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Mecamylamine

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Identification
Molecular formula
C11H21N3O2
CAS number
826-39-1
IUPAC name
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
State
State

At room temperature, Mecamylamine is typically found as a solid in the form of crystalline grains or a powdered substance.

Melting point (Celsius)
223.00
Melting point (Kelvin)
496.15
Boiling point (Celsius)
310.00
Boiling point (Kelvin)
583.15
General information
Molecular weight
231.31g/mol
Molar mass
204.2920g/mol
Density
1.1050g/cm3
Appearence

Mecamylamine usually appears as a white to off-white crystalline powder. It may become slightly discolored upon exposure to air or light. The crystalline nature of the compound gives it a gritty texture when ground to a finer powder as well.

Comment on solubility

Solubility of Methyl (15S,17S,19S)-15-Ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

The solubility of methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate is a critical factor to consider in various applications, especially in pharmacology and biochemistry. This compound, characterized by its complex structure, displays unique solubility properties that are influenced by several factors:

  • Polarity: The presence of hydroxyl and carboxyl functional groups increases the polarity of the molecule, potentially enhancing its solubility in polar solvents such as water and ethanol.
  • Hydrogen bonding: Functional groups can engage in hydrogen bonding with solvents, which can lead to significant solubility improvements in compatible media.
  • Molecular Structure: The intricate cage-like structure of this compound may hinder its solubility due to steric hindrance, which can restrict interaction with solvents.
  • Saturation: The presence of double bonds within the structure might affect the degree of saturation and the resulting solubility and stability in solution.

However, determining the exact solubility of such a compound may require:

  • Experimental data under varying conditions (temperature, pH, and concentration).
  • Assessment of its interactions with different solvents.
  • Understanding the implications of its modification by substituents.

In summary, while the solubility of methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate can be significantly influenced by its unique structural features, careful evaluation of suitable solvents and conditions is essential to fully understand its solubility behavior.

Interesting facts

Interesting Facts About Methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

This unique compound, often referred to by its systematic name, showcases a fascinating structure characterized by its multiple fused rings and functional groups. As a member of the diazapentacyclic family, it presents several intriguing aspects:

  • Complex Structure: The compound features a pentacyclic system, which is rare and highlights the intricate nature of organic chemistry. Its multiple rings contribute to its stability and reactivity.
  • Biological Relevance: Compounds like this one are often studied for their potential biological activities, which can include anti-inflammatory or anti-cancer properties, making them significant in medicinal chemistry.
  • Stereochemistry: With specific configurations at several chiral centers (15S, 17S, 19S), the compound can exhibit distinct biological activities depending on its stereochemical arrangement. This fact underscores the importance of chirality in pharmaceutical applications.
  • Potential Synthetic Routes: Chemists are exploring various synthetic pathways to create this compound. Understanding its synthesis can lead to innovations in organic synthesis and the development of new materials.
  • Applications in Research: The compound's structure provides a robust platform for modifications, helping researchers develop derivatives that can enhance pharmacological properties or target specific biological pathways.
  • Environmental Impact: Studies are being conducted on how such compounds degrade in the environment and their potential effects on ecosystems, which is crucial for sustainable chemistry.

In the words of a renowned chemist, "The beauty of chemistry lies in the intricate dance of atoms, creating compounds that can change the world." This compound is an excellent example of this idea, reflecting the complex interplay of elements that contribute to its unique properties and potential applications.


As research progresses, methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate could unlock new avenues in both theoretical and applied sciences, making it a compound worth studying further.

Synonyms
vincamine
1617-90-9
Pervincamine
Devincan
Arteriovinca
Angiopac
Minorine
Vincamidol
(+)-Vincamine
Oxygeron
Vincafor
Vincagil
Vincamin
Monorin
Novicet
Methyl vincaminate
Anasclerol
Vincafolina
Vincapront
Vincasaunier
Vinkametrin
Decincan
Devinkan
Equipur
Tripervan
Vincadar
Vincamina
Vincimax
Perval
Pervone
Ocu-vinc
Vincamina [DCIT]
Vincaminum
Vraap
Cetal retard
Vincaminum [INN-Latin]
Vincamine [INN:BAN:DCF]
Vincachron
Vincapan
Minorin
Vinodrel retard
Vinca-Ecobi
Vinca-Minor
HSDB 7150
Alkaloid obtained from Vinca minor
Anasclerol (base)
UNII-996XVD0JHT
EINECS 216-576-3
996XVD0JHT
NSC 91998
Vincamine (INN)
Cetal retard (TN)
CHEBI:9985
DTXSID9040134
14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
VINCAMINE [INN]
VINCAMINE [MI]
VINCAMINE [HSDB]
NSC-91998
VINCAMINE [MART.]
VINCAMINE [WHO-DD]
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-
DTXCID7020134
VINCAMINE [EP MONOGRAPH]
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16.)
Cerebroxine
Vincaminum (INN-Latin)
VINCAMINE (MART.)
methyl 14beta-hydroxy-14,15-dihydro-3alpha,16alpha-eburnamenine-14alpha-carboxylate
Vinvasaunier
Sostenil
Vincafarm
Vincalen
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
cis-Vincamine
VINCAMINE (EP MONOGRAPH)
(+)-cis-Vincamine
(3.ALPHA.,14.BETA.,16.ALPHA.)-14,15-DIHYDRO-14-HYDROXYEBURNAMENINE-14-CARBOXYLIC ACID METHYL ESTER
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3.alpha.,14.beta.,16.alpha.)-
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo(9.6.2.0^(2,7).0^(8,18).0^(15,19))nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo(9.6.2.02,7.08,18.015,19)nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Methyl vincaminic acid
C04AX07
(3.alpha.,14.beta.,16.alpha.)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid, methyl ester
(3alpha, 14beta, 16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
(3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
(3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid, methyl ester
13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-12-hydroxy-1H-indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5) naphthyridine-12-carboxylic acid methyl ester
216-576-3
1h-indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5)naphthyridine, eburnamenine-14-carboxylic acid deriv.
1h-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine, eburnamenine-14-carboxylic acid deriv.
rxprrqlkfxbcsj-dqvlvphssa-n
rxprrqlkfxbcsj-givpxcgwsa-n
rxprrqlkfxbcsj-mnlritnhsa-n
MFCD00078054
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methylester, (3a,14b,16a)-
Vincamine base
NCGC00094824-01
Prestwick_495
CAS-1617-90-9
Vincamine, 98%
Vincamine (Standard)
Prestwick0_000271
Prestwick1_000271
Prestwick2_000271
Prestwick3_000271
BSPBio_000142
GTPL349
MLS002154249
SCHEMBL147179
SPBio_002361
BPBio1_000158
CHEMBL1165342
BCBcMAP01_000080
HY-B1021R
HMS1568H04
HMS2095H04
HMS2268C20
HMS3712H04
BCP05837
HY-B1021
Methyl (41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
Tox21_111342
Tox21_301968
s3891
AKOS015896471
Tox21_111342_1
CCG-208544
CS-4536
DB13374
FV65205
KS-5179
SMP1_000314
Vincamine, analytical reference material
NCGC00184983-01
NCGC00184983-03
NCGC00255542-01
AC-22625
SMR000112509
NS00006858
C09251
D08677
Q416225
BRD-K40902647-001-03-7
methyl (3alpha,14beta,16alpha)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-,methyl ester, (3alpha,14beta,16alpha)-
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0?,?.0?,??.0??,??]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
methyl(15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Methyl(41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate