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Bupivacaine

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Identification
Molecular formula
C18H28N2O
CAS number
38396-39-3
IUPAC name
N-[1-[(3S,5S,8R,9S,10S,13S,14S)-3-(dimethylamino)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-N-methyl-acetamide
State
State

At room temperature, Bupivacaine is found as a solid.

Melting point (Celsius)
107.00
Melting point (Kelvin)
380.15
Boiling point (Celsius)
387.06
Boiling point (Kelvin)
660.21
General information
Molecular weight
288.44g/mol
Molar mass
288.4390g/mol
Density
0.9910g/cm3
Appearence

Bupivacaine typically appears as a white or almost white crystalline powder.

Comment on solubility

Solubility of N-[1-[(3S,5S,8R,9S,10S,13S,14S)-3-(dimethylamino)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-N-methyl-acetamide

The solubility of N-[1-[(3S,5S,8R,9S,10S,13S,14S)-3-(dimethylamino)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-N-methyl-acetamide is influenced by several factors, primarily its complex structure and the presence of functional groups.

Key points regarding its solubility include:

  • Polarity: The presence of the dimethylamino group and the acetamide moiety introduces polar characteristics, which may enhance solubility in polar solvents.
  • Hydrophobic regions: The extensive hydrophobic hydrocarbon framework may limit its solubility in water but improve solubility in organic solvents like ethanol or dimethyl sulfoxide (DMSO).
  • Temperature dependence: As with many organic compounds, solubility can increase with temperature, making warm solvent conditions potentially more favorable for dissolution.
  • Possible forms: This compound may exist in various forms depending on the solvent and conditions, which can further influence solubility profiles.

This complex interplay of polar and non-polar interactions suggests that while the compound may have limited water solubility, it likely demonstrates good solubility in organic solvents, providing versatility for various applications.

Interesting facts

Interesting Facts about N-[1-[(3S,5S,8R,9S,10S,13S,14S)-3-(dimethylamino)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-N-methyl-acetamide

This complex compound, often referred to in its abbreviated form, is a fascinating example of synthetic organic chemistry. Its molecular structure exhibits rich stereochemistry, reflecting a specific three-dimensional arrangement that can significantly influence its biological activity.

Key Facts:

  • Stereochemistry: The stereocenters indicated by the (3S,5S,8R,9S,10S,13S,14S) notation reveal that this compound has multiple chiral centers, contributing to its unique properties and potential target selectivity in medicinal chemistry.
  • Biological Activity: Compounds similar to this structure have been studied for their interactions with hormonal pathways, suggesting potential applications in endocrine therapies.
  • Dimethylaminogroup: The presence of a dimethylamino group in this structure is significant, as it often plays a role in the compound's pharmacological profile, enhancing solubility and bioavailability.
  • Complexity of Synthesis: The synthesis of such a compound typically requires advanced techniques in organic synthesis, including multi-step reactions and careful control of reaction conditions to maintain stereochemical integrity.

Due to its complexity, studying this compound can provide rich insight into the fields of medicinal chemistry and pharmacology, particularly in exploring structure-activity relationships. As the renowned chemist Marie Curie once said, "Nothing in life is to be feared; it is only to be understood". This sentiment applies beautifully here, where understanding such compounds can lead to groundbreaking advancements in drug development and therapeutic applications.

Synonyms
EPIPACHYSAMINE A
2309-42-4
Epipachysamine-A
N-[1-[(3S,5S,8R,9S,10S,13S,14S)-3-(dimethylamino)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-N-methylacetamide
Acetamide, N-(3-beta-(dimethylamino)-5-alpha-pregnan-20-alpha-yl)-N-methyl-
N-(1-((3S,5S,8R,9S,10S,13S,14S)-3-(dimethylamino)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)ethyl)-N-methylacetamide
DTXSID00945765
NS00094289
N-[3-(Dimethylamino)pregnan-20-yl]-N-methylacetamide