Amfetaminil: Difference between revisions
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* (''R'')-2-[(''S'')-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-10-4) |
* (''R'')-2-[(''S'')-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-10-4) |
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* (''S'')-2-[(''R'')-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-14-2) |
* (''S'')-2-[(''R'')-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-14-2) |
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==Synthesis== |
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[[File:Amphetaminil synthesis.svg|thumb|center|700px|Amphetaminil synthesis:<ref>{{Cite DOI|10.1002/prac.19630200509}}</ref> J. Klosa, {{Cite patent|DE|1112987}} (1959); Chem. Abstr., 56: 3409d (1962).]] |
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It is synthesized by forming the Schiff's base of amphetamine with benzaldehyde, and then nucleophilic attack on the latter with cyanide anion. |
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== References == |
== References == |
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{{Reflist}} |
{{Reflist}} |
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Revision as of 16:18, 7 May 2015
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| ECHA InfoCard | 100.037.767 |
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| Formula | C17H18N2 |
| Molar mass | 250.338 g·mol−1 |
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Amphetaminil (Aponeuron, AN-1) is a stimulant drug derived from amphetamine, which was developed in the 1970s and used for the treatment of obesity,[1] ADHD,[2][3] and narcolepsy.[4] It has largely been withdrawn from clinical use following problems with abuse.[5]
Stereochemistry
Amphetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist:
- (R)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-08-4)
- (S)-2-[(S)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-12-0)
- (R)-2-[(S)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-10-4)
- (S)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-14-2)
References
- ^ Harris LS. The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology. Drug and Alcohol Dependence 1986; 17:107.
- ^ Meyer-Probst B, Vehreschild T. Influencing the lack of concentration in hyperkinetic schoolchildren with Aponeuron. Psychiatrie, Neurologie und Medizinische Psychologie (Leipz) 1976; 28:491.
- ^ Paclt I, Florian J, Brunclikova J, Ruzickova I. Effect of Aponeuron in the treatment of children with hyperkinetic syndrome. (Czech). Ceska a Slovenska Psychiatrie. 1996 May;92 Suppl 1:41-57.
- ^ Schlesser JL. Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US. MEDEX Books, Detroit, 1991.
- ^ Winter E. Drug abuse and dependence of the amphetamine type with special regard to Amphetaminil (Aponeuron(R)). (German). Psychiatrie, Neurologie und Medizinische Psychologie (Leipzig). 1976 Sep;28(9):513-25.