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73-31-4

Basic Information
CAS No.: 73-31-4
Name: Melatonine
Article Data: 68
Molecular Structure:
Molecular Structure of 73-31-4 (Melatonine)
Formula: C13H16N2O2
Molecular Weight: 232.282
Synonyms: N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide;N-Acetyl-5-methoxytryptamine;5-Methoxy-N-acetyltryptamine;Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)-;acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-;N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide;Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]- (6CI,8CI);Melovine;Acetamide, N-[2- (5-methoxy-1H-indol-3-yl)ethyl]-;Melatonin;Acetamide, {N-[2-(5-methoxyindol-3-yl)ethyl]-};Circadin;Acetamide,N-[2-(5-methoxy-1H-indol-3-yl)- ethyl]-;Prestwick_312;Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]- (9CI);Melatonin (MLT);
EINECS: 200-797-7
Density: 1.175 g/cm3
Melting Point: 116.5-118 °C(lit.)
Boiling Point: 512.831 °C at 760 mmHg
Flash Point: 263.951 °C
Appearance: Off-white powder
Hazard Symbols: ToxicT
Risk Codes: 60
Safety: 24/25-99-53-45
PSA: 54.12000
LogP: 2.24600
Synthetic route
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

108-24-7

acetic anhydride

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With pyridine In dichloromethane100%
In 1,2-dichloro-ethane at 0℃; for 1h;96%
With triethylamine95%
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

75-36-5

acetyl chloride

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In dichloromethane at 25 - 30℃; Temperature;98.3%
With triethylamine In dichloromethane at 20℃;
With triethylamine In dichloromethane at 0 - 20℃; for 5h;
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

10387-40-3

potassium thioacetate

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In ethyl acetate at 20℃; Electrochemical reaction;97%
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

2735-73-1

1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.3h;93%

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

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With ammonia; sodium In tetrahydrofuran at -78 - -33℃; for 1h;92%
108-05-4

vinyl acetate

608-07-1

2-(5-methoxyindol-3-yl)ethylamine

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
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%
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

507-09-5

thioacetic acid

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation;92%
1020701-51-2

N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
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%
66-83-1

5-methoxytryptamine hydrochloride

108-24-7

acetic anhydride

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 3h;90%
16045-88-8, 373-57-9

boron trifluoride methanol complex

136788-90-4

Nb-acetyl-1-hydroxytriptamine

73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In methanol Heating;80%
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History

  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.

Specification

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: Toxic
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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