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SML0248

Sigma-Aldrich

Zolmitriptan

≥98% (HPLC)

Synonym(s):

(4S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone, (S)-4-((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)-2-oxazolidinone, 311C90

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About This Item

Empirical Formula (Hill Notation):
C16H21N3O2
CAS Number:
139264-17-8
Molecular Weight:
287.36
MDL number:
MFCD00871503
UNSPSC Code:
12352200
PubChem Substance ID:
329825258
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -3 to -8°, c = 1 in methanol

color

white to beige

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

CN(C)CCc1c[nH]c2ccc(C[C@H]3COC(=O)N3)cc12

InChI

1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1

InChI key

ULSDMUVEXKOYBU-ZDUSSCGKSA-N

Gene Information

human ... HTR1B(3351) , HTR1D(3352)

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Application

Zolmitriptan has been used as a 5-hydroxytryptamine receptor 1B (5-HT1B/D) activator to treat grafts to study its effects on the morphology of the ectopic eye.
Zolmitriptan has been used to induce hyper-innervation of transplants.

Biochem/physiol Actions

Zolmitriptan is a potent, selective. centrally and peripherally acting 5HT1B/1D receptor agonist.
Zolmitriptan is a selective serotonin receptor agonist of the 5HT1B and 5HT1D subtypes, both centrally and peripherally. It has been used clinically for the acute treatment of migraine attacks with or without aura and cluster headaches.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000225378
0000225378
0000137099
0000137099
022M4724V

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Ziya Bayrak et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 78(3), 499-505 (2011-03-01)
First-pass metabolism can be overcome by sublingual drug delivery, and quick drug entry into the systemic circulation can be obtained. In certain diseases such as migraine therapy, taking fast pharmacological response is an important criteria. In this study, zolmitriptan sublingual
Michal Douša et al.
Journal of pharmaceutical and biomedical analysis, 58, 1-6 (2011-10-11)
A new impurity was detected and determined using gradient ion-pair UHPLC method with UV detection in zolmitriptan (ZOL). Using MS, NMR and IR study the impurity was identified as (4S,4'S)-4,4'-(2,2'-(4-(dimethylamino)butane-1,1-diyl)bis(3-(2-(dimethylamino) ethyl)-1H-indole-5,2-diyl))bis(methylene)di(oxazolidin-2-one) (ZOL-dimer). The standard of ZOL-dimer was consequently prepared via
R B Lipton et al.
Cephalalgia : an international journal of headache, 17 Suppl 18, 53-59 (1997-12-17)
Zolmitriptan (Zomig, formerly 311C90) is a novel, oral antimigraine drug that is consistently effective and well tolerated in the acute treatment of migraine headache and its associated symptoms. The purpose of this article is to review data available from pharmacological
G R Martin
Cephalalgia : an international journal of headache, 17 Suppl 18, 4-14 (1997-12-17)
Zolmitriptan (Zomig; formerly 311C90) is a novel 5-hydroxytryptamine (5HT)1B/1D receptor agonist with proven efficacy in the acute treatment of migraine with or without preceding aura. The drug differs from presently available members of this drug class in that it combines
P Rolan
Cephalalgia : an international journal of headache, 17 Suppl 18, 21-27 (1997-12-17)
Seven randomized studies in healthy volunteers have investigated interactions between zolmitriptan (Zomig, formerly 311C90), a 5HT1B/1D agonist for acute migraine therapy, and selected drugs with which there was a possibility of interaction or a likelihood of concurrent use. Co-administration of
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