1H-Indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1)

Naratriptan hydrochloride is a selective 5-HT1 receptor subtype agonist and is a triptan drug that is used for the treatment of migraine headaches.Target: 5-HT1 ReceptorNaratriptan is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. Naratriptan is available in 2.5 mg tablets. It is a selective 5-HT1 receptor subtype agonist. Naratriptan is used for the treatment of the acute migraine attacks and the symptoms of migraine, including severe, th

Naratriptan Hydrochloride is the hydrochloride salt form of naratriptan, a sulfonamide with selective serotonin (5-HT) 1 receptor agonistic activity and anti-migraine property. Naratriptan hydrochloride binds selectively and with high affinity to the 5-HT1D and 5-HT1B receptor subtypes. Activation of these 5-HT1D/B receptors located on intracranial blood vessels leads to vasoconstriction and provides relief of migraine headaches. Naratriptan hydrochloride may also exerts its effect by stimulation of 5-HT1D/1B receptors on sensory nerve endings in the trigeminal system thereby decreasing the release of pro-inflammatory neuropeptides.

Preparation of Naratriptan hydrochloride (I) :-; The compound (VIII) (50 g, 1501 mmol) was dissolved in mixture of methanol: acetic acid (0.2 lit:0.2 lit) and 2.5 g platinum oxide was added. The mixture was hydrogenated using 5kg/cmPreparation of naratriptan hydrochloride; Naratriptan (50g, 0.14mol) was dissolved in ethanol (500ml).The clear solution was acidified with ethanolic-hydrochloride to a pη of 1.0-1.5 at 25-30°C under nitrogen atmosphere. The reaction mass was further stirred for 60 minutes at 0-5°C, filtered, washed with ethanol and dried to obtain 52.5g of naratriptan hydrochloride ( yield 95.4percent) having purity of 99.77percent by ηPLC. Naratriptan (50g) was dissolved in a mixture of methanol and ethanol (1:9) at 600C till clear solution was obtained. Thereafter, pH of the reaction mixture was adjusted to 1.0 with ethanolic hydrogen chloride at 25C. The reaction mixture was cooled to 5 0C and stirred for 1 hour at same temperature. The solid thus precipitated was filtered and recrystallized from water (300ml). The resulting product was filtered, washed with ethanol to 80.8g (71.7percent) of the tile compound having purity 99.95percent by HPLC.

laxative

Molecular Weight:371.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:371.1434259
Monoisotopic Mass:371.1434259
Topological Polar Surface Area:73.6
Heavy Atom Count:24
Complexity:483
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes