Skip to main content

Yohimbine

ADVERTISEMENT
Identification
Molecular formula
C21H26N2O3
CAS number
146-48-5
IUPAC name
(1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6-oxa-7-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7-dien-17-ol
State
State

At room temperature, yohimbine is found in a solid state. It is typically used in its hydrochloride salt form for its pharmaceutical applications.

Melting point (Celsius)
231.00
Melting point (Kelvin)
504.15
Boiling point (Celsius)
438.00
Boiling point (Kelvin)
711.15
General information
Molecular weight
354.45g/mol
Molar mass
354.4640g/mol
Density
1.2830g/cm3
Appearence

Yohimbine appears as a crystalline solid. It is typically white, though it can sometimes be found in an off-white or slightly yellowish color. The compound is odorless with a distinctly bitter taste.

Comment on solubility

Solubility of (1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6-oxa-7-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7-dien-17-ol

The compound (1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6-oxa-7-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7-dien-17-ol exhibits interesting solubility characteristics. The solubility of such complex organic compounds can often be influenced by several factors:

  • Polarity: Given its stearic structure and functional groups, the compound is likely to have varying degrees of polarity which affects its solubility in different solvents, particularly polar versus non-polar solvents.
  • Hydrogen Bonding: The presence of certain functional groups can engage in hydrogen bonding, enhancing solubility in polar solvents like water.
  • Temperature: Increasing the temperature can aid in solubilizing compounds by increasing molecular motion, allowing for better interaction with solvents.
  • pH Levels: The solubility may also change depending on the pH of the solution, particularly if the compound can ionize under certain conditions.

In conclusion, precise predictions of solubility for this compound may require empirical testing or computational predictions, as the specific interactions between molecules can vary widely. As a general rule, compounds like this are often more soluble in organic solvents which are structurally similar to the compound itself.

Interesting facts

Interesting Facts about (1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6-oxa-7-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7-dien-17-ol

This complex organic compound showcases an intriguing molecular structure that belongs to a class of cyclic compounds. Its significance stems from the diverse applications it holds in various scientific fields. Here are some fascinating aspects regarding this compound:

  • Structural Complexity: The compound features a highly intricate framework characterized by multiple fused rings, making it a compelling subject of study in structural chemistry.
  • Potential Biological Activity: Preliminary research suggests that compounds with similar structures may exhibit biological properties, leading to potential applications in medicinal chemistry.
  • Synthesis Challenges: The multi-step synthetic process involved in its preparation often poses challenges, which can be both a deterrent and a motivator for chemists aiming for innovative methods.
  • Natural Product Analogs: This compound may serve as an analog for natural products, potentially aiding in the development of new pharmaceuticals inspired by nature.

As a student of chemistry, one might find it fascinating to explore the following:

  1. How does the presence of the oxa (oxygen) and azapenta (nitrogen) components influence the compound's chemical properties?
  2. What are the implications of the stereochemistry represented by the configuration notations in the compound's name?
  3. Are there possible routes for further modification of the compound's structure that could enhance its pharmacological benefits?

In the words of a renowned chemist, “The beauty of chemistry lies in its intricacy and the endless possibilities for innovation that arise from understanding complex compounds." This statement resonates profoundly with the study of (1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6-oxa-7-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7-dien-17-ol.

Synonyms
Androisoxazole
Androxan
Neo-ponden
360-66-7
Androisossazolo [Italian]
Androisossazolo
UNII-6WRG30P3CG
6WRG30P3CG
17-Methylandrostano(3,2-c)isoxazol-17-ol
17-Methyl-5alpha-androstano(3,2-c)isoxazol-17beta-ol
ANDROISOXAZOLE [MI]
17-alpha-Methylandrostan(3,2-c)isoxazol-17-beta-ol
17-beta-Hydroxy-17-alpha-methylandrostano(3,2-c)isoxazole
17-beta-Idrossi-17-alpha-metilandrostan(3,2-c)isossazolo [Italian]
17-beta-Idrossi-17-alpha-metilandrostan(3,2-c)isossazolo
5-alpha-ANDROSTANO(3,2-c)ISOXAZOL-17-beta-OL, 17-METHYL-
17.BETA.-HYDROXY-17.ALPHA.-METHYLANDROSTANO(3,2-C)ISOXAZOLE
(5.ALPHA.,17.BETA.)-17-METHYLANDROSTANO(3,2-C)ISOXAZOL-17-OL
17-.alpha.-Methylandrostan(3,2-c)isoxazol-17-.beta.-ol
17-.beta.-Idrossi-17-.alpha.-metilandrostan(3,2-c)isossazolo
SCHEMBL145991
17-.beta.-Hydroxy-17-.alpha.-methylandrostano(3,2-c)isoxazole
5-.alpha.-Androstano(3,2-c)isoxazol-17-.beta.-ol, 17-methyl-
Androstano[3,2-c]isoxazol-17-ol, 17-methyl-, (5.alpha.,17.beta.)-
DTXSID40957423
CHEBI:135407
1,10a,12a-Trimethyl-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-8-oxa-7-aza-dicyclopenta(a,H)phenanthren-1-ol
1,10a,12a-Trimethyl-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-8-oxa-7-aza-dicyclopenta[a,H]phenanthren-1-ol
FA150909
Q4759465
(5ALPHA,17BETA)-17-METHYLANDROSTANO(3,2-C)ISOXAZOL-17-OL
17BETA-HYDROXY-17ALPHA-METHYLANDROSTANO(3,2-C)ISOXAZOLE
Androstano(3,2-c)isoxazol-17-ol, 17-methyl-, (5alpha,17beta)-
(1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6-oxa-7-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7-dien-17-ol