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Buprenorphine

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Identification
Molecular formula
C29H41NO4
CAS number
52485-79-7
IUPAC name
(1S,2S,6R)-5-(cyclopropylmethyl)-16-(1-hydroxy-1-methyl-ethyl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
State
State

At room temperature, buprenorphine is typically found in a solid state.

Melting point (Celsius)
216.00
Melting point (Kelvin)
489.15
Boiling point (Celsius)
580.20
Boiling point (Kelvin)
853.40
General information
Molecular weight
467.64g/mol
Molar mass
467.6410g/mol
Density
1.2652g/cm3
Appearence

Buprenorphine is usually found as a white to off-white crystalline powder. It is odorless and has a bitter taste. The powder is sparingly soluble in water but freely soluble in alcohol and ether.

Comment on solubility

Solubility of (1S,2S,6R)-5-(cyclopropylmethyl)-16-(1-hydroxy-1-methyl-ethyl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol

The solubility of (1S,2S,6R)-5-(cyclopropylmethyl)-16-(1-hydroxy-1-methyl-ethyl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol can be influenced by various factors. Due to its complex structure, we can summarize the key aspects of its solubility as follows:

  • Polarity: The presence of hydroxyl groups generally increases solubility in polar solvents like water, while hydrophobic groups tend to favor solubility in non-polar solvents.
  • Functional Groups: The methoxy group and the hydroxyl functionality introduce regions of polarity that may enhance solubility in organic solvents and diminish solubility in strong polar solvents.
  • Hydrophobic Regions: The cyclopropylmethyl moiety may reduce overall solubility in highly polar environments, as non-polar parts of the molecule become more pronounced compared to polar segments.
  • pH Sensitivity: Compounds with functional groups that can accept or donate protons may demonstrate variable solubility depending on the acidity or basicity of the solution.

In summary, predicting the solubility of compounds like (1S,2S,6R)-5-(cyclopropylmethyl)-16-(1-hydroxy-1-methyl-ethyl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol involves a careful balance of its chemical structure, the polarity of solvents, and the impact of environmental conditions. Understanding these properties assists in optimizing its application and formulation in various settings.

Interesting facts

Interesting Facts about (1S,2S,6R)-5-(Cyclopropylmethyl)-16-(1-hydroxy-1-methyl-ethyl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol

The compound detailed above is a fascinating example of a complex organic molecule featuring a rich structural framework. Here are some intriguing points about it:

  • Structural Complexity: With a hexacyclic structure, this compound showcases a remarkable arrangement of rings and functional groups, providing an excellent case study for students of organic chemistry.
  • Diverse Functional Groups: The presence of various functional groups such as hydroxyl, methoxy, and aza functionality makes it a prime candidate for examining reaction mechanisms and functional group transformations.
  • Cyclopropylmethyl Group: The inclusion of the cyclopropylmethyl substituent adds strain and unique reactivity patterns, often leading to interesting chemical behavior during synthesis.
  • Importance in Medicinal Chemistry: Compounds of this nature can serve as lead compounds in drug development, possessing potential biological activity that can be explored through further research.

Howard Johnson, a notable chemist, once stated, "The complexity of a molecule is not just a measure of its size, but also a gateway into the realms of reactivity and function." This compound exemplifies this notion perfectly. Its intricate structure underlines the often surprising and nonlinear nature of organic synthesis.

In summary, studying this compound can reveal much about the underlying principles of structural and synthetic organic chemistry, including aspects of stereochemistry and reactivity. Its exploration can yield insights not only for chemists but also for those interested in the pharmacological applications of complex organic structures.

Synonyms
[3H]-diprenorphine
CHEMBL24995
BDBM21865
PDSP2_000850
(14beta)-17-(cyclopropylmethyl)-18-(1-hydroxy-1-methylethyl)-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
(1S,2R,6S)-3-(cyclopropylmethyl)-16-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol