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Yohimbine

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Identification
Molecular formula
C21H26O3N2
CAS number
146-48-5
IUPAC name
methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
State
State

At room temperature, yohimbine is typically found as a solid. It is usually available in the form of pharmaceutical formulations.

Melting point (Celsius)
231.00
Melting point (Kelvin)
504.15
Boiling point (Celsius)
574.80
Boiling point (Kelvin)
847.95
General information
Molecular weight
354.45g/mol
Molar mass
354.4710g/mol
Density
1.4200g/cm3
Appearence

Yohimbine appears as a white crystalline powder. It is often found in the form of tablets or capsules when used as a supplement.

Comment on solubility

Solubility of Methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate (C21H26O3N2)

The solubility of methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate is influenced by several factors due to its complex structure. This compound, characterized by a large hydrocarbon backbone, presents unique solubility behaviors in different solvents.

Factors Affecting Solubility

  • Polarity: As a compound with both hydrophobic and hydrophilic characteristics, its solubility can vary greatly between polar and non-polar solvents.
  • Temperature: Increased temperature often enhances solubility due to increased kinetic energy, thus aiding dissolution.
  • pH Levels: The solubility can also be affected by the pH of the solution, which may influence the ionization of functional groups present in the molecule.

Generally, this compound tends to have:

  • Limited solubility in water: Due to its hydrophobic regions, it is not highly soluble in aqueous solutions.
  • Better solubility in organic solvents: Compounds such as ethanol, methanol, and dichloromethane are more likely to dissolve this compound effectively.

In conclusion, while the solubility of methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate can be complex, understanding the factors that influence it can aid in its practical applications and further studies.

Interesting facts

Discovering Methyl 18-Hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-Dodecahydroyohimban-19-Carboxylate

Methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate is a fascinating compound nestled within the family of yohimbine derivatives. This compound, derived from the bark of the African yohimbe tree (Pausinystalia johimbe), showcases unique structural features that contribute to its biological activity.

Biological Significance

This compound exhibits various biological properties, making it a subject of interest in pharmacological studies. Some of its notable functions include:

  • Stimulant Effects: Historically, yohimbine and its derivatives have been used as aphrodisiacs and stimulant agents.
  • Potential Therapeutic Applications: Researchers are exploring its potential use in the treatment of erectile dysfunction and as an anti-depressant.
  • Weight Management: Yohimbine has also gained attention for its role in fat loss, particularly within certain athletic and fitness communities.

Chemical Structure and Reactions

The complex chemical structure of this compound allows for a variety of interactions and reactions. Key features include:

  • Hydroxyl Groups: The presence of hydroxyl (-OH) functional groups contributes to its solubility and reactivity.
  • Stereochemistry: The stereochemical configuration plays a vital role in determining its biological activity, influencing how it interacts with receptors in the body.
  • Carboxylate Group: The carboxylate (-COO-) group can participate in esterification reactions, opening pathways for synthesis of new derivatives.

Interesting Tidbits

Scientists and students alike find this compound particularly intriguing due to:

  • Diversity of Research: The spectrum of potential applications encourages interdisciplinary studies involving chemistry, biology, and medicine.
  • Historical Context: The use of yohimbe in traditional medicine has roots dating back centuries, emphasizing the importance of ethnobotany in modern pharmacology.
  • Ongoing Studies: Current research continues to uncover new advantages and mechanisms of how this compound can be utilized optimally in various therapeutic contexts.

In conclusion, methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate stands as a prime example of how natural products can inspire modern medicinal chemistry, reaffirming the connection between nature and science.

Synonyms
Amberlite CG-400
.beta.-Yohimbine
methyl 17-hydroxy-20xi-yohimban-16-carboxylate
37247-87-3
NSC407306
Corynanthin
Isorauhimbin
CHEBI:48565
Amberlite CG 400
Methyl 17-hydroxyyohimban-16-carboxylate
methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
alpha-Yohimbine;Corynanthidine;Isoyohimbine
(-)-beta-Yohimbine; Amsonin; Amsonine; NSC 93133; beta-Yohimbin
3-Epirauwolscine; 3-epi-Rauwolscine
NSC-93133
EC-Yohimbine
A.-Yohimbine
COYNANTHINE
Methyl 17-hydroxyyohimban-16-carboxylate #
NSC19509
Yohimbol-16.alpha.-carboxylic acid, methyl ester
YOHIMBINE,?-
MLS000863574
SCHEMBL564022
MEGxp0_001106
MEGxp0_002061
Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.
CHEMBL1531132
Yohimban-16.alpha.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester
ACon1_000583
ACon1_000625
BDBM86230
DTXSID60859258
BLGXFZZNTVWLAY-UHFFFAOYSA-N
HMS2269J09
HMS3370N12
HMS3372A16
HMS3744C13
AAA48309
AAA52294
AAA54984
NSC_2866
NSC93133
BBL008941
STK801336
AKOS005612952
NCGC00015878-03
NCGC00015878-04
NCGC00015878-08
CAS_146-48-5
NCI60_001630
NCI60_003875
NCI60_003876
SMR000440723
DB-050190
DB-051541
Yohimban-16.beta.-carboxylic acid, methyl ester
L000506
Yohimban-16.alpha.-carboxylic acid, methyl ester
BRD-A51410489-001-01-4
BRD-A51410489-003-02-8
Q27121266
B0005-144043
Yohimban-16-carboxylic acid, methyl ester, (16.alpha.,17.beta.)-
Yohimban-16-carboxylic acid, methyl ester, (16.beta.,17.alpha.)-
(3beta,20alpha)-17alpha-Hydroxyyohimban-16beta-carboxylic acid methyl ester
684-546-0
Methyl 18ahydroxya3,13a diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosaa 2(10),4,6,8atetraenea19acarboxylate