Welcome to the BenchChem Online Store!
molecular formula C14H21N3O2S B127528 Sumatriptan CAS No. 103628-46-2

Sumatriptan

Cat. No. B127528
M. Wt: 295.40 g/mol
InChI Key: KQKPFRSPSRPDEB-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
In Stock
  • Click on QUICK INQUIRY to receive a quote from our team of experts.
  • With the quality product at a COMPETITIVE price, you can focus more on your research.
Patent
US06255502B1

Procedure details

Sumatriptan caprate and hydroxypropyl-beta cyclodextrin (HPB) were complexed by the kneading method. Sumatriptan caprate (1.254 g) and HPB (3.748 g) were blended together. Water (4.5 mL) was added and the mixture ground together in a mortar with a pestle to form a uniform paste. Grinding was continued for 30 minutes. The paste was then dried in a vacuum oven (40° C.; 0 bar) for 48 hours. The solid mass was broken up, passed through a 60 mesh screen and returned to the vacuum oven (40° C.; 0 bar) for 12 hours in order to ensure uniform drying of the complex. Analysis by HPLC for sumatriptan base content, and Karl Fischer for moisture content gave the following results: % sumatriptan base was 16.40% and the moisture content was 3.45%. The complex was characterised by DSC, FT-IR and XRD.
Name
Sumatriptan caprate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
hydroxypropyl-beta cyclodextrin
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Sumatriptan caprate
Quantity
1.254 g
Type
reactant
Reaction Step Three
Name
HPB
Quantity
3.748 g
Type
reactant
Reaction Step Four
Name
Quantity
4.5 mL
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].[O-]C(CCCCCCCCC)=O.CC(O)COC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8COCC(O)C)O[C@@H]7COCC(O)C)O[C@@H]6COCC(O)C)O[C@@H]5COCC(O)C)O[C@@H]4COCC(O)C)O[C@@H]3COCC(O)C>O>[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4] |f:0.1|

Inputs

Step One
Name
Sumatriptan caprate
Quantity
0 (± 1) mol
Type
reactant
Smiles
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C.[O-]C(=O)CCCCCCCCC
Step Two
Name
hydroxypropyl-beta cyclodextrin
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(COC[C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@H](O2)[C@@H]([C@H]8O)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)O)O)O
Step Three
Name
Sumatriptan caprate
Quantity
1.254 g
Type
reactant
Smiles
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C.[O-]C(=O)CCCCCCCCC
Step Four
Name
HPB
Quantity
3.748 g
Type
reactant
Smiles
CC(COC[C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@H](O2)[C@@H]([C@H]8O)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)O)O)O
Step Five
Name
Quantity
4.5 mL
Type
solvent
Smiles
O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
the mixture ground together in a mortar with a pestle to form a uniform paste
CUSTOM
Type
CUSTOM
Details
Grinding
CUSTOM
Type
CUSTOM
Details
The paste was then dried in a vacuum oven (40° C.; 0 bar) for 48 hours
Duration
48 h
WAIT
Type
WAIT
Details
returned to the vacuum oven (40° C.; 0 bar) for 12 hours in order
Duration
12 h
CUSTOM
Type
CUSTOM
Details
to ensure uniform drying of the complex

Outcomes

Product
Details
Reaction Time
30 min
Name
Type
product
Smiles
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
© Copyright 2024 BenchChem. All Rights Reserved.