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
Molecular Weight
288.44g/mol
Melting Point
(Celsius)
Boiling Point
(Celsius)
Density
0.9910g/cm3
Synonyms
EPIPACHYSAMINE A
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.

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