Sumatriptan

C₁₄H₂₁N₃O₂SCAS 103628-46-2295.40 g/mol

Open in Covalent MOL file

Sulfonamide Tertiary amine

Properties

Molecular formula: C₁₄H₂₁N₃O₂S
Molar mass: 295.40 g/mol
Exact mass: 295.1354 Da
Melting point: 169–171 °C
pKa: 9.5
logP: 1.32Crippen estimate
Polar surface area: 65.2 Å²
H-bond donors / acceptors: 2 / 3
Rotatable bonds: 6

Hazards

Warning

H319 Causes serious eye irritation33.3% of notifiers
H361 Suspected of damaging fertility or the unborn child50% of notifiers
H361d Suspected of damaging the unborn child16.7% of notifiers
H412 Harmful to aquatic life with long lasting effects83.3% of notifiers

Aggregated from 6 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P203, P264+P265, P273, P280, P305+P351+P338, P318, P337+P317, P405, P501

Identifiers

CAS number

103628-46-2

SMILES

CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1

InChIKey

KQKPFRSPSRPDEB-UHFFFAOYSA-N

InChI

InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

9 names

1H-Indole-5-methanesulfonamide, 3-[2-(dimethylamino)ethyl]-N-methyl-
3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide
GR 43175X
GR 43175
Zelrix
3-[2-(Dimethylamino)ethyl]-N-methylindolyl-5-methanesulfonamide
Onzetra xsail
Zecuity
1-[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide

Work with Sumatriptan

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Sumatriptan succinate103628-48-4Salt

Similar compounds

3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide88919-22-671 % similar Almotriptan154323-57-665 % similar 5-Methoxy-N,N-dimethyltryptamine1019-45-051 % similar Naratriptan121679-13-851 % similar Rizatriptan144034-80-050 % similar N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide hydrochloride143388-64-148 % similar Almotriptan malate181183-52-848 % similar Zolmitriptan139264-17-846 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Elsewhere

PubChem CAS Common Chemistry NIST WebBook