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Yohimbine

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Identification
Molecular formula
C21H26N2O3
CAS number
146-48-5
IUPAC name
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
State
State

At room temperature, yohimbine is generally a solid substance, appearing as a fine, crystalline powder.

Melting point (Celsius)
288.00
Melting point (Kelvin)
561.15
Boiling point (Celsius)
378.50
Boiling point (Kelvin)
651.70
General information
Molecular weight
390.45g/mol
Molar mass
390.4530g/mol
Density
1.2540g/cm3
Appearence

Yohimbine is a white, odorless crystalline powder that is slightly soluble in water and more soluble in organic solvents. It is usually provided as a hydrochloride salt due to its higher solubility compared to the free base form.

Comment on solubility

Solubility of Methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

The solubility of complex organic compounds such as methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate can vary significantly based on several factors. Here are some points to consider:

  • Polarity: The presence of multiple functional groups, including methoxy and carboxylate, increases the polarity of the compound, which can enhance solubility in polar solvents like water.
  • Hydrophobic Regions: The dodecahydroyohimban structure introduces hydrophobic characteristics that may lead to limited solubility in highly polar solvents.
  • Solvent Compatibility: The compound is likely to exhibit good solubility in organic solvents such as ethanol or methanol, owing to its organic nature and structural components.
  • Temperature Influence: As with many compounds, solubility may increase with temperature, allowing for better dissolution in a given solvent.
  • pH Sensitivity: Variations in pH can affect ionization, thus altering the solubility profile of carboxylate groups within the compound.

It is essential to consider these factors when determining the solubility of this compound in practical applications. As a general observation, "solubility is a complex interplay of molecular interactions and environmental conditions." Therefore, experimental validation is crucial to ascertain the exact solubility conditions for any practical use of this compound.

Interesting facts

Interesting Facts about Methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

Methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate, commonly known in the realm of natural products chemistry, is a compound of great interest due to its complex structure that is derived from the alkaloid yohimbine. Here are some intriguing aspects of this compound:

  • Structural Complexity: The intricate and multi-ringed structure of this compound signifies an advanced level of stereochemistry, emphasizing the importance of chirality in pharmacological effectiveness and biological interactions.
  • Natural Origins: Yohimbine, the parent structure, is obtained from the bark of the Pausinystalia johimbe tree, native to Africa, showcasing the compound's organic and historical roots in traditional medicine practices.
  • Potential Pharmacological Uses: Compounds related to yohimbine have been researched for various applications, notably in treating erectile dysfunction and as a potential antidepressant by acting on adrenaline receptors.
  • Role of Methoxy Groups: The presence of multiple methoxy groups in the compound is noteworthy. These groups often enhance the bioavailability of the compound and can influence its pharmacokinetics and pharmacodynamics.
  • Research and Development: In contemporary studies, the systematic exploration of such complex compounds opens pathways for the synthesis of new therapeutic agents, emphasizing the connection between traditional knowledge and modern scientific advancements.

In conclusion, the study of methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate embodies both the challenges and the excitement that chemical research entails, bridging nature’s offerings with innovative scientific exploration.

Synonyms
DESERPIDINE
131-01-1
Harmonyl
Raunormine
Recanescin
Deserpidin
Recanescine
Canescine
Desepridine
Raunormin
Canescin
Reserpidine
Desmethoxyreserpine
Tranquinil
11-Demethoxyreserpine
11-Desmethoxyreserpine
Deserpidina
Deserpidinum
Halmonyl
Deserpidinum [INN-Latin]
Deserpidina [INN-Spanish]
Lilly 22641
Deserpidine, (-)-
CHEBI:27478
EINECS 205-004-8
Deresperine
NSC 72138
NSC-72138
Deserpidic acid, methyl ester, 3,4,5-trimethoxybenzoate
Deserpidine (INN)
BRN 0101820
A-11025
DTXSID8020383
UNII-9016E3VB47
NSC72138
Methyl 18beta-hydroxy-17alpha-methoxy-3beta,20alpha-yohimban-16beta-carboxylate, 3,4,5-trimethoxybenzoate (ester)
9016E3VB47
DTXCID80383
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Methyl 17alpha-methoxy-18beta-(3,4,5-trimethoxybenzoyloxy)-3beta,20alpha-yohimban-16beta-carboxylat
Yohimban-16-carboxylic acid,17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester,(3b,16b,17a,18b,20a)-
4-25-00-01282 (Beilstein Handbook Reference)
ENDURONYL COMPONENT DESERPIDINE
(3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-17-alpha-methoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester)
methyl (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
Methyl 17alpha-methoxy-18beta-((3,4,5-trimethoxybenzoyl)oxy)-3beta,20alpha-yohimban-16beta-carboxylate
NCGC00168786-01
NCGC00168786-02
ORETICYL FORTE COMPONENT DESERPIDINE
DESERPIDINE [INN]
Deserpidinum (INN-Latin)
Deserpidina (INN-Spanish)
Deserpidine [INN:BAN]
DESERPIDINE (MART.)
DESERPIDINE [MART.]
methyl (3beta,16beta,17alpha,18beta,20alpha)-17-(methyloxy)-18-({[3,4,5-tris(methyloxy)phenyl]carbonyl}oxy)yohimban-16-carboxylate
Halmonyl (TN)
CAS-131-01-1
(3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-((3,4,5-trimethoxybenzoyl)oxy)yohimban-16-carboxylic acid methyl ester
methyl (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-((3,4,5-trimethoxybenzoyl)oxy)yohimban-16-carboxylate
MD-0232
Deserpidine (Standard)
DESERPIDINE [MI]
DESERPIDINE [VANDF]
DESERPIDINE [WHO-DD]
MLS006010113
SCHEMBL259343
GTPL7064
CHEMBL1200515
C02AA05
DESERPIDINE [ORANGE BOOK]
CVBMAZKKCSYWQR-WCGOZPBSSA-N
METHYL 17.ALPHA.-METHOXY-18.BETA.-((3,4,5-TRIMETHOXYBENZOYL)OXY)-3.BETA.,20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLATE
Tox21_112646
Tox21_113102
BDBM50480272
EX-A10762
AKOS015896464
DB01089
HY-107339R
DESERPIDINE COMPONENT OF ENDURONYL
(1S,2R,3R,4aS,13bR,14aS)-Methyl 2-methoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate
17.alpha.-Methoxy-18.beta.-[(3,4,5-trimethoxybenzoyl)oxy]-3.beta.,20.alpha.-yohimban-16.beta.-carboxylic acid methyl ester
SMR004701248
HY-107339
CS-0028177
NS00008754
DESERPIDINE COMPONENT OF ORETICYL FORTE
C06541
D08194
F82150
EN300-19736832
Q5263885
BRD-K29462201-001-01-9
BRD-K29462201-001-02-7
205-004-8
Benz[g]indolo[2, 1,2,3,4,4a,5,7,8,-13,13b,14,14a-dodecahydro-3-hydroxy-2-methoxy-, methyl ester, 3,4,5-trimethoxybenzoate
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-[(3,4,5-trimethoxyphenyl)carbonyloxy]-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
Yohimban-16-carboxylic acid, 17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16b,17a,18b,20a)-