Amfetaminil: Difference between revisions

{{Short description|Amphetamine-derived stimulant drug}}

{{cs1 config|name-list-style=vanc}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444359166

| IUPAC_name = 2-Phenyl-2-(1-phenylpropan-2-ylamino)acetonitrile

| image = Amphetaminil.svg

| image2 = Amfetaminil.png

<!--Clinical data-->

| tradename =

| routes_of_administration =

| legal_DE = Anlage II

| legal_US = Schedule IV

<!--Identifiers-->

| 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}}

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104064

<!--Chemical data-->

| C=17 | H=18 | N=2

'''Amfetaminil''' (also known as '''amphetaminil''', '''''N''-cyanobenzylamphetamine''',<ref name="MortonHall2012">{{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–}}</ref> 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]],<ref name="pmid2874966">{{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 }}</ref> [[ADHD]],<ref name="pmid1005547">{{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 }}</ref><ref name="pmid8768943">{{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 }}</ref> and [[narcolepsy]].<ref>{{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 }}</ref> It has largely been withdrawn from clinical use following problems with [[drug abuse|abuse]].<ref name="pmid1005549">{{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 }}</ref> The drug is a [[prodrug]] to [[amphetamine]].<ref name="Dasgupta2012">{{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–}}</ref><ref name="LLC2014">{{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–}}</ref>

Amfetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist:

* (''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|thumb|center|500px|Synthesis:<ref name="pmid5165569">{{cite journal | vauthors = Yashunskii VG, Gorkin VZ, Mashkovskii MD, Altshuler RA, Veryovkina IV, Kholodov LE | title = Synthesis and pharmacological effects of some alkyl-, aryl-, and aralkylsydnonimines | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 10 | pages = 1013–5 | date = October 1971 | pmid = 5165569 | doi = 10.1021/jm00292a042}}</ref><ref name="pmid1242355">{{cite journal | vauthors = Klosa J | title = [The stability of amphetaminil. Syntheses with amphetaminil (author's transl)] | language = German | journal = Arzneimittel-Forschung | volume = 25 | issue = 8 | pages = 1252–8 | date = August 1975 | pmid = 1242355 | doi = | url = }}</ref><ref name="pmid1243655">{{cite journal | vauthors = Klosa J | title = [On the crystallisation of amphetaminil base into its hydrochloride salt (author's transl)] | language = German | journal = Arzneimittel-Forschung | volume = 25 | issue = 12 | pages = 1863–4 | date = 1975 | pmid = 1243655 | doi = | url = }}</ref><ref>{{cite journal | vauthors = Beyer KH, Strassner W, Klinge D | title = Amphetaminil [α-(1-benzylethylamino)-α-phenylacetonitrile] | journal = Deutsche Apotheker Zeitung | volume = 111 | issue = 19 | pages = 677–680 }}</ref><ref>{{cite journal | vauthors = Kholodov LE | title = Sydnones and sydnonimines. XXXV. Salts and exocyclic derivatives of some sydnonimines. | journal = Zhurnal Organicheskoi Khimii | date = 1967 | volume = 3 | issue = 8 | pages = 1513–1518 }}</ref>]]

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.

{{Monoamine releasing agents}}

[[Category:Norepinephrine-dopamine releasing agents]]

[[Category:Prodrugs]]

[[Category:Substituted amphetamines]]

[[Category:Wakefulness-promoting agents]]

[[Category:World Anti-Doping Agency prohibited substances]]