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Melatonin

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Identification
Molecular formula
C13H16N2O2
CAS number
73-31-4
IUPAC name
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
State
State
Melatonin is typically found in a solid state at room temperature, existing as crystalline powder.
Melting point (Celsius)
117.00
Melting point (Kelvin)
390.00
Boiling point (Celsius)
410.00
Boiling point (Kelvin)
683.00
General information
Molecular weight
232.28g/mol
Molar mass
232.2780g/mol
Density
1.1741g/cm3
Appearence

Melatonin appears as a white to off-white crystalline powder. It is soluble in alcohol and alkaline solutions, slightly soluble in water, and practically insoluble in ether.

Comment on solubility

Solubility of N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide

N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide, with the chemical formula C13H16N2O2, presents interesting solubility characteristics that are essential for its applications in various fields.

General Observations on Solubility

This compound exhibits moderate to high solubility in various organic solvents and limited solubility in water. The solubility is influenced by several factors:

  • Polarity: The presence of the acetamide functional group contributes to some degree of polarity, which allows for solubility in polar organic solvents.
  • Hydrogen Bonding: The ability of the acetamide group to form hydrogen bonds can enhance solubility in solvents capable of participating in such interactions.
  • Hydrophobic Character: The methoxy group and indole structure add hydrophobic characteristics, making it less soluble in water.

Solubility in Common Solvents

The following points summarize the solubility behavior of N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide:

  • Solvents like chloroform and ethanol: Generally show good solubility.
  • Water: Limited solubility, which could impact its bioavailability in aqueous systems.
  • Dimethyl sulfoxide (DMSO): Often provides a high degree of solubility due to its excellent solvent properties.

In conclusion, the solubility of N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide is a critical factor that influences its practical applications, particularly in areas such as pharmaceuticals and materials science. Understanding its solubility profile can guide researchers in effectively utilizing this compound in various chemical and biological processes.

Interesting facts

Interesting Facts about N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide

N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide is a fascinating compound that showcases the intriguing intersection between chemistry and biology. Here are some notable points about this unique molecule:

  • Structural Composition: The compound has a distinctive structure featuring an indole ring, which is a key feature in many biologically active compounds. The presence of the methoxy group adds to its chemical complexity and potential reactivity.
  • Potential Biological Activity: Compounds with indole structures, such as this one, are often studied for their effects on the central nervous system. They may have therapeutic potentials in treating various conditions, including mood disorders and cognitive dysfunctions.
  • Synthesis Interest: The synthesis of this compound can involve multi-step reactions that are both challenging and rewarding. This makes it an interesting target for organic chemists looking to explore new synthesis pathways.
  • Research Applications: Due to its structure, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide could serve as a template for developing novel drugs, making it a significant compound in drug discovery efforts.

As with many compounds in medicinal chemistry, the study of N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide illustrates the complexity of the interactions between molecular structure and biological function. The ongoing research into compounds like this one may lead to new insights in pharmacology and therapeutic applications.

Synonyms
Melatonin
73-31-4
Melatonine
N-Acetyl-5-methoxytryptamine
Circadin
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide
5-Methoxy-N-acetyltryptamine
Melatol
N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide
Melovine
8041-44-9
Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-
N-[2-(5-methoxyindol-3-yl)ethyl]acetamide
N-acetyl-5-methoxy-tryptamine
CCRIS 3472
NSC 113928
Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)-
UNII-JL5DK93RCL
JL5DK93RCL
Acetamide, N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-
N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide
EINECS 200-797-7
MFCD00005655
NSC-56423
5-methoxy n-acetyl-tryptamine
NSC-113928
BRN 0205542
DTXSID1022421
CHEBI:16796
HSDB 7509
BCI-049
CHEMBL45
NSC113928
J5.258B
DTXCID002421
Melatonex
Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]-
Melatonin (JAN)
5-22-12-00042 (Beilstein Handbook Reference)
NSC56423
CAS-73-31-4
NCGC00015680-11
MELATONIN [JAN]
MELATONIN (MART.)
MELATONIN [MART.]
MELATONIN (USP-RS)
MELATONIN [USP-RS]
Melatonina
Melapure
Posidorm
Primex
WLN: T56 BMJ D2MV1 GO1
[3H]melatonin
Melatonina (TN)
[3H]-melatonin
ML1
SMR000326666
N-(2-(5-methoxyindol-3-yl)ethyl)-Acetamide
N-[2-(5-methoxyindol-3-yl)ethyl]-Acetamide
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide
SR-01000075559
somease
[3H]MLT
Melatobel
Melaxen
Melatonine?
3-(n-acetyl-2-aminoethyl)-5-methoxyindole
Guna-dermo
Amerix Melatonin
Safrel Melatonin
3-(N-Acetyl-2-aminoethyl)-5-methoxyindole;N-Acetyl-5-methoxytryptamine
Melatonin Phenolic
Melatobel (TN)
TNP00300
Melatonin1527
Prestwick_312
N-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-acetamide
Therapeutic Melatonin
Spectrum_000185
MELATONIN [DSC]
Guna-dermo (Salt/Mix)
MELATONIN [MI]
MELATONIN [HSDB]
Prestwick0_000458
Prestwick1_000458
Prestwick2_000458
Prestwick3_000458
Spectrum2_001344
Spectrum3_001393
Spectrum4_000066
Spectrum5_001745
Lopac-M-5250
MELATONIN [VANDF]
M1105
ChemDiv2_003916
M 5250
Melatonin, >=99.5%
MELATONIN [WHO-DD]
Lopac0_000787
Oprea1_104553
Oprea1_814234
SCHEMBL19018
BSPBio_000536
BSPBio_003006
GTPL224
KBioGR_000591
KBioSS_000665
MELATONIN [EMA EPAR]
Acetamide, {N-[2-(5-methoxyindol-3-yl)ethyl]-}
MLS000859594
MLS001055382
MLS001240204
BIDD:ER0618
DivK1c_000353
SPECTRUM1500690
Melatonin - Bio-X trade mark
SPBio_001527
SPBio_002475
Melatonin (synth.) ultra-pure
MELATONIN [GREEN BOOK]
BDBM9019
BPBio1_000590
GTPL1357
Melatonin Rapid Release Gelcaps
Acetamide, {N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-}
HMS501B15
KBio1_000353
KBio2_000665
KBio2_003233
KBio2_005801
KBio3_002226
Melatonin 1.0 mg/ml in Methanol
NINDS_000353
GLXC-25215
HMS1380B22
HMS1569K18
HMS1921E04
HMS2089F09
HMS2096K18
HMS2233D23
HMS3262M16
HMS3370J20
HMS3413P14
HMS3654A22
HMS3677P14
HMS3713K18
HMS3884M05
Melatonin (synth.) standard-grade
BCP28154
HY-B0075
Tox21_110195
Tox21_201527
Tox21_302926
Tox21_500787
CCG-38837
HSCI1_000400
Melatonin, powder, >=98% (TLC)
STK386880
Melatonin Rapid Release Gelcaps 5 mg
AKOS000276269
Tox21_110195_1
CS-1769
DB01065
FA01297
KS-1454
LP00787
SDCCGMLS-0065812.P001
SDCCGMLS-0065812.P002
SDCCGSBI-0050765.P003
IDI1_000353
IDI1_002631
SMP2_000309
N-acetyl-5-methoxy-tryptamine Melatonine
NCGC00015680-01
NCGC00015680-02
NCGC00015680-03
NCGC00015680-04
NCGC00015680-05
NCGC00015680-06
NCGC00015680-07
NCGC00015680-08
NCGC00015680-09
NCGC00015680-10
NCGC00015680-12
NCGC00015680-13
NCGC00015680-14
NCGC00015680-15
NCGC00015680-16
NCGC00015680-18
NCGC00015680-34
NCGC00015680-35
NCGC00090727-01
NCGC00090727-02
NCGC00090727-03
NCGC00090727-04
NCGC00090727-05
NCGC00090727-06
NCGC00090727-07
NCGC00090727-08
NCGC00090727-09
NCGC00256404-01
NCGC00259077-01
NCGC00261472-01
AC-10019
BA164660
NCI60_004378
SY051401
AB00053279
EU-0100787
NS00009598
S1204
SW196607-4
C01598
D08170
M02088
AB00053279-10
AB00053279_12
EN300-6486827
{N-[2-(5-methoxyindol-3-yl)ethyl]-} Acetamide
L001261
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-Acetamide
Q180912
SR-01000075559-1
SR-01000075559-6
SR-01000075559-7
SR-01000075559-8
{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} Acetamide
BRD-K97530723-001-07-6
BRD-K97530723-001-11-8
BRD-K97530723-001-19-1
BRD-K97530723-001-20-9
F1929-1777
Melatonin, British Pharmacopoeia (BP) Reference Standard
Z1191880499
0E2B08C1-B325-45B1-8939-6F9081EFDFA4
Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]- (6CI,8CI)
Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]- (9CI)
Melatonin, United States Pharmacopeia (USP) Reference Standard
Melatonin, Pharmaceutical Secondary Standard; Certified Reference Material
200-797-7