Levopropylhexedrine

Last updated
Levopropylhexedrine
Levopropylhexedrine.png
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 InfoCard 100.025.678 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H21N
Molar mass 155.285 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.

Contents

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 Synthesis of levopropylhexedrine.svg
Selective synthesis of levopropylhexedrine

See also

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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.