Levopropylhexedrine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (S)-1-cyclohexyl-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.025.678
Chemical and physical data
FormulaC10H21N
Molar mass155.285 g·mol−1
3D model (JSmol)
  • N([C@H](CC1CCCCC1)C)C

Levopropylhexedrine (Eventin) is an adrenergic alkylamine used as an anorectic in Germany[1][2] and patented by Smith Kline & French in 1947.[3] It has also been used in the anticonvulsant preparation barbexaclone in combination with phenobarbital to offset sedation.[4][5][6] Levopropylhexedrine is the levorotatory S-enantiomer of propylhexedrine. The dextrorotatory counterpart is known as dextropropylhexedrine.

Synthesis

The enantiopure synthesis of levopropylhexedrine may be accomplished in a two step reaction. The first step is the Wenker synthesis of the relevant aziridine. The second step is the simple catalytic hydrogenation of the propylhexedrine-aziridine.[7]

Selective synthesis of Levopropylhexedrine

See also

References

  1. ↑ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
  2. ↑ Hofer R, Locker A (1958). "Über therapeutische Erfahrungen mit dem Appetitzügler Eventin" [Therapeutic experiences with the appetite depressant eventin]. Wiener Medizinische Wochenschrift (in German). 108 (14): 304–6. PMID 13558159.
  3. ↑ US 2454746 Cyclohexylalkylamines
  4. ↑ Oliveira C, Fernandes I, De Lima JM, Musse R (1977). "Ensaio clínico com barbexaclone nas epilepsias" [Clinical trial with barbexaclone in epilepsies]. Arquivos de Neuro-Psiquiatria (in Portuguese). 35 (1): 68–72. doi:10.1590/s0004-282x1977000100008. PMID 14606.
  5. ↑ Iven H, Feldbusch E (1983). "Pharmacokinetics of phenobarbital and propylhexedrine after administration of barbexaclone in the mouse". Naunyn-Schmiedeberg's Archives of Pharmacology. 324 (2): 153–9. doi:10.1007/bf00497022. PMID 6139756. S2CID 25628466.
  6. ↑ Seyffart, G. (1991). Drug dosage in renal insufficiency. Boston: Kluwer Academic Publishers. ISBN 0-7923-0964-2.
  7. ↑ Haberl, R. (1958-11-01). "Über eine neue Bildungsweise des 1,2-Dimethyl-3-phenyl-äthylenimins". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften (in German). 89 (6): 814–816. doi:10.1007/BF00902540. ISSN 1434-4475.
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