amfetaminil
{{Short description|Amphetamine-derived stimulant drug}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444359166
| IUPAC_name = 2-Phenyl-2-(1-phenylpropan-2-ylamino)acetonitrile
| image = Amphetaminil.svg
| image_class = skin-invert-image
| image2 = Amfetaminil.png
| image_class2 = bg-transparent
| tradename =
| routes_of_administration =
| legal_DE = Anlage II
| legal_US = Schedule IV
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 17590-01-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0XU0V77JVE
| ATC_prefix = none
| PubChem = 28615
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26613
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104064
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07446
| C=17 | H=18 | N=2
| smiles = N#CC(NC(C)Cc1ccccc1)c2ccccc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H18N2/c1-14(12-15-8-4-2-5-9-15)19-17(13-18)16-10-6-3-7-11-16/h2-11,14,17,19H,12H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NFHVTCJKAHYEQN-UHFFFAOYSA-N
}}
Amfetaminil (also known as amphetaminil, N-cyanobenzylamphetamine,{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA13|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=13–}} and AN-1; brand name Aponeuron) is a stimulant drug derived from amphetamine, which was developed in the 1970s and used for the treatment of obesity,{{cite journal | vauthors = Harris LS | title = The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology | journal = Drug and Alcohol Dependence | volume = 17 | issue = 2–3 | pages = 107–18 | date = June 1986 | pmid = 2874966 | doi = 10.1016/0376-8716(86)90002-5 }} ADHD,{{cite journal | vauthors = Meyer-Probst B, Vehreschild T | title = [Influencing the lack of concentration in hyperkinetic school children with Aponeuron] | language = de | journal = Psychiatrie, Neurologie, und Medizinische Psychologie | volume = 28 | issue = 8 | pages = 491–9 | date = August 1976 | pmid = 1005547 }}{{cite journal | vauthors = Paclt I, Florian J, Brunclíková J, Růzicková I | title = [Effect of Aponeuron in the treatment of children with hyperkinetic syndrome] | language = cs | journal = Ceska a Slovenska Psychiatrie | volume = 92 | pages = 41–57 | date = May 1996 | issue = Suppl 1 | pmid = 8768943 }} and narcolepsy.{{cite book | vauthors = Schlesser JL | title = Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US. | publisher = MEDEX Books | location = Detroit | date = 1991 }} It has largely been withdrawn from clinical use following problems with abuse.{{cite journal | vauthors = Winter E | title = [Drug abuse and dependence of the amphetamine type with special regard to Amphetaminil (Aponeuron(R))] | language = de | journal = Psychiatrie, Neurologie, und Medizinische Psychologie | volume = 28 | issue = 9 | pages = 513–25 | date = September 1976 | pmid = 1005549 }} The drug is a prodrug to amphetamine.{{cite book| first = Amitava | last = Dasgupta |title=Resolving Erroneous Reports in Toxicology and Therapeutic Drug Monitoring: A Comprehensive Guide|url=https://books.google.com/books?id=0mD9kKcUU8UC&pg=PT96|date=2 July 2012|publisher=John Wiley & Sons|isbn=978-1-118-34785-0|pages=96–}}{{cite book|author=AHC Media, LLC|title=Pediatric Trauma Care II: A clinical reference for physicians and nurses caring for the acutely injured child|url=https://books.google.com/books?id=9fucAwAAQBAJ&pg=PA118|date=17 March 2014|publisher=AHC Media, LLC|isbn=978-1-934863-59-6|pages=118–}}
Stereochemistry
Amfetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist:
File:Amphetaminil Structural Formulae of four Stereoisomers.png
- (R)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number 478392-08-4)
- (S)-2-[(S)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number 478392-12-0)
- (R)-2-[(S)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number 478392-10-8)
- (S)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number 478392-14-2)
Synthesis
File:Amphetaminil synthesis.svg
Schiff base formation between amphetamine (1) and benzaldehyde (2) gives benzalamphetamine [2980-02-1] (3). Nucleophilic attack of cyanide anion on the imine (c.f. Strecker reaction) gives amfetaminil (4). Finally, reaction with nitrous acid gives (5). The rearrangement to a Sydnone then occurs to give [https://pubchem.ncbi.nlm.nih.gov/compound/88166659 CID:88166659] (6). Feprosidnine is sans the phenyl group.
References
{{Reflist}}
{{Stimulants}}
{{Anorectics}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
Category:Norepinephrine-dopamine releasing agents
Category:Substituted amphetamines