2-(5-methoxyindol-3-yl)ethylamine
acetic anhydride
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With pyridine In dichloromethane | 100% |
In 1,2-dichloro-ethane at 0℃; for 1h; | 96% |
With triethylamine | 95% |
2-(5-methoxyindol-3-yl)ethylamine
acetyl chloride
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
In dichloromethane at 25 - 30℃; Temperature; | 98.3% |
With triethylamine In dichloromethane at 20℃; | |
With triethylamine In dichloromethane at 0 - 20℃; for 5h; |
2-(5-methoxyindol-3-yl)ethylamine
potassium thioacetate
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In ethyl acetate at 20℃; Electrochemical reaction; | 97% |
2-(5-methoxyindol-3-yl)ethylamine
1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.3h; | 93% |
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran at -78 - -33℃; for 1h; | 92% |
vinyl acetate
2-(5-methoxyindol-3-yl)ethylamine
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With agarose immobilized acetyltransferase from Mycobacterium smegmatis (MsAcT) In aq. phosphate buffer; dimethyl sulfoxide at 25℃; under 760.051 Torr; for 0.0833333h; pH=8.0; Flow reactor; Enzymatic reaction; | 92% |
2-(5-methoxyindol-3-yl)ethylamine
thioacetic acid
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation; | 92% |
N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 10h; Electrolysis; Green chemistry; | 92% |
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In water; acetonitrile for 20h; Irradiation; | 81% |
5-methoxytryptamine hydrochloride
acetic anhydride
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 25℃; for 3h; | 90% |
boron trifluoride methanol complex
Nb-acetyl-1-hydroxytriptamine
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
In methanol Heating; | 80% |
methanol
Nb-acetyl-1-hydroxytriptamine
A
bufotenin
B
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With sulfuric acid Heating; | A 7% B 80% |
methanol
Nb-acetyl-1-hydroxytriptamine
A
N-Acetyltryptamine
B
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With boron trifluoride for 0.666667h; Product distribution; Further Variations:; Reagents; Temperatures; reaction times; Elimination; methoxylation; Heating; | A 5% B 80% |
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl) iridium; caesium carbonate at 150℃; for 48h; Inert atmosphere; Sealed tube; | 78% |
N-[(methyl)carbonyl]-2-pyrroline
4-methoxyphenylhydrazine hydrochloride
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
In ethanol; water; acetic acid for 0.333333h; Cyclization; Fischer synthesis; Heating; | 75% |
N-[2-(1-methanesulfonyl-5-methoxy-2,3-dihydro-1H-indol-3-yl)-ethyl]-acetamide
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With sulfuric acid at 0℃; for 0.5h; | 72% |
2-(5-methoxyindol-3-yl)ethylamine
ethyl acetate
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With acetic acid at 80℃; for 20h; Sealed tube; | 70% |
With agarose immobilized acetyltransferase from Mycobacterium smegmatis (MsAcT) In aq. phosphate buffer; dimethyl sulfoxide at 25℃; under 760.051 Torr; for 0.0833333h; pH=8.0; Flow reactor; Enzymatic reaction; |
N-acetyl-5-hydroxytryptamine
dimethyl sulfate
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 26℃; for 2.25h; | 61.4% |
2-(2,4-dinitrophenylsulfenyl)melatonin
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With nickel In 1,4-dioxane; water at 80 - 90℃; for 20h; until it lost its coloration; | 54% |
N-allylacetamide
carbon monoxide
4-methoxyphenylhydrazine hydrochloride
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
Stage #1: N-allylacetamide; carbon monoxide With hydrogen; acetylacetonatodicarbonylrhodium(l); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In water; toluene at 70℃; under 7500.75 Torr; for 30h; Hydroformylation; Stage #2: 4-methoxyphenylhydrazine hydrochloride Condensation; Stage #3: With acetic acid for 0.166667h; Cyclization; Fischer indole reaction; Heating; Further stages.; | 44% |
4-methoxyphenylhydrazine hydrochloride
1-acetyl-2-methoxypyrrolidine
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
In water; acetic acid Heating; | 32% |
Conditions | Yield |
---|---|
With methanesulfonyl chloride; triethylamine In chloroform Further byproducts given; | A 7% B 7% C 12% D 7% |
Conditions | Yield |
---|---|
With ethanol; sodium Erwaermen des Reaktionsprodukts mit Essigsaeure und Acetanhydrid auf 100grad; |
Nb,Nb-diacetyl-5-methoxytryptamine
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With ammonium hydroxide In methanol Yield given; |
(E)-3-(2-nitroethenyl)-5-methoxyindole
acetic anhydride
A
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With hydrogen; nickel In tetrahydrofuran under 3040 Torr; for 10h; Ambient temperature; | |
With sodium hydroxide; hydrogen; nickel 1.) THF, RT, 4 atm, 10 h, 2.) MeOH, RT, 4h; Yield given; |
4-aminobutyraldehyde dimethyl acetal
4-methoxyphenylhydrazine hydrochloride
acetic anhydride
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
1.) 5 - 10 deg C, 1 h, 2.) AcOH, EtOH, H2O, 40 deg C, 12 h; Yield given; Multistep reaction; |
Conditions | Yield |
---|---|
With sheep pineal supernatant (serotonin-N-acetyl transferase); Pargyline In phosphate buffer at 37℃; for 0.166667h; pH=6.8; Enzyme kinetics; |
Conditions | Yield |
---|---|
Stage #1: acetic anhydride; 3-(2-isocyanato-ethyl)-5-methoxy-1H-indole In acetic acid Heating; Stage #2: With potassium carbonate In methanol at 20℃; Further stages.; |
Conditions | Yield |
---|---|
In acetic acid Heating; Title compound not separated from byproducts.; |
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With Tris-HCl buffer In ethanol; water at 37℃; pH=7.40; Kinetics; Further Variations:; pH-values; Reagents; Solvents; | |
With Tris-HCl buffer; L-Cysteine In ethanol; water at 37℃; pH=7.40; Kinetics; Further Variations:; pH-values; Reagents; |
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With perchloric acid; d(4)-methanol at 75℃; for 24h; Inert atmosphere; | 100% |
With tris(pentafluorophenyl)borate; water-d2 In chloroform-d1 at 80℃; for 24h; Sealed tube; regioselective reaction; | 95% |
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With Iodine monochloride In dichloromethane at 20℃; for 8h; Inert atmosphere; | 98% |
With chloroamine-T; potassium iodide In chloroform for 0.0833333h; | 87% |
With iodine; silver trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 0.333333h; | 46% |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 120℃; for 20h; Inert atmosphere; | 98% |
di-tert-butyl dicarbonate
5-methoxy-N-acetyl-tryptamine
N-[2-(1-tert-butoxycarbonyl-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Conditions | Yield |
---|---|
With dmap In acetonitrile at 25℃; for 16h; | 95% |
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 0℃; for 0.5h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 0℃; for 1h; Further stages.; | 80% |
With dmap In tetrahydrofuran | 70% |
Stage #1: 5-methoxy-N-acetyl-tryptamine With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 5h; Inert atmosphere; | 1.13 g |
N-(phenylthio)succinimide
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With 2-((-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)cyclohexyl)carbamoyl)-3,4,5,6-tetrachlorobenzoic acid; trifluoroacetic acid In methanol; dichloromethane; water at 20℃; for 24h; | 95% |
5-methoxy-N-acetyl-tryptamine
chloroformic acid ethyl ester
3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 20℃; for 1h; | 93% |
Conditions | Yield |
---|---|
With palladium diacetate; silver carbonate In 1,4-dioxane at 80℃; for 10h; Schlenk technique; Inert atmosphere; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
In water at 20℃; for 94h; Formylation; | 92% |
Acylation; | 88% |
5-methoxy-N-acetyl-tryptamine
acetic anhydride
Nb,Nb-diacetyl-5-methoxytryptamine
Conditions | Yield |
---|---|
for 2h; Acetylation; Heating; | 92% |
Conditions | Yield |
---|---|
With C9H18NO(1+)*BH4(1-) In tetrahydrofuran at 0℃; | 92% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 3h; Condensation; | 91% |
5-methoxy-N-acetyl-tryptamine
p-toluenesulfonyl chloride
N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide
Conditions | Yield |
---|---|
Stage #1: 5-methoxy-N-acetyl-tryptamine With tetrabutylammomium bromide; sodium hydroxide In dichloromethane at 20℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 6h; | 90.5% |
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃; | |
Stage #1: 5-methoxy-N-acetyl-tryptamine With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 5h; Inert atmosphere; | 1.20 g |
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In dichloromethane at 0 - 20℃; |
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With sodium hydroxide; [131I]-sodium iodide; chloroamine-T In chloroform for 0.05h; | 90% |
Conditions | Yield |
---|---|
With tris(bipyridine)ruthenium(II) dichloride hexahydrate In methanol; dichloromethane; water Sealed tube; Irradiation; Cooling with ice; regioselective reaction; | 90% |
5-methoxy-N-acetyl-tryptamine
trifluoroacetic anhydride
Trifluoro-acetic acid (2S,3'S)-5-methoxy-2'-methylene-1,1'-bis-(2,2,2-trifluoro-acetyl)-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-2-yl ester
Conditions | Yield |
---|---|
In benzene at 5℃; for 0.166667h; | 89% |
Conditions | Yield |
---|---|
With ammonium bromide; ethylenediamine at 100℃; for 7h; Microwave irradiation; | 89% |
With sulfuric acid In water for 8h; Heating; | 69.7% |
With sodium hydroxide In 2-methyl-propan-1-ol |
5-methoxy-N-acetyl-tryptamine
benzenesulfonyl chloride
N-[2-(1-benzenesulfonyl-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Conditions | Yield |
---|---|
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 0℃; for 0.5h; Stage #2: benzenesulfonyl chloride In dichloromethane at 0℃; for 1h; Further stages.; | 88% |
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium hydroxide; tetra-(n-butyl)ammonium iodide at 0℃; for 0.25h; Stage #2: benzenesulfonyl chloride at 20℃; for 3.5h; | 71% |
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.166667h; chemoselective reaction; | 88% |
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.166667h; | 88% |
5-methoxy-N-acetyl-tryptamine
4-methoxy-3-(4-(2,2,2-trichloro-acetyl)piperazin-1-yl)benzene-1-sulfonylchloride
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2.16h; | 88% |
5-methoxy-N-acetyl-tryptamine
O,O'-bis[(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]-hept-3-yl]dithiophosphoric acid
Conditions | Yield |
---|---|
In ethanol at 20℃; for 1h; Inert atmosphere; | 88% |
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
In ethanol at 20℃; for 2h; Inert atmosphere; | 87% |
Melatonin (CAS NO.73-31-4) is related to the mechanism by which some amphibians and reptiles change the color of their skin and, indeed, it was in this connection the substance first was discovered. McCord and Allen discovered (J Exptl Zool, 1917) that extract of the pineal glands of cows lightened frog skin, while Aaron B. Lerner is credited for naming the hormone and for defining its chemical structure in 1958. In the mid-70s Lynch et al. demonstrated that also in humans the production of melatonin exhibits a circadian rhythm.
1. Introduction of Melatonine
Melatonine is one kind of white or off-white powder. The IUPAC name of this chemical is N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide. Besides, Melatonine belongs to Heterocyclic Series; Heterocycles series; Indoles; Tryptamines; Nutritional Supplements; Intermediates & Fine Chemicals; Pharmaceuticals; Melatonin receptor. In addition, Melatonine Classification Code is Antioxidants; Central Nervous System Agents; Central Nervous System Depressants; Drug / Therapeutic Agent; Hormone; Mutation data; Protective Agents; Reproductive Effect; Tumor data.
What's more, Melatonine solubility in water is soluble0.1 mg/mL, in ethanol is soluble8 mg/mL. It is a naturally occurring hormone found in animals and in some other living organisms, including algae.
2. Properties of Melatonine
Physical properties about Melatonine are:
(1)Melting point: 116.5-118 °C(lit.); (2)Density: 1.175 g/cm3; (3)Flash Point: 264 °C ; (4)storage temp.: -15 °C; (5)Index of Refraction: 1.6; (6)Surface Tension: 46.6 dyne/cm; (7)Enthalpy of Vaporization: 78.41 kJ/mol; (8)Boiling Point: 512.8 °C at 760 mmHg; (9)Vapour Pressure: 1.25E-10 mmHg at 25 °C; (10)XLogP3: 0.8; (11)H-Bond Donor: 2; (12)H-Bond Acceptor: 2.
3. Structure Descriptors of Melatonine
(1)Canonical SMILES: CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC
(2)InChI: InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
(3)InChIKey: DRLFMBDRBRZALE-UHFFFAOYSA-N
(4)Smiles: c12c([nH]cc1CCNC(C)=O)ccc(c2)OC
4. Toxicity of Melatonine
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 1375mg/kg (1375mg/kg) | Pharmaceutical Chemistry Journal Vol. 17, Pg. 559, 1983. | |
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02739, | |
mouse | LD50 | oral | 1250mg/kg (1250mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983. | |
mouse | LD50 | subcutaneous | > 1600mg/kg (1600mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983. | |
rat | LD50 | intraperitoneal | 1131mg/kg (1131mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983. | |
rat | LD50 | intravenous | 356mg/kg (356mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983. | |
rat | LD50 | oral | > 3200mg/kg (3200mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983. | |
rat | LD50 | subcutaneous | > 1600mg/kg (1600mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983. |
Melatonin (CAS NO.73-31-4) has a very low toxicity in rats. Rat maternal toxicity: the no observable adverse effect level (NOAEL) and lowest observed adverse effect level (LOAEL) were 100 and 200 mg/kg/day, respectively, and the developmental toxicity NOAEL was >= 200 mg/kg/day.
5. Safety information of Melatonine
Hazard Codes: T
Risk Statements: 60
R60: May impair fertility.
Safety Statements: 24/25
S24/25: Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: AC5955000
F: 8-10-23
6. Uses of Melatonine
Melatonin (CAS NO.73-31-4) is important in the regulation of the circadian rhythms of several biological functions.The primary motivation for the use of melatonin as a supplement may be as a natural aid to better sleep. Many biological effects of melatonin are produced through activation of melatonin receptors, while others are due to its role as a pervasive and powerful antioxidant with a particular role in the protection of nuclear and mitochondrial DNA. Melatonin have been available as a dietary supplement.
Several clinical studies indicate that supplementation with melatonin is an effective preventive treatment for migraines and cluster headaches. It has been shown to be effective in treating one form of depression, seasonal affective disorder, and is being considered for bipolar and other disorders where circadian disturbances are involved. Melatonin is involved in the regulation of body weight, and may be helpful in treating obesity. Histologically, it is believed that melatonin has some effects for sexual development in higher organisms.
7. Production of Melatonin
Melatonin present in the pineal gland of the mammalian brain, the general method of the bovine brain pineal freeze-dried and pulverized into a powder, with petroleum ether and removal of fat, uniformly mixed into a slurry with deionized water, forafter centrifugation, the supernatant was taken with an equal volume of ethyl acetate extract, and the extract was dried in vacuo to give a white crude melatonin Collectibles then obtained after recrystallization.
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