Sumatriptan

Molecular structure via molpic based on CDK

Conformer []

Conformer structure via 3Dmol.js

Physical properties []
Molecular mass	295.40 g/mol ^[1]
Melting point	169-170 ^[1]
Solubility	40.3 [ug/mL] (The mean of the results at pH 7.4) ^[1]
Predicted LogP	0.9 ^[1]

Structural Identifiers []
Molecular formula	C₁₄H₂₁N₃O₂S ^[1]
IUPAC name	1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide ^[1]
SMILES	CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C ^[1]
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 ^[1]
InChIKey	KQKPFRSPSRPDEB-UHFFFAOYSA-N ^[1]

Sumatriptan

Sumatriptan (also known as Imitrex, Sumatran, Sumax, Imigran, Sumatriptanum, 3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide, 1H-Indole-5-methanesulfonamide, 3-[2-(dimethylamino)ethyl]-N-methyl-, Imigran Recovery, 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide or 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide) is a substance of the tryptamine class.

Chemistry

Stereochemistry []

Sumatriptan is a achiral mixture

Anodyne Usernotes []
0xea / Sumatriptan via	warm uncomfortable panick inducing rush and burning sensation in my head immediately upon intravenous injection; increased sweating; relaxed cool and clear head feeling

Experience reports []

There are currently 5 experience reports involving sumatriptan on OpenErowid:

External links []

References []

National Center for Biotechnology Information. PubChem Compound Summary for CID 5358, Sumatriptan. Accessed August 2, 2025. https://pubchem.ncbi.nlm.nih.gov/compound/5358