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A hormone secreted by the pineal gland cells Pineal Pineal hormone synthesis and release Physiological effects of pineal gland Chemical properties Uses

CAS No. 73-31-4
Chemical Name: Melatonine
Synonyms: MLT;MLK7;MLT1;primex;mlklak;Circadin;Melovine;MELATONIN;melotonin;MELATONINE
CBNumber: CB5364927
Molecular Formula: C13H16N2O2
Formula Weight: 232.28
MOL File: 73-31-4.mol
Melatonine Property
Melting point : 116.5-118 °C(lit.)
Fp : 9℃
storage temp. : -15°C
solubility : Soluble in ethanol to at least 50mg/ml
Merck : 5816
CAS DataBase Reference: 73-31-4(CAS DataBase Reference)
NIST Chemistry Reference: Melatonin(73-31-4)
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes : T,F
Risk Statements : 60-39/23/24/25-23/24/25-11
Safety Statements : 24/25-99-53-45-36/37-16-7
WGK Germany : 2
RTECS : AC5955000
F : 8-10-23
HS Code : 29379000
Hazardous Substances Data: 73-31-4(Hazardous Substances Data)
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
Precautionary statements:
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P311 Call a POISON CENTER or doctor/physician.
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

Melatonine Chemical Properties,Usage,Production

A hormone secreted by the pineal gland cells
Melatonin is a hormone secreted by the pineal gland, and its chemical structure was 5-methoxy-N-acetyl tryptamine, the physiological function of inhibiting gonad, thyroid, adrenal gland, parathyroid gland and pituitary function, inhibit precocious puberty, reduce pituitary Melanotropin secretion; and has a central nervous system function, can improve the convulsion the threshold, cause drowsiness. When pinealectomy after the animal experiment showed hyperplasia of the glands, weight increase, especially sex and sexual organs of immature rats early, pituitary secretion of LH and FSH increased, increasing secretion of thyroid and adrenal cortex hormone melatonin. More reduced pituitary MSH and whiten the skin of this role. Effects on the central nervous system, in the human EEG showed slow rhythm, increased seizure threshold, sleepiness, but does not affect their behavior and personality, of temporal lobe epilepsy and Ba Jinsen disease can reduce the motor nerve Abnormal EEG changes.
Pineal gland is shaped like pinecones, about 7mm long , 5mm wide and 4mm thick, and the weight is about 140~200mg. Epiphysis is located above the superior colliculus of midbrain behind which there is the great cerebral vein. Pineal body is covered by corpus callosum from back. Pineal is stem from ependyma in the third ventricle of cerebrum during embryonic period, from where this sector sticks out and forms the pineal gland. Most parts of pineal are wrapped by pia mater. The connective tissue of the mantle extends inward, dividing the pineal into irregular leaflets. Postganglionic fibers of superior cervical sympathetic ganglion enter into pineal gland with blood vessel. Pineal body is composed of vast pineal cells and a small amount of gliocyte. Pineal cells are polygon, long cylindrical or oval. Usually, the cytoplasmic processes are of different lengths; the cytoplasm is basophilic, often containing lipoid droplets. The nucleuses of pineal cells are large and have nucleoli, presenting irregular sags or lobulated shapes. Under the electron microscope, we can see developed golgi complex, abundant rough endoplasmic reticulum, free ribosome and lysosome, a large number of microtubules and secretory granules vesicles in the cytoplasm. Vesicles also appear in the cell process which containing norepinephrine, dopamine, 5-hydroxytryptamine and melatonin and so on. Gliocyte is also erumpent, and its nucleus is also oval. Both nucleus and cytoplasm are stained darker. We can also see rough endoplasmic reticulum, free ribosome, rich microfilament in the cytoplasm under the electron microscope, which can be distinguished from the pineal cell. There are also many solidified bodies in the pineal gland, which contain hydroxylapatite and calcium carbonate apatite and form small mulberry shaped pieces named brain sand whose size and number increase with age.
The above information is edited by the Chemicalbook Bai Linlin.
Pineal hormone synthesis and release
Pineal cells obtain tryptophan from blood circulation and become 5-hydroxytryptophane catalyzed by hydroxylase and 5-hydroxytryptophane turns into 5-hydroxytryptamine after decarboxylated by decarboxylase. There are three possible changes for 5-hydroxytryptamine: for the first part it may turn into 5-hydroxyl-benzpyrole acetic acid when deaminated by monoamine oxidase; for another part, some 5-hydroxytryptamine will leave the pineal cell and be taken in by sympathetic nerve ending and stored with neurotransmitter and noradrenalin; for the remaining part, the 5-hydroxytryptamine will be acetylated by N-acetyl-5-hydroxy tryptamine transferase and then be o-methoxy by hydroxylation indole-o-methyl converzyme, finally forming melatonin. After being synthesized, melatonin will be released by cells and enter into blood circulation through cerebrospinal fluid or directly, where noradrenalin may strengthen the synthesis, the speed of which depends on activity of hydroxylase in liver microsomes. Catalyzed by the hydroxylase, 6-hydroxylmelatonin is formed, soon afterwards it combines with glucuronic acid and sulfate, excreting through urine.
Physiological effects of pineal gland
1. The effect to brain: the melatonin obtained by brain mainly gathers in midbrain and hypothalamus and it adds the activity of brain pyridoxal kinase, thus promoting glutamic acid decarboxylation to γ-amino butyric acid, 5-hydroxytryptophane decarboxylation to 5-hydroxytryptamine, both of which can inhibit the increase of the neurotransmitter content and have an effect of adjustment and mitigation on central nervous system.
2. The effect to hypothalamus and pituitary: materials like polypeptide produced by pineal body still have thyrotropin-releasing hormone(TRH) and luteinizing hormone releasing hormone(LRH) which are same with what hypothalamus produces except AVT. After injection of melatonin, gonadotropin (GnH)(FSH、LH) and melanocyte stimulating hormone(MSH) are lowered while growth hormone increases. Cutting pineal gland will cause pituitary hypertrophy, increase pituitary secretion and lower prolactin(PRL) and antidiuretic hormone (ADH).
3. The relation to gonad: melatonin has an inhibitory effect on the reproductive system. Clinically, main cytoma of pineal body can lead to pubertal delay and when teratoma appears in pineal body, it may result in sexual precocity because main cells are excluded. Ambient light and sympathetic nerve can affect the function of the reproductive system by inhibiting the synthesis and release of melatonin in pineal gland.
4. The relation to thyroid: by injecting melatonin, thyroid secretion will decrease. This may be caused through the inhibition of the hypothalamus release and Thyroid Stimulating Hormone (TSH) secretion of pituitary, hence holding back the function of thyroid.
5. The relation to adrenal cortex: melatonin has a strong inhibitory effect on adrenal cortex. If we inject pineal body extracts to healthy people, we will find that their aldosterone secretion and 17-ketosteroid output will decrease.
6. The relation to pancreatic island: melatonin can lower blood glucose and increase sugar tolerance. In conclusion, pineal gland can assist pituitary to jointly adjust endocrine function and play an vital role in keeping relatively constant in body environment and controlling some endocrine function, especially for gonad.
Chemical properties
White or almost white crystalline powder.
1. Melatonin can be used as medicine health care products, so as to enhance people’s immune function, preventing aging and back to youth. What’s more, it is also a kind of natural “sleeping pill”.
2. Melatonin is a kind of hormone secreted by pineal body of pituitary gland in the body. The amount of melatonin has something to do with light. The weaker the light is, the more the melatonin is, whereas the less. In addition, it is helpful to one’s sleep.
3. Biochemical research.
Chemical Properties
Off-White Powder
Hormone postulated to mediate photoperiodicity in mammals. Inhibits cerebellar nitric oxide synthetase
sleep induction, modifies circadian rhythm, antioxidant, free radical scavenger
Immunostimulant;Melatonin receptor ligand
Hormone; mediates photoperiodicity in mammals; inhibits cerebellar nitric oxide synthetase; peroxynitrite scavenger. Melatonin has complex effects on apoptotic pathways, inhibiting apoptosis in immune cells and neurons but enhancing apoptotic cell death of cancer cells. Inhibits proliferation/metastasis of breast cancer cells by inhibiting estrogen receptor action.
ChEBI: A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen atom is replaced by a 2-(5-methoxy-1H-indol-3-yl)ethyl group. It is a hormone secreted by the pineal gland in humans.
Biological Activity
Endogenous hormone that acts as an agonist at melatonin receptors MT 1 and MT 2 . Exhibits a prominent role in the control of circadian rhythm, displays immunomodulatory activity and acts as a powerful antioxidant in vivo .
Melatonine Preparation Products And Raw materials
Raw materials
Preparation Products
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73-31-4(Melatonine)Related Search:
2-(2-Aminoethylamino)ethanol 2,4-Pentanedione Acetyl chloride Ethyl formate 3-Methoxybenzaldehyde Ethyl acetate Etanol Acetamide Ethyl propionate 4'-Methoxyacetophenone Ethyl acrylate Anisic aldehyde Diethyl ether (Trifluoromethoxy)benzene p-Anisidine Ethylenzene N-ACETYL-L-TYROSINE ETHYL ESTER Tetraacetylethylenediamine
Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]- Acetamide, N-[2-(5-methoxyindol-3-yl)ethyl]- Acetamide,N-[2-(5-methoxy-1H-indol-3-yl)ethyl] Melatonin(N-Acetyl-5-methoxytryptamine) n-(2-(5-methoxy-1h-indol-3-yl)ethyl)-acetamid n-(2-(5-methoxyindol-3-yl)ethyl)-acetamid Indoles Tryptamines N-ACETYL-5-METHOXYTRYPTAMINE N-[2-(5-METHOXY-1H-INDOL-3-YL)ETHYL]ACETAMIDE N-(2-(5-methoxyindol-3-yl)ethyl)acetamide MLT Nitric Oxide Synthase Heterocyclic Building Blocks Enzymes, Inhibitors, and Substrates Enzyme Inhibitors by Enzyme Enzyme Inhibitors L to O TIMTEC-BB SBB003265 MELATONINE MELATONIN 3-(N-ACETYL-2-AMINOETHYL)-5-METHOXYINDOLE 73-31-4 5-METHOXY-N-ACETYLTRYPTAMINE ACETYL-5-METHOXYTRYPTAMINE AKOS BB-4935 Biochemicals and Reagents Building Blocks BioChemical 3-N-Acetyl-5-methoxyl tryptamine Hormone; mediates photoperiodicity in mammals; inhibits cerebellar nitric oxide synthetase; peroxynitrite scavenger. MELATONIN, 99.5+% MELATONIN F&D VERSION FOR VETERINARY US MELATONIN CRYSTALLINE MELATONIN,(SECONDARY STANDARD) MELATONIN,(PRIMARY STANDARD) MELATONIN, HPLC ANALYSIS KIT MELATONIN,1.0MG/MLINMETHANOL MELATONIN,POWDER N-[2-(5-methoxy-1H-indol-3-yl)ethyl]ethanamide MELATONIN (MLT) primex Heterocyclic Series N-Acetyl-5-Methoxytryptamine also Melatonine pharmaceutical grade Melatonin Heterocycles series Melatonin 99.0%min Indoles Tryptamines Nutritional Supplements Intermediates & Fine Chemicals Pharmaceuticals Circadin Melovine Melatonin ,99% Melatonin receptor 3-[2-(Acetylamino)ethyl]-5-methoxy-1H-indole N-Acetyl-5-methoxytriptamine
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