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Ajmalicine

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Identification
Molecular formula
C33H40N2O9
CAS number
483-04-5
IUPAC name
methyl 6,18-dimethoxy-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, ajmalicine is typically a solid. It is commonly available in its crystalline powder form.

Melting point (Celsius)
260.00
Melting point (Kelvin)
533.15
Boiling point (Celsius)
482.15
Boiling point (Kelvin)
755.30
General information
Molecular weight
558.63g/mol
Molar mass
558.6340g/mol
Density
1.2300g/cm3
Appearence

Ajmalicine typically appears as a white to off-white crystalline powder. It is often odorless and has a slightly bitter taste. Being a crystalline substance, it reflects light and can exhibit a shiny appearance under certain lighting conditions.

Comment on solubility

Solubility of Methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

The solubility of the compound with the chemical formula C33H40N2O9 can be intriguing due to its complex structure. Here are some key points to consider regarding its solubility:

  • Polarity: The presence of multiple methoxy groups suggests that the compound may have some polar characteristics, potentially enhancing its solubility in polar solvents such as water and ethanol.
  • Hydrophobic regions: The long hydrocarbon skeleton may lead to hydrophobic regions, thereby affecting its solubility in non-polar solvents.
  • Solvent interaction: The behavior of this compound in different solvents could vary widely. It is likely more soluble in organic solvents like dimethyl sulfoxide (DMSO) or chloroform, which can interact favorably with its hydrophobic regions.
  • Temperature dependency: Like many compounds, its solubility may change with temperature, possibly increasing at higher temperatures due to enhanced molecular motion.
  • Applications and relevance: Understanding the solubility can help in determining suitable conditions for extraction, formulation, and application in pharmaceuticals or other fields.

In summary, while the exact solubility of this compound in various solvents can be complex and necessitates specific experimental data, its extensive structure suggests potential solubility in a range of organic and possibly some polar solvents.

Interesting facts

Interesting Facts about Methyl 6,18-Dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-Dodecahydroyohimban-19-carboxylate

The compound Methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate is a remarkable member of the yohimbine family. Yohimbine itself is primarily known for its potential as an aphrodisiac and stimulant, and this derivative may hold even more interesting properties, making it a subject of interest in various fields of research.

Key Points of Interest

  • Structure-Activity Relationship: The presence of multiple methoxy groups could enhance the compound's lipophilicity, potentially affecting its biological activity.
  • Pharmacological Potential: Derivatives of yohimbine have been studied for various pharmacological effects, including their influence on the central nervous system and cardiovascular system.
  • Natural Product Chemistry: The synthesis of this compound showcases techniques in synthetic organic chemistry that mimic natural biosynthetic pathways.
  • Research Applications: Such compounds are evaluated in the context of developing new therapies for conditions like erectile dysfunction and anxiety.
  • Cultural Significance: Roots and bark from the yohimbe tree, which yohimbine is derived from, have been used traditionally in herbal medicine in parts of Africa for centuries.

As a student or chemist exploring this compound, it is intriguing to consider how modifications to its structure can lead to variations in efficacy and potency. Moreover, understanding the intricate balance between structure and biological function is a continuing challenge in medicinal chemistry that fuels ongoing research and discovery.

Continued study of Methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate might provide insights not only into its specific effects but also into broader applications within pharmaceuticals and therapeutic interventions. With advancements in analytical techniques, characterizing its interactions at the molecular level remains an exciting frontier for researchers.

Synonyms
Isoreserpin
1263-58-7
Salutensin
Diupres
Diutensen-R
Brinderdin
Broserpine
Cardioserpin
Hypertensan
Neoslowten
Orthoserpina
Perskleran
Pressimedin
Sederaupin
Serpaneurona
Tefaserpina
Tenserpinie
Tensionorme
Tepserpine
Transerpin
Adelfan
Adelphin
Alkaserp
Ascoserp
Banisil
Briserine
Darebon
Eberspine
Ebserpine
Elfanex
Hexaplin
Hydropres
Idoserp
Modenol
Raudixin
Reserpka
Reserutin
Resiatric
Resperine
Rivased
Rolserp
Roxynoid
Salupres
Seominal
Serpazil
Serpedin
Serpentin
Serpilum
Serpyrit
Sertensin
Supergan
Tensanyl
Tensional
Terbolan
Tylandril
Abesta
Abicol
methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Serpil
Hypertane forte
Solfo serpine
Hypercal B
l -Carpserp
Renese R
Butiserpazide-25
Marnitension simple
V-Serp
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-
Butiserpine
Gamaserpin
Mepireserpate
Resercrine
Rauloycin
Rauserpin
Rauvilid
Resedin
Resersana
Resomine
Sarpagen
Serpatone
Serpresan
Tenserlix
Veriloid
Neo-antitersol
NSC80138
Rauserpen-alk
Seda-salurepin
Serp
Hydropres ka
Mio-pressin
Nembu-serpin
Seda-recipin
Rauwiloid+
Serpasil-esidrex
Drenusil-R
Hydromox R
Serplex K
Tendoscen-compr.
Dypertane compound
Hygroton-reserpine
Butiserpazide-50
Raunormin 'orzan'
Serpasil apresoline
Adelphin-esidrex-K
Serpasil-esidrex K
Tenserpine 'assia'
Arcum R-S
Sinesalin composition
Serpentine 'pharbil'
Methylreserpate 3,4,5-trimethoxybenzoic acid
Unipres (Salt/Mix)
Methyl reserpate 3,4,5-trimethoxybenzoate (ester)
Serpasil-esidrex no. 1
Serpasil-esidrex no. 2
Methylreserpate 3,4,5-Trimethoxybenzoic acid ester
ChemDiv1_007189
Demi-Regroton (Salt/Mix)
Methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
CHEMBL357497
SCHEMBL5372168
Yohimban-16-carboxylic acid derivative of benz(g)indolo(2,3-a)quinolizine
CHEBI:91839
component of Diupres (Salt/Mix)
HMS607G17
DTXSID30925499
component of Naquival (Salt/Mix)
component of Regroton (Salt/Mix)
QEVHRUUCFGRFIF-UHFFFAOYSA-N
HMS3269P15
HMS3369J06
component of Hydropres (Salt/Mix)
component of Renese R (Salt/Mix)
component of Metatensin (Salt/Mix)
component of Salutensin (Salt/Mix)
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
NSC-80138
NSC169414
component of Diutensen-R (Salt/Mix)
AKOS004912845
component of Butiserpazide (Salt/Mix)
NSC-169414
NCGC00015888-03
NCGC00015888-04
NCGC00015888-05
NCGC00142390-01
NCGC00142390-02
3,8-dimethoxy-4-(methoxycarbonyl)-1,2,3,4,5,11,14,14a,4a,5a-decahydrobenzo[3,4 -g]indolo[2,3-a]quinolizin-2-yl 3,4,5-trimethoxybenzoate
AS-13241
Methyl reserpate 3,4,5-trimethoxybenzoate
DB-119994
Methyl reserpate 3,4,5-trimethyloxybenzoic acid
L000827
Reserpic acid methyl ester 3,4,5-trimethoxybenzoate
BRD-A71765365-001-01-6
Q27163633
Methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate #
20.alpha.-Yohimban-16.beta.-carboxylic acid,17.alpha.-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester)
3-.beta.,20-.alpha.-Yohimban-16-.beta.-carboxylic acid, 18-.beta.-hydroxy-11,17-.alpha.-dimethoxy-,methyl ester, 3,4,5-trimethoxybenzoate
3.beta.,20.alpha.-Yohimban-16.beta.-carboxylic acid, 18.beta.-hydroxy-11,17.alpha.-dimethoxy- methyl ester 3,4,5-trimethoxybenzoate (ester)
6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester
Benz(g)indolo(2,3-a)quinolizine-1-carboxylic acid, 1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-3-hydroxy-2,11-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate
Methyl 18.beta.-hydroxy-11,17.alpha.-dimethoxy-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate 3,4,5-trimethoxybenzoate (ester)
Yohimban-16-carboxylic acid,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (16.beta.,17.alpha.,18.beta.,20.alpha.)-