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Tifluadom

Pair of enantiomers

Pair of enantiomers

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid461743259
imageTifluadom.svg
width215px
image_classskin-invert-image
routes_of_administrationunknown
CAS_number_Ref
CAS_number83386-35-0
ATC_prefixnone
PubChem115208
IUPHAR_ligand1667
ChemSpiderID_Ref
ChemSpiderID103084
UNII_Ref
UNIITF8X866L0I
KEGG_Ref
KEGGD02694
ChEMBL_Ref
ChEMBL169703
IUPAC_name*N*-[[5-(2-Fluorophenyl)-1-methyl-2,3-dihydro-1,4-benzodiazepin-2-yl]methyl]thiophene-3-carboxamide
C22H=20F=1N=3O=1S=1
smilesO=C(NCC1N(c3ccccc3C(=N/C1)\c2ccccc2F)C)c4ccsc4
StdInChI_Ref
StdInChI1S/C22H20FN3OS/c1-26-16(13-25-22(27)15-10-11-28-14-15)12-24-21(17-6-2-4-8-19(17)23)18-7-3-5-9-20(18)26/h2-11,14,16H,12-13H2,1H3,(H,25,27)
StdInChIKey_Ref
StdInChIKeyNPGABYHTDVGGJK-UHFFFAOYSA-N

| elimination_half-life =

Tifluadom is a benzodiazepine derivative with an unusual activity profile. Unlike most benzodiazepines, tifluadom has no activity at the GABAA receptor, but instead is a selective agonist for the κ-opioid receptor. It has potent analgesic and diuretic effects in animals, and also has sedative effects and stimulates appetite.

While tifluadom has several effects which might have potential uses in medicine, such as analgesia and appetite stimulation, κ-opioid agonists tend to produce undesirable effects in humans such as dysphoria and hallucinations, and so these drugs tend to only be used in scientific research. Dysphoric effects are similar to those seen when using other κ-opioid receptor agonists like pentazocine and salvinorin A, and can be considered the opposite of morphine-induced euphoria. As such, kappa agonists are believed to have very limited abuse potential.

References

References

  1. "2-Acylaminomethyl-1,4-benzodiazepine derivatives and their salts and pharmaceutical compositions thereof".
  2. (1982). "Unexpected opioid activity in a known class of drug". Life Sciences.
  3. (November 1986). "Tifluadom's effects under electric shock titration and tail-immersion procedures in squirrel monkeys". Life Sciences.
  4. (March 1984). "Kappa opioid agonists and antagonists: effects on drinking and urinary output". Appetite.
  5. (October 1984). "The role of opioid receptor sub-types in tifluadom-induced feeding". The Journal of Pharmacy and Pharmacology.
  6. (August 1987). "Kappa opioids in rhesus monkeys. I. Diuresis, sedation, analgesia and discriminative stimulus effects.". Journal of Pharmacology and Experimental Therapeutics.
Info: Wikipedia Source

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carboxamides benzodiazepines hallucinogenic-kappa-opioid-receptor-agonists 2-fluorophenyl-compounds thiophenes
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