Tifluadom

Structural formula
General
Non-proprietary name	Tifluadom
other names	N - {[5- (2-fluorophenyl) -1-methyl-2,3-dihydro-1,4-benzodiazepin-2-yl] methyl} thiophene-3-carboxamide ( IUPAC ); 1-methyl-2- (3-thienylcarbonyl) aminomethyl-5- (2-fluorophenyl) - H -2,3-dihydro-1,4-benzodiazepine ( MeSH );
Molecular formula	C 22 H 20 FN 3 OS
External identifiers / databases
EC number	280-380-4
ECHA InfoCard	100,073,052
PubChem	115208
Wikidata	Q7801294
Drug information
Drug class	Benzodiazepine
Mechanism of action	Binding to the κ-opioid receptor
properties
Molar mass	393.48 g · mol -1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tifluadom is a benzodiazepine derivative that is not used therapeutically and has an abnormal mechanism of action for this class of substances.

Mechanism of action

In contrast to other benzodiazepines, Tifluadom has no effect on the GABA _A receptor and therefore does not develop the anxiolytic , sedating , hypnotic and central muscle relaxing effects typical for this group of substances . The benzodiazepine skeleton was changed through appropriate substitutions in such a way that the substance has a high affinity for the κ receptor , which results in an opioid-like effect: In animal experiments, trifluadoma shows a high analgesic potential , causes increased diuresis and stimulates the appetite and has sedating effects. It also acts as a peripheral cholecystokinin receptor antagonist.

use

Due to the undesirable effects (see below), Tifluadom is not currently used as a drug, but it is used in research.

Side effects

Due to the κ-agonism, Tifluadom shows unpleasant side effects such as dysphoria and hallucinations , comparable to the drug pentazocine ( Fortral ) , which was withdrawn from the market in 2006, and salvinorin A , which is also classified as an anesthetic and occurs in Aztec sage and has psychoactive effects. The dependency potential of Tifluadom, however, is said to be only slightly pronounced.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ D. Romer, HH Buscher, RC Hill, R. Maurer, TJ Petcher, H. Zeugner, W. Benson, E. Finner, W. Milkowski, PW Thies: Unexpected opioid activity in a known class of drug. In: Life Sciences. 20-27; 31 (12-13) 1982, pp. 1217-1220.
↑ RF Genovese, LA Dykstra: Tifluadom's effects under electric shock titration and tail-immersion procedures in squirrel monkeys. In: Life Sciences. 10; 39 (19), 1986, pp. 1713-1719.
↑ JD Leander: Kappa opioid agonists and antagonists: effects on drinking and urinary output. In: Appetite. 5 (1), 1984, pp. 7-14.
↑ HC Jackson, RD Sewell: The role of opioid receptor sub-types in tifluadom-induced feeding. In: Journal of Pharmacy and Pharmacology. 36 (10), 1984, pp. 683-686.
↑ LA Dykstra, DE Gmerek, G. Winger, JH Woods: Kappa opioids in rhesus monkeys. I. Diuresis, sedation, analgesia and discriminative stimulus effects. In: Journal of Pharmacology and Experimental Therapeutics. 242 (2), 1987, pp. 413-420.
^ SJ Cooper, WR Moores, A. Jackson, DJ Barber: Effects of tifluadom on food consumption compared with chlordiazepoxide and kappa agonists in the rat. In: Neuropharmacology. Sep 1985, PMID 2997653 .
↑ RS Chang, VJ Lotti, TB Chen, ME Keegan: Tifluadom, a kappa-opiate agonist, acts as a peripheral cholecystokinin receptor antagonist. In: Neuropharmacology. Sep 1985, PMID 3027627 .
↑ Th. Velocity: Intoxicating drugs. Market forms and modes of action. Springer, Heidelberg / Dordrecht / London / New York 2013, ISBN 978-3-642-30162-9 , p. 716 RN 3449.

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[2] D. Romer, HH Buscher, RC Hill, R. Maurer, TJ Petcher, H. Zeugner, W. Benson, E. Finner, W. Milkowski, PW Thies: Unexpected opioid activity in a known class of drug. In: Life Sciences. 20-27; 31 (12-13) 1982, pp. 1217-1220.

[3] RF Genovese, LA Dykstra: Tifluadom's effects under electric shock titration and tail-immersion procedures in squirrel monkeys. In: Life Sciences. 10; 39 (19), 1986, pp. 1713-1719.

[4] JD Leander: Kappa opioid agonists and antagonists: effects on drinking and urinary output. In: Appetite. 5 (1), 1984, pp. 7-14.

[5] HC Jackson, RD Sewell: The role of opioid receptor sub-types in tifluadom-induced feeding. In: Journal of Pharmacy and Pharmacology. 36 (10), 1984, pp. 683-686.

[6] LA Dykstra, DE Gmerek, G. Winger, JH Woods: Kappa opioids in rhesus monkeys. I. Diuresis, sedation, analgesia and discriminative stimulus effects. In: Journal of Pharmacology and Experimental Therapeutics. 242 (2), 1987, pp. 413-420.

[7] SJ Cooper, WR Moores, A. Jackson, DJ Barber: Effects of tifluadom on food consumption compared with chlordiazepoxide and kappa agonists in the rat. In: Neuropharmacology. Sep 1985, PMID 2997653 .

[8] RS Chang, VJ Lotti, TB Chen, ME Keegan: Tifluadom, a kappa-opiate agonist, acts as a peripheral cholecystokinin receptor antagonist. In: Neuropharmacology. Sep 1985, PMID 3027627 .

[9] Th. Velocity: Intoxicating drugs. Market forms and modes of action. Springer, Heidelberg / Dordrecht / London / New York 2013, ISBN 978-3-642-30162-9 , p. 716 RN 3449.