Fencamfamin

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Fencamfamin
Clinical data
Pregnancy
category
  • ?
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life16 hours[2]
Identifiers
  • N-Ethyl-3-phenyl-norbornan-2-amine
JSmol)
  • CCNC1C(C2CCC1C2)C3=CC=CC=C3
  • InChI=1S/C15H21N/c1-2-16-15-13-9-8-12(10-13)14(15)11-6-4-3-5-7-11/h3-7,12-16H,2,8-10H2,1H3 checkY
  • Key:IKFBPFGUINLYQI-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Fencamfamin (INN), also known as fencamfamine or by the brand names Glucoenergan and Reactivan, is a stimulant which was developed by Merck in the 1960s.[3]

Medical uses

Fencamfamin is still used, though rarely, for treating depressive day-time fatigue, lack of concentration and lethargy, particularly in individuals who have chronic medical conditions, as its favourable safety profile makes it the most suitable drug in some cases.[4]

Adverse effects

Fencamfamin is well tolerated and causes minimal circulatory effects. Extended use may result in a dryness of the mouth.[4]

Contraindications

Not to be used with heart diseases, angina pectoris and decompensated cardiac insufficiency, glaucoma, hyper-excitability and thyrotoxicosis or while treated with monoamine oxidase inhibitors.[4]

Overdose

Symptoms of overdose are nausea, agitation and restlessness, dryness of the mouth, dizziness and tremor. In gross overdosage also associated with dyspnoea, tachycardia, disorientation and convulsions.[4]

Research

In a study on slices of rat corpus striatum and substantia nigra fencamfamin acted as an indirect dopamine agonist. It released dopamine by a similar mechanism to amphetamines, but was ten times less potent than dexamphetamine at producing this effect. The main mechanism of action was instead inhibition of dopamine reuptake. Also unlike amphetamines, fencamfamin does not inhibit the action of monoamine oxidase enzymes. It was concluded that, at least in the models employed, the in vitro profile of fencamfamin is more similar to that of nomifensine, a reportedly pure uptake inhibitor, than to d-amphetamine.[5]

In animal experiments on

SCH 23390 and by raclopride, has been seen in a study on rats with drinking water. Animals treated with naloxone before the conditioning sessions showed a place aversion instead of the place preference found in saline-treated animals. Naloxone also reduced drinking. It was proposed that naloxone induced a state of frustrative nonreward. It was suggested that both dopamine and (endogenous) opioids are important for water-induced reinforcement. Possible interactions between these two neurotransmitter systems were discussed.[7]

Synthesis

Preparation of fencamfamin precursor

Fencamfamin may be synthesized in a straightforward fashion via the

norcamphane derivative. Finally, the amino-group
is ethylated.

Although β-nitrostyrene is commercially available, it is also very easily prepared using the

Henry Reaction between benzaldehyde and nitromethane.[8]

The Diels-Alder reaction of β-nitrostyrene and cyclopentadiene is described in a number of early papers.[9][10]

The reduction of the

catalyst like Ni or Pt, while the nitro group is reduced to the amine with a metal/acid combination, such as Fe/HCl.[10] The reduction of both functional groups can also be achieved simultaneously by the use of Raney nickel,[10] and this transformation has recently been optimized by Russian chemists.[11]

Originally achieved under reductive amination conditions involving the reaction of the amine with acetaldehyde in the presence of Pt, ethylation of the amino-group has been improved by the use of Ra-Ni and ethanol.[11]

The

saturated un-ethylated amine derived from it.[13] Novakov and co-workers, citing a thesis study,[14] report that the corresponding ratio of endo-N-ethyl/exo-Φ : exo-N-ethyl/endo-Φ enantiomeric pairs is ~9:1 in fencamfamin itself.[11]

See also

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. PMID 7236868
    .
  3. ^ DE patent 1110159, "Improvements in or relating to Amino-Norcamphane Compounds", issued 1961-07-06, assigned to Merck 
  4. ^ a b c d "REACTIVAN Tablets; REACTIVAN Syrup". Merck. Archived from the original on 2020-09-25. Retrieved 2007-01-23.
  5. PMID 6136281
    .
  6. S2CID 9034041
    .
  7. S2CID 43900354
    .
  8. doi:10.15227/orgsyn.009.0066
    ; Collected Volumes, vol. 1, p. 413.
  9. doi:10.1021/ja01871a501
    .
  10. ^
    doi:10.1021/ja01155a013
    .
  11. ^
    S2CID 28946797
    .
  12. doi:10.1021/jo01070a540
    .
  13. doi:10.1021/jo01070a029
    .
  14. ^ Vollberg G (1992). Dissertation (Ph.D. thesis). Rheinische Friedrich-Wilhelms-Universität Bonn.
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