Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)-
Melatonine
CAS: 73-31-4;8041-44-9
Molecular Formula: C13H16N2O2
Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)- - Names and Identifiers
| Name | Melatonine |
| Synonyms | MLT Melatonin Melatonine L-Arabinitol Melatonin (AS) Melatonin solution MELATONINE FOR SYNTHESIS 5 G MELATONINE FOR SYNTHESIS 1 G N-Acetyl-5-methoxytryptamine 3-N-Acetyl-5-methoxyl tryptamine Melatonin N-Acetyl-5-methoxytryptamine N-(2-(5-methoxyindol-3-yl)ethyl)acetamide Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)- N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide N-[2-(5-METHOXY-1H-INDOL-3-YL)ETHYL]ACETAMIDE Melatonine,N-(2-(5-Methoxyindol-3-yl)ethyl)acetaMide |
| CAS | 73-31-4 8041-44-9 |
| EINECS | 200-797-7 |
| InChI | InChI=1/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) |
| InChIKey | DRLFMBDRBRZALE-UHFFFAOYSA-N |
Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)- - Physico-chemical Properties
| Molecular Formula | C13H16N2O2 |
| Molar Mass | 232.28 |
| Density | 1.1099 (rough estimate) |
| Melting Point | 116.5-118 °C (lit.) |
| Boling Point | 374.44°C (rough estimate) |
| Flash Point | 9℃ |
| Solubility | DMSO : 100 mg/mL (430.51 mM; Need ultrasonic);Ethanol : ≥ 50 mg/mL (215.26 mM) |
| Vapor Presure | 1.25E-10mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | white to off-white |
| Merck | 14,5816 |
| BRN | 205542 |
| pKa | 16.26±0.46(Predicted) |
| Storage Condition | -20°C |
| Sensitive | `sensitive` to light, easy to oxidize |
| Refractive Index | 1.6450 (estimate) |
| MDL | MFCD00005655 |
| Physical and Chemical Properties | white or off-white crystalline powder |
| Use | Used in medicine and health care products, can enhance the body's immune function, prevent aging return to youth, and is a natural "sleeping pill". |
Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)- - Risk and Safety
| Risk Codes | R60 - May impair fertility R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S99 - S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. |
| UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 2 |
| RTECS | AC5955000 |
| FLUKA BRAND F CODES | 8-10-23 |
| HS Code | 29379000 |
| Toxicity | LD50 orally in Rabbit: > 3200 mg/kg |
Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)- - Reference
| Reference Show more | 1. Xu Shuo, Jin, Peng, Fei, Yong Mei, Xu, Wenfeng, Wu, Xuejun, Jiang, Wenqing. Determination of 10 sedative and hypnotic drugs illegally added in traditional Chinese medicines and health products by HPLC [J]. Northwest Pharmaceutical Journal, 2019, 34(02):181-185. 2. Shen Guohua, Dong Peizhi, Pei Shiqiang. Uncertainty Analysis of melatonin content in health food by HPLC [J]. Bright light Chinese Medicine 2013(05):918-920. 3. Zhao Xiaohong, Luo Qingxi, Rao Ling. Effects of exogenous melatonin on chilling resistance of cucumber seedlings under low temperature stress [J]. Northern horticulture, 2017, 38 (14):55-59. 4. Li Qing, Wang Jieyu, Zhang Xiaodan, etc. Drug efficacy and pain mechanism in mice with adenomyosis [J]. Chinese Journal of Laboratory Animal Science, 2016, 24(005):516-520. 5. Xin Bing Xu, Chenglin Li, Zhiguo Liu, et al. Melatonin attenuates oxidative damage in lung tissue of dynamic inhalation of rocket kerosene mice [J]. Chinese electronic journal of health emergency, 2015, 26 (2):19-21. 6. Deng Yu, Mi Chao, Li Lehui, etc. Effects of melatonin on manganese-induced dyskinesia and striatal injury in mice [J]. Chinese Journal of Industrial Medicine, 2013, 30 (6):403-405. 7. Xu Donghui, Deng Yu, Li, Lehui, et al. Effects of melatonin-activated Nrf2 and HO-1 on manganese-induced oxidative stress in striatum [J]. Journal of Toxicology, 2013, 027(004):39-43. 8. Zhang Tingting, Li Yongcai, Bi Yang, etc. Effect of melatonin on ripening of apricot fruit [J]. China fruit tree, 2019, 000(001):27-31. 9. Xu Shuo, Xu Wenfeng, Jin Pengfei, Wu Xuejun, Jiang Wenqing. Simultaneous determination of vitamin B _6 and melatonin in compound melatonin tablets by HPLC [J]. China medical review, 2017,14(03):142-146. 10. Shi Xinjing, Wang Xianghong, Jin Na, et al. Effects of melatonin on fruit quality of delayed cultivation of 'red globe 'Grape [J]. China fruit tree, 2020, No.202(02):46-50. 11. Qiao Pei, Yin Fei Yu, Wang Yu Xuan, Li Jing, Dong Xinhong. Effects of exogenous melatonin on Browning and active oxygen metabolism of postharvest litchi [J]. Science and Technology of food industry, 2021,42(06):282-287. 12. Huang, he. Effects of 5-hydroxytryptamine and melatonin on improving low temperature tolerance of rapeseed [D]. Chinese Academy of Agricultural Sciences, 2020. 13. Zhipin Wang, Hong Jiang, Xujiao Chen, Xinhua Song, Fengjing Xu, Fangchao Chen, Zhigu Mao, Shouhong Gao, Wansheng Chen,A rapid and sensitive method for simultaneous determination of eight protein-bound uremic toxins in human serum by UHPLC-MS/MS: applica 14. Zhen Yang, Mingji Li, Hongji Li, Huayi Li, Cuiping Li, Baohe Yang, Polycrystalline boron-doped diamond-based electrochemical biosensor for simultaneous detection of dopamine and melatonin, Analytica Chimica Acta, Volume 1135 2020, Pages 73-82, ISSN 0003-2 15. [IF=5.537] Hui Gao et al."Melatonin treatment delays postharvest senescence and regulates reactive oxygen species metabolism in peach fruit."Postharvest Biol Tec. 2016 Aug;118:103 16. [IF=4.486] Hai-ru Li et al."Melatonin attenuates doxorubicin‐induced cardiotoxicity through preservation of YAP expression."J Cell Mol Med. 2020 Mar;24(6):3634-3646 17. [IF=3.935] Zhipeng Wang et al."A rapid and sensitive method for simultaneous determination of eight protein-bound uremic toxins in human serum by UHPLC-MS/MS: application in assessing peritoneal dialysis."J Pharmaceut Biomed. 2020 Jul;186:113312 18. [IF=2.247] Peng Tian et al."Transcriptomics analysis of genes induced by melatonin related to glucosinolates synthesis in broccoli hairy roots."Plant Signal Behav. 2021;16(11):1952742 19. [IF=2.19] Shuangfeng Guo et al."Melatonin and 1-methylcyclopropene treatments on delay senescence of apricots during postharvest cold storage by enhancing antioxidant system activity."J Food Process Pres. 2021 Oct;45(10):e15863 |
Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)- - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| Introduction | melatonin is an indispensable natural hormone in human body, which controls and affects the secretion of other different hormones. When melatonin is reduced in the body, various functions of the human body will be affected, and various diseases will follow. Studies have shown that the secretion of melatonin in the human body began to decrease after middle age, and the amount of its secretion has been slightly low. Early Intake of melatonin supplement enough, can improve the function of the endocrine system, improve immunity, improve anti Nervousness, antioxidant function, improve sleep, slow down the aging rate of the human body, slow down the rate of degeneration of sexual organs; melatonin can also help prevent and treat cancer, especially for habitual Sleep Initiation and Maintenance Disorders. |
| Use | melatonin is a hormone produced by the pineal gland. Melatonin is a highly conserved, Non-receptor free radical scavenger and broad-spectrum antioxidant. Melatonin helps prevent ischemia-reperfusion injury to the liver, brain, heart muscle, intestine and kidney. Melatonin can be widely used in health food, medicine, all kinds of cosmetics, nourishing and nursing products. function: 1. Melting and removing freckle, natural whitening: melatonin can whiten skin. Can regulate the body's endocrine, get rid of dark spots, age spots, melasma, pregnancy spots and pigmentation caused by sun radiation, skin whitening, moisturizing, restore the youth style. 2. Effective sleep improvement: appropriate melatonin supplementation can effectively improve sleep quality. 3. Longevity:. Melatonin is the most important endogenous antioxidant in the brain, which has a protective effect on the brain. Therefore, melatonin is an important anti-aging hormone. 4. Maintenance and enhancement of sexual function: melatonin supplementation can make aging body failure, energy decline and lead to loss of libido in the elderly to improve sexual function. used in medicine and health care products, can enhance the body's immune function, prevent aging return to youth, and is a natural "sleeping pill". It is a hormone secreted by the pineal body of the pituitary gland in the body. The amount of this hormone is related to light, less to help sleep. biochemical studies Melatonin has complex effects on apotative pathways, inhibiting apotosis in immune cells and Neurot but Hanning apottic cell death of cancer cells. Inhibitors of breast cancer cells by inhibition. used in medicine and health products, can enhance the body's immune function, and is a natural "sleeping pill" |
| a hormone secreted by pineal cells | melatonin, also known as melatonin, is a hormone secreted by pineal cells, its chemical structure is 5-methoxy-n-acetyltryptamine. Its physiological function is to inhibit gonad, thyroid, adrenal gland, parathyroid and pituitary function, inhibit precocious puberty in children and reduce pituitary melanin secretion; and has the role of the central nervous system, can increase the threshold of convulsions, causing drowsiness. When the pineal gland was removed, the experimental animals showed hyperplasia and hypertrophy of the aforementioned glands, increased weight, especially the precocious gonads and sexual organs of immature rats, and increased secretion of LH and FSH by the pituitary gland, thyroid and adrenal cortical hormone secretion increased. Pineal hormone has the effect of reducing the pituitary MSH and whitening the skin. This hormone acts on the central nervous system, shows a slow rhythm in the human EEG, increases the seizure threshold, drowsiness, but does not affect its behavior and character, EEG changes in patients with temporal lobe epilepsy and Parkinson's disease can reduce the motor nerve disorders. |
| pineal gland | The pineal gland is shaped like a pineal gland, about 7mm in length, 5mm in width, 4mm in thickness, 140 ~ 200mg in weight, it is located above the superior colliculus of the midbrain, followed by the great cerebral vein, which is covered by the posterior part of the corpus callosum. It originates from the ependymal membrane at the top of the third ventricle in the embryonic stage, and thus it is formed by upward protrusion. Most of it is surrounded by the pia mater, the soft membrane of the connective tissue into the pineal gland to separate into irregular lobules. The retroganglionic fibers of the superior cervical ganglion of the sympathetic nerve enter the pineal gland along with the blood vessels. The pineal gland is composed of a large number of pineal cells and a small number of glial cells. The pineal cells are polygonal, cylindrical or oval in shape, with different cell lengths and basophilic cytoplasm, often containing lipid droplets, large nuclei, irregular concave or lobulated, with nucleoli. Under the electron microscope, the Golgi complex was developed in the cytoplasm, and the rough endoplasmic reticulum was rich in free nucleosomes, lysosomes, as well as a large number of microtubules and Secretory granule vesicles, which also appeared in the cytoplasm, vesicles contain norepinephrine, dopamine, serotonin and pineal hormone, also known as melatonin. Glial cells also have processes, nuclear Oval, nuclear and cytoplasmic staining were deeper, the cytoplasm also has rough endoplasmic reticulum, free nuclear protein body, it can be distinguished from pineal cells by being rich in microfilaments. A large amount of coagulated body was also found in the pineal gland, containing hydroxyapatite and calcium carbonate apatite, Often formed into Mulberry-like small pieces, called brain sand, its size and number increase with age. |
| synthesis and release of pineal hormone | the uptake of tryptophan by pineal cells from blood circulation is changed to 5-hydroxytryptophan under the catalysis of hydroxylase, the latter are decarboxylated to serotonin by a decarboxylase, and there are three possible transformations of serotonin: one part is deaminated by monoamine oxidase into 5-hydroxy-indoleacetic acid; The other part leaves the pineal cells, taken up by sympathetic nerve endings and stored together with the neurotransmitter norepinephrine; The third part is acetylated by N-acetyl serotonin transferase, then it is o-methoxylated by hydroxylated indole-o-methyl-converting enzyme to form melatonin. After melatonin is synthesized, it may be released by cells into the blood circulation or through cerebrospinal fluid into the blood circulation. Norepinephrine can strengthen its synthesis, and its speed depends on the activity of hydroxylase in liver cells microsomes, this enzyme catalyzes the formation of 6-hydroxymelatonin, which is subsequently combined with glucuronic acid and sulfate and excreted in urine. |
| physiological function of pineal gland | ① effect on brain: melatonin uptake by brain is concentrated in midbrain and hypothalamus, it enhances the activity of brain pyridoxal kinase, thereby promoting the decarboxylation of glutamate to form gamma-aminobutyric acid, the decarboxylation of serotonin to form serotonin, the increase in the content of these two inhibitory neurotransmitters, it has a regulating and sedative effect on the central nervous system. ② effects on hypothalamus and pituitary: The polypeptides produced by the pineal gland include, in addition to AVT, thyrotropin-releasing hormone (TRH) and luteinizing hormone-releasing hormone (LRH), the same as produced by the hypothalamus. After melatonin injection, gonadotropin (GnH) (FSH, LH) and melanocyte stimulating hormone (MSH) decreased, while growth hormone (GH) increased. Removal of the pineal gland results in pituitary hypertrophy, increased secretion of pituitary GnH (FSH, LH) and ACTH, and decreased prolactin (PRL) and antidiuretic hormone (ADH). ③ relationship with gonads: pineal hormone has an inhibitory effect on the reproductive system. Clinically, pineal principal cell tumor can lead to delayed puberty, while pineal teratoma, because the main cells are excluded, may be complicated by precocious puberty. Environmental light and sympathetic nerve can affect the function of reproductive system by controlling the synthesis and release of melatonin in pineal gland. ④ relationship with thyroid: When melatonin is given, the secretion of thyroid hormone decreases, probably by inhibiting the release of TRH from hypothalamus and the secretion of TSH from pituitary gland, thereby inhibiting thyroid function. (5) the relationship between melatonin and adrenal cortex: melatonin has a strong inhibitory effect on the adrenal cortex. When pineal extract was injected into healthy people, the secretion of aldosterone decreased and the output of 17 ketosterols decreased. (6) relationship with pancreatic islets: pineal hormone can lead to decreased blood glucose and increased glucose tolerance. In summary, the pineal gland can assist the pituitary gland to regulate endocrine function, to maintain the internal environment of the body is relatively constant, control some endocrine function, especially to the gonad has an important role. |
| production method | 1. Melatonin is present in the pineal gland of the mammalian brain. In general, the pineal gland of the bovine brain is freeze-dried and ground into a powder. The fat is removed with petroleum ether and mixed with deionized water to form a slurry, after centrifugation, the supernatant was taken and extracted with an equal volume of ethyl acetate. The extract was dried under vacuum to obtain a white melatonin crude product, and then recrystallized to obtain a fine product. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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