Butriptyline

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Butriptyline
Butriptyline.svg
Systematic (IUPAC) name
(±)-3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-yl)-N,N,2-trimethylpropan-1-amine
Clinical data
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Half-life 20 hours
Identifiers
CAS number 35941-65-2 YesY
ATC code N06AA15
PubChem CID 21772
ChemSpider 20462 YesY
UNII Z22441975X YesY
KEGG D07601 YesY
ChEMBL CHEMBL2110816
Chemical data
Formula C21H27N 
Mol. mass 293.446 g/mol
 YesY (what is this?)  (verify)

Butriptyline (Evadene, Evadyne, Evasidol, Centrolese) is a tricyclic antidepressant (TCA) which has been used in Europe since 1974.[1][2][3][4][5] It is the isobutyl side chain homologue of amitriptyline and produces similar effects to it, but with less marked side effects like sedation and interactions with adrenergic drugs.[1][5][6]

In vitro, butriptyline is a strong antihistamine and anticholinergic, moderate 5-HT2 and α1-adrenergic receptor antagonist, and weak serotonin reuptake inhibitor, with negligible affinity for the norepinephrine and dopamine transporters.[7][8][9] These actions appear to confer a profile similar to that of iprindole and trimipramine with serotonin-blocking effects as the predominant mediator of mood-lifting efficacy.[10][11][12]

However, in clinical trials, using similar doses, butriptyline was found to be even more effective than amitriptyline as an antidepressant, despite the fact that amitriptyline is much, much stronger as both a 5-HT2 antagonist and serotonin-norepinephrine reuptake inhibitor.[7][8][9][13] As a result, it can be inferred that butriptyline, in vivo, may function as a prodrug to a metabolite with more appreciable pharmacodynamics.

See also[edit]

References[edit]

  1. ^ a b José Miguel Vela; Helmut Buschmann; Jörg Holenz; Antonio Párraga; Antoni Torrens (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. p. 180. ISBN 3-527-31058-4. 
  2. ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0. 
  3. ^ Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. p. 213. ISBN 0-8155-1144-2. 
  4. ^ Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 1157. ISBN 0-412-54090-8. 
  5. ^ a b Paykel, Eugene S. (1992). Handbook of affective disorders. New York: Guilford Press. p. 339. ISBN 0-89862-674-9. 
  6. ^ Aronson, Jeffrey Kenneth (2008). Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. ISBN 0-444-53266-8. 
  7. ^ a b Richelson E, Nelson A (July 1984). "Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro". The Journal of Pharmacology and Experimental Therapeutics 230 (1): 94–102. PMID 6086881. 
  8. ^ a b Wander TJ, Nelson A, Okazaki H, Richelson E (December 1986). "Antagonism by antidepressants of serotonin S1 and S2 receptors of normal human brain in vitro". European Journal of Pharmacology 132 (2-3): 115–21. doi:10.1016/0014-2999(86)90596-0. PMID 3816971. 
  9. ^ a b Tatsumi M, Groshan K, Blakely RD, Richelson E (December 1997). "Pharmacological profile of antidepressants and related compounds at human monoamine transporters". European Journal of Pharmacology 340 (2-3): 249–58. doi:10.1016/S0014-2999(97)01393-9. PMID 9537821. 
  10. ^ Jaramillo J, Greenberg R (February 1975). "Comparative pharmacological studies on butriptyline and some related standard tricyclic antidepressants". Canadian Journal of Physiology and Pharmacology 53 (1): 104–12. doi:10.1139/y75-014. PMID 166748. 
  11. ^ Randrup A, Braestrup C (August 1977). "Uptake inhibition of biogenic amines by newer antidepressant drugs: relevance to the dopamine hypothesis of depression". Psychopharmacology 53 (3): 309–14. doi:10.1007/BF00492370. PMID 408861. 
  12. ^ Richelson E, Pfenning M (September 1984). "Blockade by antidepressants and related compounds of biogenic amine uptake into rat brain synaptosomes: most antidepressants selectively block norepinephrine uptake". European Journal of Pharmacology 104 (3-4): 277–86. doi:10.1016/0014-2999(84)90403-5. PMID 6499924. 
  13. ^ Guelfi JD, Dreyfus JF, Delcros M, Pichot P (1983). "A double-blind controlled multicenter trial comparing butriptyline with amitriptyline". Neuropsychobiology 9 (2-3): 142–6. doi:10.1159/000117952. PMID 6353270.