CAS 73-31-4 MFCD00005655-N-Acetyl-5-methoxytryptamine 褪黑素 TAO{mole}

N-Acetyl-5-methoxytryptamine 褪黑素

CAS 73-31-4 MFCD00005655

化学结构图

SMILES: COc1ccc2[nH]cc(CCNC(C)=O)c2c1

化学属性

Mol. Formula	C13H16N2O2
Mol. Weight	232.28
Density	1.422
Melting Point	116.5-118°C
Stability	对光线敏感，易氧化
Appearance	白色或类白色结晶粉末
Boiling Point	512.8°C at 760 mmHg

别名和识别编码

Chemical Name	N-Acetyl-5-methoxytryptamine
CAS Number	73-31-4
Synonym	Melatonin {LY} Melatonin {} {LY} Melatonin {} {} {LY} Melatonin {} {} {} {LY} Melatonin {} {} {} {} {LY} Melatonin {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Melatonin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Melatonin
MDL Number	MFCD00005655
EC Number	200-797-7
Beilstein Registry Number	205542
PubChem Substance ID	896
Reaxys-RN	205542
Merck Number	5816
Chemical Name Translation	褪黑素
Wiswesser Line Notation	T56 BMJ D2MV1 GO1
LabNetwork Molecule ID	LN00194701
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)
Canonical SMILES	CC(NCCC1=CNC2=C1C=C(OC)C=C2)=O

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分类

{SNA} Analytical Standards, Pharmacopeia & Metrological Institutes Standards, USP Standards, USP Standards L - M, 分析/色谱
{SNA} Alkaloid, Application Index, Cell Signaling Enzymes, Cofactor, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Estrogen Response Modifiers, GPCR Modulators, GPCR Proteins, Modulators and Antibodies, Gene Regulation, L to O, Meatonin - Receptor Agonists, Melatonins, Membrane Protein Biology Tools, NOS - Nitric Oxide Inhibitors, Neurobiology, Neuroscience, Nitric Oxide Metabolism, Nitric Oxide Synthase, Pharmacologicals,
{SNA} Alkaloid,

产品应用

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安全信息

Signal word Warning

GHS Symbol

WGK Germany2

Safety Statements

Risk Statements

R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性

Precautionary statements

Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

RTECSAC5955000

Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 4200 mg/kg/20W-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Blood - leukemia
   Blood - lymphoma, including Hodgkin's disease
REFERENCE :
   GETRE8 Gematologiya i Transfuziologiya.  Hematology and Transfusion Science.
    (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.28-    1983-
   Volume(issue)/page/year: 28(2),47,1983

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 180 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems
   Laboratory, NIOSH Exchange Chemicals.  (Aberdeen Proving Ground, MD 21010)
   Volume(issue)/page/year: NX#02739

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1375 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   PCJOAU Pharmaceutical Chemistry Journal (English Translation).  Translation
   of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013)  No.1-
   1967-  Volume(issue)/page/year: 17,559,1983

TYPE OF TEST            : Mutation test systems - not otherwise specified
ROUTE OF EXPOSURE       : Subcutaneous
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 7 mg/kg/8W (Intermittent)
REFERENCE :
   CYTBAI Cytobios. (Faculty Press, 88 Regent St., Cambridge, UK)  V.1- 1969- 
   Volume(issue)/page/year: 65,115,1991

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 200 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 351,187,1996

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 80 ug/kg
SEX/DURATION            : male 20 day(s) pre-mating
TO

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - hamster
DOSE                    : 12 mg/kg
SEX/DURATION            : male 60 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
   Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland,
   accessory glands
   Reproductive - Paternal Effects - other effects on male
REFERENCE :
   HRMRA3 Hormone Research.  (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY
   10003)  V.4-    1978-  Volume(issue)/page/year: 15,99,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Mammal - domestic
DOSE                    : 1700 ug/kg
SEX/DURATION            : female 51 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Maternal Effects - menstrual cycle changes or disorders
REFERENCE :
   JANSAG Journal of Animal Science.  (American Soc. of Animal Science, 309 W.
   Clark St., Champaign, IL 61820)  V.1-    1942-  Volume(issue)/page/year:
   66,459,1988

{haz

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Ocular
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 375 ug/kg
SEX/DURATION            : female 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - other measures of fertility
REFERENCE :
   NUNDAJ Neuroendocrinology.  (S. Karger AG, Postfach CH-4009 Basel,
   Switzerland)  V.1-    1965/66-  Volume(issue)/page/year: 12,354,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE

{ha

Hazard statements

其他信息

{Chemicalbo
用途一:用于医药保健品，能增强人体的免疫机能，且是一种天然的“安眠药”
TCI Shanghai:退黑素 Melatonine,>;98.0%(LC)(N)(73-31-4)
图谱信息:松果体素(73-31-4)核磁图( 13 CNMR) 松果体素(73-31-4)核磁图( 1 HNMR) 松果体素(73-31-4)红外图谱(IR1) 松果体素(73-31-4)红外图谱(IR2) 松果体素(73-31-4)质谱(MS)
MSDS 信息:Melatonine(73-31-4).msds
松果体激素的合成与释放:松果体细胞从血循环中摄取色氨酸在羟化酶催化下变为5-羟色氨酸，后者
Acros Organics:褪黑素(即N-乙酰-5-甲氧基色胺) Melatonine, 99%(73-31-4)
松果体细胞分泌的一种激素:松果体素又称为褪黑素，是由松果体细胞分泌的一种激素，其化学结构为5-甲氧基-N-乙醯色胺，其生理作用为抑制性腺、甲状腺、肾上腺、甲状旁腺和垂体功能，抑制儿童性早熟，降低垂体促黑素分泌;并具有中枢神经系统作用，可提高惊厥阈值、引起嗜睡等。当切除松果体后实验动物示前述各腺体增生肥大，重量增加，尤其是未成熟大白鼠的性腺及性器官早熟，垂体分泌LH及FSH增加，甲状腺及肾上腺皮质激素分泌增多。松果体素更有降低垂体MSH而使皮肤变白的作用。此素作用于中枢神经，在人类脑电图上示慢节律，增高惊厥阈值，嗜睡，但不影响其行为和性格，对有颞叶癫痫者及巴金森病者可减轻其运动神经失常的脑电图变化。
松果体的生理作用:①对脑的作用：脑摄取的褪黑素浓集于中脑和丘脑下部，它增强脑吡哆醛激酶的活性，从而促进谷氨酸脱羧形成γ-氨基丁酸，5-羟色胺酸脱羧形成5-羟色胺，这两种抑制性神经递质含量的增加，对中枢起调整和镇静作用。 ②对下丘脑和垂体的作用：松果体产生的多肽类物质，除AVT外，尚有促甲状腺激素释放激素(TRH)和黄体生成激素释放激素(LRH)，与下丘脑产生的相同。注射褪黑素后可使促性腺激素(GnH) (FSH、LH)与黑素细胞刺激素(MSH)降低，而生长激素(GH)升高。切除松果体后引起垂体肥大，垂体GnH (FSH、LH)、ACTH分泌增加，而泌乳素(PRL)与抗利尿激素(ADH)降低。 ③与性腺的关系：松果体素对生殖系统具有抑制作用，临床上松果体主细胞瘤可导致青春期延迟，而松果体畸胎瘤时，由于主细胞被排挤，可并发性早熟。环境光照与交感神经可通过控制松果体褪黑素的合成与释放而影响生殖系统功能。 ④与甲状腺关系：给予褪黑素，则甲状腺激素分泌减少，可能是通过抑制下丘脑TRH释放以及垂体促甲状腺激素(TSH)分泌，从而抑制甲状腺功能。 ⑤与肾上腺皮质的关系：褪黑素对肾上腺皮质具有较强的抑制作用，给健康人注射松果体提取物，其醛固酮分泌减少，17酮类固醇排出量下降。 ⑥与胰岛的关系：松果体素可导致血糖降低，糖耐量增加。综上所述，松果体能协助垂体共同调节内分泌功能，对于维持机体内环境的相对恒定，控制某些内分泌功能，特别对性腺有重要作用。
Sigma Aldrich:73-31-4(sigmaaldrich)
松果体:松果体形似松果，约长7mm、宽5mm、厚4mm，重量140～200mg，位于中脑上丘之上，其后有大脑大静脉，胼胝体后部覆盖其上。发源于胚胎期第三脑室顶部的室管膜，由此向上突出而形成。其大部为软脑膜所包裹，软膜的结缔组织向内伸入把松果体分隔成不规则的小叶。交感神经颈上神经节节后纤维伴随血管进入松果体。松果体是由大量的松果体细胞和少量的胶质细胞组成，松果体细胞呈多边形、长柱形或椭圆形，胞突长短不一，胞浆为嗜碱性，常含有类脂滴，核大，呈不规则凹陷或分叶状，有核仁。电镜下胞质中可见高尔基复合体发达，粗面内质网丰富，富于游离核蛋白体、溶酶体以及大量微管和分泌颗粒小泡，后者还出现于胞突内，小泡内含去甲肾上腺素、多巴胺、5-羟色胺和松果体素，又称褪黑素等。胶质细胞也具有突起、核椭圆形，核和胞质染色均较深，电镜下胞质内也有粗面内质网，游离核蛋白体，以富于微丝而能和松果体细胞相区别。松果体内还见有多量的凝固体，内含羟磷灰石和碳酸钙磷灰石，往往结成桑椹状小块，称脑砂，其大小和数量随年龄而增加。
F:8-10-23
检测方法:HPLC,NMR