bioavailability = ~100 % |
|
| bioavailability = |
|
| metabolism = None |
|
| metabolism = |
|
| elimination_half-life = 3-5 hours |
|
| elimination_half-life = |
|
| excretion = Urine ~40% bile and perspiration ~60% |
|
| excretion = |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = |
|
| CAS_number = 77472-70-9 |
|
| CAS_number = 77472-71-0 |
|
| ATC_prefix = none |
|
| ATC_prefix = none |
|
| PubChem = 132441 |
|
| PubChem = 4995664 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
|
| DrugBank = |
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
| ChemSpiderID = 4175636 |
|
|
| UNII = 289199VKN4 |
|
|
|
|
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=12 | H=14 | N=2 | O=2 |
|
| C=12 | H=15 | N=3 | O=2 |
|
|
| smiles = c1ccc(cc1)C2CC(=O)N(C2)CC(=O)NN |
|
| molecular_weight = 218.3 g/mol |
|
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| smiles = C1=CC=CC=C1C2CN(C(C2)=O)CC(=O)N |
|
|
|
| StdInChI = 1S/C12H15N3O2/c13-14-11(16)8-15-7-10(6-12(15)17)9-4-2-1-3-5-9/h1-5,10H,6-8,13H2,(H,14,16) |
|
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
| StdInChIKey = AXQUMNYYLGUJIZ-UHFFFAOYSA-N |
|
|
| boiling_point = |
|
}} |
|
}} |
|
|
|
|
|
|
'''Phenylpiracetam hydrazide''', also known as '''fonturacetam hydrazide''',<ref>{{cite journal |date=2010 |title=International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 63 |url=http://apps.who.int/medicinedocs/documents/s17753en/s17753en.pdf |url-status=dead |journal=WHO Drug Information |volume=24 |issue=1 |page=56 |archive-url=https://web.archive.org/web/20140521143204/http://apps.who.int/medicinedocs/documents/s17753en/s17753en.pdf |archive-date=May 21, 2014 |access-date=26 November 2015}}</ref> is a ] that is a ] of ] in which the ] group is replaced with a ] group. It was first reported by a Russian research group in 1980 as part of a series of chemical compounds investigated as ]s.<ref name=Glozman>{{cite journal | title = Synthesis and anticonvulsive activity of 4-phenyl-2-pyrrolidinone-1-acetic acid amides | vauthors = Glozman OM, Morozov IS, Zhmurenko LA, Zagorevskii VA | journal = Khimiko-Farmatsevticheskii Zhurnal | date = 1980 | volume = 14 | issue = 11 | pages = 43–48 | language = ru | url = https://scholar.google.com/scholar?cluster=10526217948349188956}}</ref> In an electroshock test it was found to have an ] of 310{{nbsp}}mg/kg.<ref name=Glozman/> |
|
'''Phenotropil''' (]<sub>12</sub>]<sub>14</sub>]<sub>2</sub>]<sub>2</sub>, ''2-(4-phenyl-2-oxopyrrolidin-1-yl)acetamide'') is a derivative of the ] drug (R/S)-4-pheyl-2-pyrrolidon. It was developed in ], and a small number of low-scale clinical studies have shown possible links between prescription of carphedon and improvement in a number of ] conditions, including ]s of cerebral blood pathways, and certain types of ]. It is also claimed to increase physical stamina and provide improved tolerance to cold. As a result, it appears on the lists of banned substances issued by the ]. This list is applicable in all Olympic sports. As of 27 February 2006, the most recent confirmed case of carphedon use by a professional athlete is that of Russian ] Olympic ]ist ] in the ], who was disqualified from attending further events following a ]. She was subsequently banned from competition for two years. It may be noteworthy that Pyleva claims that carphedon was an unlisted ingredient of a Russian medication she was prescribed by her personal doctor (not a team doctor). |
|
|
|
|
|
|
|
== Sale on the internet == |
|
In August 2008, Russian steeplechase runner Roman Usov was pulled out of the ] for what media reported was a possible positive test for Carphedon.<ref>CNN, , Retrieved on 2008-08-09.</ref> |
|
|
|
All piracetam derivatives are not permitted to be sold as dietary supplements in the United States.<ref>{{cite journal | vauthors = Cohen PA, Zakharevich I, Gerona R | title = Presence of Piracetam in Cognitive Enhancement Dietary Supplements | journal = JAMA Internal Medicine | volume = 180 | issue = 3 | pages = 458–459 | date = March 2020 | pmid = 31764936 | pmc = 6902196 | doi = 10.1001/jamainternmed.2019.5507 | s2cid = 208274670 }}</ref> However, because they lack scheduling, piracetam derivatives like phenylpiracetam hydrazide are sold over the clear net accompanied by indications stating that the compound is "not for human consumption".<ref>{{cite journal | vauthors = Musselman ME, Hampton JP | title = "Not for human consumption": a review of emerging designer drugs | journal = Pharmacotherapy | volume = 34 | issue = 7 | pages = 745–757 | date = July 2014 | pmid = 24710806 | doi = 10.1002/phar.1424 | s2cid = 10279777 | doi-access = free }}</ref> |
|
|
|
|
|
⚫ |
== See also == |
|
A former rider for ], professional cyclist Danilo Hondo, tested positive to this banned substance in 2005. |
|
|
|
* ] |
|
|
* ] |
|
|
|
|
|
⚫ |
== References == |
|
While not widely available in the ], in ] it is available as a prescription medicine under the ] "Phenotropil". Packets of ten 100 ] pills are available for roughly 350 ] (2011 price), or about 12 USD. It is typically prescribed as a general ] or to increase tolerance to cold and stress. |
|
|
|
{{Reflist|2}} |
|
|
|
|
|
|
{{Racetams}} |
| ⚫ |
==See also== |
|
|
* ] |
|
|
|
|
|
|
⚫ |
] |
|
<gallery> |
|
|
⚫ |
] |
|
<!-- Deleted image removed: File:Phenotropil.jpg --> |
|
|
⚫ |
] |
|
</gallery> |
|
|
⚫ |
] |
| ⚫ |
==References== |
|
|
⚫ |
] |
|
{{Reflist}}<!--added above External links/Sources by script-assisted edit--> |
|
|
|
] |
|
|
|
|
|
] |
|
==External links== |
|
|
* from ]'s Russian issue |
|
|
* from Cyclingnews |
|
|
|
|
|
{{}} |
|
|
{{Psychostimulants, agents used for ADHD and nootropics}} |
|
|
|
|
| ⚫ |
] |
|
| ⚫ |
] |
|
|
] |
|
] |
| ⚫ |
] |
|
| ⚫ |
] |
|
| ⚫ |
] |
|
|
|
|
|
|
|
{{anticonvulsant-stub}} |
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|