Desmethyl Lacosamide

Basic Information

View in Editor

CAS Number

175481-38-6

Molecular Formula

C12H16N2O3

Molecular Weight

236.27 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

138-140°C

SMILES

View in Editor

CC(=O)NC(CO)C(=O)NCC1=CC=CC=C1

InChI

InChI=1S/C12H16N2O3/c1-9(16)14-11(8-15)12(17)13-7-10-5-3-2-4-6-10/h2-6,11,15H,7-8H2,1H3,(H,13,17)(H,14,16)/t11-/m1/s1

InChIKey

XRKSCJLQKGLSKU-LLVKDONJSA-N

LogP

-0.2002000000000006

Topological Polar Surface Area

78.43 Å²

Hydrogen Bond Donor/Acceptor

3 / 5

Complexity

263

Synonyms & References

English

Desmethyl Lacosamide
LogP
N-Acetyl-D-Serine Benzyl AMide
(2R)-2-(AcetylaMino)-3-hydroxy-N-(phenylMethyl)propanaMide
Propanamide, 2-(acetylamino)-3-hydroxy-N-(phenylmethyl)-, (2R)-
UNII-PNH5357R26
XRKSCJLQKGLSKU-LLVKDONJSA-N
(R)-2-acetamido-N-benzyl-3-hydroxypropanamide
LACOSAMIDE IMPURITY F [EP IMPURITY]
o-Desmethyl lacosamide
175481-38-6
Propanamide, 2-(acetylamino)-3-hydroxy-N-(phenylmethyl)-, (R)-; (2R)-2-(Acetylamino)-3-hydroxy-N-(phenylmethyl)propanamide; (R)-N-Benzyl-2-acetamido-3-hydroxypropionamide; (2R)-2-(Acetylamino)-N-benzyl-3-hydroxypropanamide; Desmethyl Lacosamide; Lacosamide Imp. F (Pharmeuropa)
(R)-N-benzyl-2-acetamido-3-hydroxypropionamide
(R)-2-Acetamido-N-benzyl-3-hydroxypropionamide
AKOS030241147
Q27286652
SPM 12809
DTXSID401248336
SCHEMBL47275
PNH5357R26
CHEBI:173695
LACOSAMIDE METABOLITE M1
O-Desmethyl-lacosamide
(R)-2-acetamido-N-benzyl-3-hydroxy-propionamide
O-Desmethyllacosamide
CHEMBL293954
(2R)-2-(Acetylamino)-3-hydroxy-N-(phenylmethyl)propanamide
(2R)-2-acetamido-N-benzyl-3-hydroxypropanamide
N-benzyl-N2-acetyl-D-serinamide

MDL Number

MFCD18382268

FAQ

What are the physical and chemical properties of Desmethyl Lacosamide (CAS: 175481-38-6)?

Desmethyl Lacosamide is a crystalline white solid with a molecular weight of approximately 245.25 g/mol. It has a solubility of 0.2 mg/mL in water and is practically insoluble in ethanol. Desmethyl Lacosamide is relatively stable under normal conditions but can undergo hydrolysis in aqueous solutions. It is used as an anti-epileptic drug.

How is Desmethyl Lacosamide (CAS: 175481-38-6) typically synthesized?

Desmethyl Lacosamide is typically synthesized through a series of reactions including amide formation, reduction, and desulfurization. The key steps involve the use of a catalytic hydrogenation process to reduce the amide functionality and then a desulfurization step to remove the sulfur atom, followed by desmethylating the compound. This process yields a final product with a purity of over 99%.

What industries use Desmethyl Lacosamide (CAS: 175481-38-6)?

Desmethyl Lacosamide is primarily used in the pharmaceutical industry for its anti-epileptic properties. It is also used in the development of novel drugs and as a research tool in the study of sodium channels.

What precautions should be taken when handling Desmethyl Lacosamide (CAS: 175481-38-6)?

When handling Desmethyl Lacosamide, it is important to wear appropriate personal protective equipment (PPE) such as gloves and safety goggles. It should be stored in a cool, dry place away from direct sunlight. In case of spillage, it should be cleaned up according to standard procedures and the material safety data sheet (MSDS) should be consulted for specific instructions. Always ensure proper ventilation and use a fume hood when handling the compound.