Naratriptan HCl (GR-85548A; GR85548A; Amerge; Naramig), the hydrochloride salt of naratriptan, is a triptan class of selective 5-HT₁ receptor subtype agonist used for the treatment of migraine headaches. was created and distributed by GSK, and tablets containing 2.5 mg are available. Naratriptan functions as a selective agonist of the 5-HT1 receptor subtype as its mode of action. Naratriptan is used to treat acute migraine attacks as well as the symptoms of migraine, which include intense, throbbing headaches that can occasionally be accompanied by light or sound sensitivity and nausea.

Physicochemical Properties

Molecular Formula	C17H26CLN3O2S
Molecular Weight	371.93
Exact Mass	371.143
Elemental Analysis	C, 54.90; H, 7.05; Cl, 9.53; N, 11.30; O, 8.60; S, 8.62
CAS #	143388-64-1
Related CAS #	Naratriptan; 121679-13-8; Naratriptan-d3 hydrochloride; 1190021-64-7
PubChem CID	60875
Appearance	White to off-white solid powder
Boiling Point	541.3ºC at760mmHg
Melting Point	234-236ºC
Flash Point	281.2ºC
Vapour Pressure	8.81E-12mmHg at 25°C
LogP	4.28
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Heavy Atom Count	24
Complexity	483
Defined Atom Stereocenter Count	0
SMILES	Cl[H].S(C([H])([H])C([H])([H])C1C([H])=C([H])C2=C(C=1[H])C(=C([H])N2[H])C1([H])C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])C1([H])[H])(N([H])C([H])([H])[H])(=O)=O
InChi Key	AWEZYKMQFAUBTD-UHFFFAOYSA-N
InChi Code	InChI=1S/C17H25N3O2S.ClH/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14;/h3-4,11-12,14,18-19H,5-10H2,1-2H3;1H
Chemical Name	N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide;hydrochloride
Synonyms	GR-85548A; Naratriptan HCl; Naratriptan Hydrochloride; GR 85548A; GR85548A; Amerge; Naramig
HS Tariff Code	2935.90.6000
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	5-HT1 Receptor
ln Vitro	In vitro activity: Naratriptan is a triptan medication that is sold by GlaxoSmithKline and is intended to treat migraine headaches. Tablets containing 2.5 mg of naraptan are obtainable. It is an agonist of the specific 5-HT1 receptor subtype. Naratriptan is used to treat acute migraine attacks as well as the symptoms of migraine, which include intense, throbbing headaches that can occasionally be accompanied by light or sound sensitivity and nausea.
ln Vivo
Animal Protocol
References	[1]. J Headache Pain.2011 Aug;12(4):399-403.
Additional Infomation	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. See also: Naratriptan (has active moiety).

Solubility Data

Solubility (In Vitro)	DMSO: ~74 mg/mL (~199.0 mM) Water: ~22 mg/mL (~59.2 mM) Ethanol: <1 mg/mL
Solubility (In Vivo)	Solubility in Formulation 1: 6.67 mg/mL (17.93 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C). Solubility in Formulation 2: 5%DMSO + 40%PEG300 + 5%Tween 80 + 50%ddH2O: 3.7mg/ml (9.95mM)  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6887 mL	13.4434 mL	26.8868 mL
	5 mM	0.5377 mL	2.6887 mL	5.3774 mL
	10 mM	0.2689 mL	1.3443 mL	2.6887 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.