Nicotredole

Uses

Nicotredole (Tryptamide) is an orally active anti-inflammatory and analgesic agent. Nicotredole exhibits evident antiinflammatory effects of potency comparable with Phenylbutazone. Nicotredole has only weak ulcerogenic activity[1][2][3].

Biological Activity

Nicotredole (Tryptamide) is an orally active anti-inflammatory analgesic. It showed significant anti-inflammatory effects comparable to Phenylbutazone.

Synthesis

59-67-6

61-54-1

29876-14-0

GENERAL STEPS: To a solution of nicotinic acid (0.5 mmol), triethylamine (1.2 mmol), HOBT (0.6 mmol) and EDCI (0.6 mmol) in dichloromethane (8 mL) was added tryptamine (0.5 mmol). The reaction mixture was stirred at room temperature overnight, followed by evaporation under reduced pressure to remove the dichloromethane. The residue was dissolved in ethyl acetate (10 mL) and washed sequentially with 10% aqueous sodium bicarbonate (3 x 10 mL) and water (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using a solvent mixture of dichloromethane/methanol as eluent to give the pure solid product N-(2-(1H-indol-3-yl)ethyl)nicotinamide (4a). White solid; 72% yield; 1H NMR (500 MHz, DMSO-d6) δ 10.84 (s, 1H), 9.02 (d, J = 1.3 Hz, 1H), 8.82 (t, J = 5.0 Hz, 1H), 8.72 (dd, J = 4.6, 1.3 Hz, 1H), 8.20 (d, J = 7.9 Hz, 1H), 7.60 (d, J = 7.8 Hz, 1H), 7.52 (dd, J = 7.6, 5.1 Hz, 1H), 7.37 (d, J = 8.1 Hz, 1H), 7.21 (s, 1H), 7.09 (t, J = 7.5 Hz, 1H), 7.00 (t, J = 7.4 Hz, 1H), 3.59 (dd, J = 13.6, 6.9 Hz, 2H ), 3.00 (t, J = 7.4 Hz, 2H).

in vitro

in vivo

References

[1] Herman ZS, et, al. Basic pharmacological properties of a novel antiinflammatory drug tryptamide. Pol J Pharmacol Pharm. Nov-Dec 1987;39(6):729-36. PMID:2972998
[2] Szumio H. Pharmacokinetics of tryptamide following oral and intraperitoneal administration in rats. Acta Pol Pharm. 1990;47(1-2):19-22. PMID:12959253
[3] Kulig D, et, al. A comparison of anti-inflammatory, analgesic and ulcerogenic action of tryptamide, ibuprofen and piroxicam. Pol J Pharmacol Pharm. Nov-Dec 1987;39(6):769-72. PMID:2973002