An internal standard for the quantification of sumatriptan
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Unlabeled Version(s)
14600Sumatriptan (succinate)
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Sumatriptan-d6 (succinate)

Item No. 28202

Technical Information
Formal Name
3-[2-[di(methyl-d3)amino]ethyl]-N-methyl-1H-indole-5-methanesulfonamide, butanedioic acid (2:1)
CAS Number
1397195-80-0
Molecular Formula
C14H15D6N3O2S • 1/2C4H6O4
Formula Weight
Purity
≥99% deuterated forms (d1-d6)
Formulation
A solid
SMILES
O=C(CCC(O)=O)O.CNS(CC1=CC=C(NC=C2CCN(C([2H])([2H])[2H])C([2H])([2H])[2H])C2=C1)(=O)=O.CNS(CC3=CC=C(NC=C4CCN(C([2H])([2H])[2H])C([2H])([2H])[2H])C4=C3)(=O)=O
InChi Code
InChI=1S/2C14H21N3O2S.C4H6O4/c2*1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3;5-3(6)1-2-4(7)8/h2*4-5,8-9,15-16H,6-7,10H2,1-3H3;1-2H2,(H,5,6)(H,7,8)/i2*2D3,3D3;
InChi Key
HIMZTGQXEPNRFN-LXRVQIONSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    Product Description

    Sumatriptan-d6 is intended for use as an internal standard for the quantification of sumatriptan (Item No. 14600) by GC- or LC-MS. Sumatriptan is an agonist of the serotonin (5-HT) receptor subtypes 5-HT1B and 5-HT1D (IC50s = 9.3 and 7.3 nM, respectively).1 It also binds to the 5-HT1F receptor (IC50 = 17.8 nM). It induces vasoconstriction in isolated human middle meningeal arteries (EC50 = 89.9 nM), an effect that can be reduced by the 5-HT1B/1D receptor antagonists GR125743 and GR127935 (Item No. 29651). Sumatriptan reduces acute, but not chronic, mechanical hyperalgesia in a mouse model of pain induced by nitroglycerin, which is a known migraine trigger in humans.2 Formulations containing sumatriptan have been used in the treatment of migraine headache.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Razzaque, Z., Heald, M.A., Pickard, J.D., et alVasoconstriction in human isolated middle meningeal arteries: Determining the contribution of 5-HT1B- and 5-HT1F-receptor activation. Br. J. Pharmacol. 47(1), 75-82 (1999).

    2. Pradhan, A., Smith, M.L., McGuire, B., et alCharacterization of a novel model of chronic migraine. Pain 155(2), 269-274 (2014).