Didesmethyl sumatriptan

Basic Information

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CAS Number

88919-22-6

Molecular Formula

C12H17N3O2S

Molecular Weight

267.35 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

152-155°C

SMILES

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CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN

InChI

InChI=1S/C12H17N3O2S/c1-14-18(16,17)8-9-2-3-12-11(6-9)10(4-5-13)7-15-12/h2-3,6-7,14-15H,4-5,8,13H2,1H3

InChIKey

MURZXKIEJFJMPP-UHFFFAOYSA-N

LogP

0.7183

Topological Polar Surface Area

87.98 Å²

Hydrogen Bond Donor/Acceptor

4 / 5

Complexity

366

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide
3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide Didesmethyl Sumatriptan
3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide (Didesmethyl Sumatriptan)
1-(3-(2-Aminoethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide
1-[3-(2-aminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide
1H-Indole-5-methanesulfonamide,3-(2-aminoethyl)-N-methyl-
1-(3-(2-Aminoethyl)-1H-indol-5-yl)-N-met
1H-Indole-5-methanesulfonamide,3-(2-aminoethyl)-N-methyl
2-[5-[[(methylamino)sulphonyl]methyl]-1H-indol-3-yl]ethanamine
3-(2-aminoethyl)-1H-indole-5-yl-N-methyl methane sulphonamide
3-(2-aminoethyl)-N-methyl-1H-indole-5-methanesulphonamide
C-<3-(2-aminoethyl)-1H-indol-5-yl>-N-methylmethanesulphonamide
Didesmethyl sumatriptan
UNII-WE0Q003U63
1H-Indole-5-methanesulfonamide, 3-(2-aminoethyl)-N-methyl-
WE0Q003U63
(3-(2-Aminoethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide
[3-(2-Aminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide
3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide (ACI)
1-[3-(2-Aminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide
1-(3-(2-aminoethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide
SUMATRIPTAN IMPURITY, (3-(2-(AMINOETHYL))-1H-INDOL-5-YL)-N-METHYLMETHANESULFONAMIDE- [USP IMPURITY]
Q27292582
STL018673
SUMATRIPTAN SUCCINATE IMPURITY E [EP IMPURITY]
Sumatriptan EP Impurity E
Sumatriptan succinate impurity, (3-(2-(aminoethyl))-1H-indol-5-yl)-N-methylmethanesulfonamide- [USP]
DTXSID90237424
SCHEMBL5918470
88919-22-6
MFCD08063851

MDL Number

MFCD08063851

Customs Code

2935009090

FAQ

What are the physical and chemical properties of Didesmethyl sumatriptan (CAS: 88919-22-6)?

Didesmethyl sumatriptan is a white to off-white crystalline powder with a molecular weight of approximately 350.44 g/mol. It is sparingly soluble in water and has good solubility in organic solvents like ethanol. It is stable under normal conditions but may degrade under strong acidic or basic conditions. The compound is not highly reactive but should be handled with care to avoid potential degradation or adverse reactions.

How is Didesmethyl sumatriptan (CAS: 88919-22-6) typically synthesized?

Didesmethyl sumatriptan is usually synthesized via a multi-step process involving the reduction of sumatriptan followed by desulfurization. The key steps include the use of a hydrogenation catalyst like palladium on carbon, followed by a desulfurization step using a suitable reagent such as hydrazine. The overall yield is typically around 70-80%, with good selectivity for the desired product.

What industries use Didesmethyl sumatriptan (CAS: 88919-22-6)?

Didesmethyl sumatriptan is primarily used in the pharmaceutical industry, specifically for the development of migraine headache treatments. It is a key intermediate in the synthesis of sumatriptan, a well-known anti-migraine drug. It has limited applications in other industries such as polymers and sensors, but its primary use remains in the pharmaceutical sector.

What precautions should be taken when handling Didesmethyl sumatriptan (CAS: 88919-22-6)?

When handling Didesmethyl sumatriptan, it is important to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated fume hood to avoid inhalation of dust. Spills should be cleaned up with appropriate chemical spill kits. Always refer to the Safety Data Sheet (SDS) for detailed information on handling and storage. The compound should be stored in a cool, dry place away from direct sunlight and heat sources.