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Codeine

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Identification
Molecular formula
C18H21NO3
CAS number
76-57-3
IUPAC name
(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
State
State

At room temperature, codeine is typically a solid. It is generally supplied in a crystalline powder form and tends to remain stable under standard temperature and pressure conditions.

Melting point (Celsius)
154.00
Melting point (Kelvin)
427.15
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.15
General information
Molecular weight
299.36g/mol
Molar mass
299.3640g/mol
Density
1.3400g/cm3
Appearence

Codeine appears as white or nearly white crystalline powder. It is odorless or may have a faint odor and has a bitter taste. The crystals or crystalline powder is usually fine and shows some degree of luster.

Comment on solubility

Solubility of (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol

The solubility of (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol is influenced by its intricate chemical structure, which includes multiple functional groups and a complex ring system. Understanding its solubility involves considering several key factors:

  • Polarity: The presence of oxygen atoms and functional groups such as methoxy contributes to a certain degree of polarity, which can enhance solubility in polar solvents.
  • Hydrogen Bonding: The hydroxyl group (-OH) can engage in hydrogen bonding, potentially increasing solubility in water.
  • Hydrophobic Regions: The hydrophobic parts of the molecule may impede solubility in highly polar solvents.
  • Solvent Interaction: Solubility is highly dependent on the solvent type; for example, it might dissolve better in organic solvents than in water.

In summary, while definitive solubility data may be limited, it can be anticipated that this compound would exhibit moderate solubility characteristics primarily influenced by its polar functional groups and ring structure. As noted, "like dissolves like," which underscores the importance of matching solubility to solvent characteristics for optimal results.

Interesting facts

Interesting Facts about (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol

This complex compound is a fascinating example of intricate organic chemistry and illustrates the rich diversity found in tetraene structures. Its systematic naming reveals a lot about its molecular framework, highlighting unique features such as:

  • Stereochemistry: The use of specific stereochemistry notation (1S, 12S, 14R) suggests that this compound possesses several chiral centers, which can lead to interesting variations in its biological activity. In asymmetric synthesis, even slight changes in configuration can result in entirely different properties.
  • Oxazetidine functionality: Incorporating an oxazetidine group (the 11-oxa-4-azatetracyclo component) indicates potential applications as a medicinal agent, perhaps exhibiting interesting pharmacological properties linked to its unique ring structure.
  • Methoxy and methyl groups: The presence of methoxy and methyl substituents enhances its biological activity, which could be exploited in the development of drug interactions and improving bioavailability.
  • Tetramolecular system: Being categorized within a tetracyclic framework highlights how this compound might engage in *non-linear dynamic behaviors*, which are relevant in the study of complex molecular interactions.

In scientific research, compounds like this often serve as key building blocks in the synthesis of larger, more complex molecules. Additionally, they can offer insights into natural product chemistry, particularly in the exploration of plant-derived substances or other eco-friendly resources. As chemistry students dive into the study of such compounds, they uncover the underlying principles of stereochemistry, functional groups, and their remarkable effects on the way molecules interact in biological systems.

In the words of renowned chemist Linus Pauling, "The best way to have a good idea is to have lots of ideas." This statement rings especially true in organic chemistry, where each unique structure may lead to revolutionary advancements in pharmaceuticals and materials science. The exploration of this compound not only enhances our understanding but also paves the way for future innovations.

Synonyms
galanthamine
Galantamine
357-70-0
(-)-Galanthamine
Lycoremin
Lycoremine
Galantamina
Jilkon
Galanthaminum
Galantamin
(-)-Galantamine
Galantaminum
NSC 100058
Galantaminum [INN-Latin]
Galantamina [INN-Spanish]
(+/-)-Galantamine
Razadyne ER
Bodamine
BRN 0093736
HSDB 7361
UNII-0D3Q044KCA
0D3Q044KCA
CHEBI:42944
(+/-)-Galanthamine
Reminyl (TN)
Galantamine, (+/-)-
Galanthamine, (+/-)-
CHEMBL659
NSC-100058
(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol
23173-12-8
DTXSID2045606
4-27-00-02184 (Beilstein Handbook Reference)
1T835Z585R
(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
Galantaminum (INN-Latin)
Galantamina (INN-Spanish)
(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol
6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6R,8aS)-
GNT
(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-14-ol
(4aS,6R,8aS)-3-Methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4aH-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol
6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aR,6S,8aR)-rel-
6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4AS,6R,8AS)
Galantamine (USAN/INN)
Galantamine [USAN:INN:BAN]
SR-05000001783
1qti
Galanthamine, 12
6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6R,8aS)-
MFCD00867189
Spectrum_001271
1dx6
Galanthamine (Standard)
GALANTAMINE [MI]
Prestwick0_000588
Prestwick1_000588
Prestwick2_000588
Prestwick3_000588
Spectrum3_001738
Spectrum4_000839
Spectrum5_001673
GALANTAMINE [INN]
GALANTAMINE [HSDB]
GALANTAMINE [USAN]
Probes1_000055
Probes2_000395
GALANTAMINE [VANDF]
SCHEMBL2577
BSPBio_000436
BSPBio_003416
GALANTAMINE [WHO-DD]
KBioGR_001417
KBioSS_001751
BIDD:GT0517
DivK1c_000590
SPBio_002655
BPBio1_000480
GTPL6693
SCHEMBL3293474
UNII-1T835Z585R
ASUTZQLVASHGKV-JDFRZJQESA-
BDBM10404
KBio1_000590
KBio2_001751
KBio2_004319
KBio2_006887
KBio3_002636
N06DA04
ASUTZQLVASHGKV-JDFRZJQESA-N
NINDS_000590
GLXC-03030
HMS2089H03
HMS3885C10
Pharmakon1600-01501202
MSK10278
HY-76299R
NSC759861
s3866
AKOS015965330
CCG-212961
CS-1217
DB00674
FH15703
NSC-759861
SDCCGMLS-0066737.P001
IDI1_000590
SMP1_000131
NCGC00017256-05
NCGC00017256-11
NCGC00017256-17
NCGC00024731-02
(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofurol[3a,3,2,-ef][2]benzazepin-6-ol
6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-
AC-20240
AC-34328
AS-56354
HY-76299
SBI-0051689.P002
NS00003061
A11538
C08526
D04292
EN300-708805
AB00053614-09
AB00053614_10
AC-542/20973006
Q412690
Galanthamine ( Jilkon, Lycoremine, Nivalin and oth
SR-05000001783-4
BRD-K49481516-001-01-5
BRD-K49481516-004-03-5
BRD-K49481516-004-04-3
BRD-K49481516-004-09-2
BRD-K49481516-004-18-3
(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-ol
(4aS,6R,8aS)-3-methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4aH-(1)benzofuro(3a,3,2-ef)(2)benzazepin-6-ol
1008759-59-8
6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4A.ALPHA.,6.BETA.,8AR*)-
6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aalpha,6beta,8ar*)-
InChI=1/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1