Melatonine

Modify Date: 2024-01-02 12:08:13

Melatonine Structure
Melatonine structure
 Common Name Melatonine
CAS Number 73-31-4 Molecular Weight 232.278
Density 1.2±0.1 g/cm3 Boiling Point 459.8±55.0 °C at 760 mmHg
Molecular Formula C13H16N2O2 Melting Point 116.5-118 °C(lit.)
MSDS Chinese USA Flash Point 231.9±31.5 °C
Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08		 Signal Word Danger

 Use of Melatonine


Melatonin is a hormone made by the pineal gland that can activates melatonin receptor. Melatonin plays a role in sleep and possesses important antioxidative and anti-inflammatory properties.

 Names

Name melatonin
Synonym More Synonyms

 Melatonine Biological Activity

Description Melatonin is a hormone made by the pineal gland that can activates melatonin receptor. Melatonin plays a role in sleep and possesses important antioxidative and anti-inflammatory properties.
Related Catalog
Target

Human Endogenous Metabolite

In Vivo Melatonin increases the levels of activated PTEN, RSK-1, mTOR and AMPKα kinases, mildly inhibits ERK-1/2 phosphorylation and Bad phosphorylation, significantly inhibits phosphorylations of S6 Ribosomal Protein, 4E-BP1, GSK-3α and GSK-3β, and slightly increases PRAS40 phosphorylation in animals[1]. Melatonin ameliorates the neurotoxiciy and astrocyte activation induced by Aβ1-42 in the cerebral cortex. Melatonin also blocks the reduction in Reelin and Dab1 expression induced by Aβ1-42[2]. Melatonin treatment and lack of NLRP3-/- share similar inhibition of NF-κB and NLRP3 signaling pathway in mice. Melatonin treatment and lack of NLRP3-/- share some patterns of clock genes expression, and improve cardiomyocytes morphology in mice[3].
Animal Admin A total of two sets of adult male C57BL/6j mice weighing 21-26 g are randomly assigned to one of four groups and treated with intraperitoneal (i.p.) delivery of (i) vehicle (50 μL isotonic saline/5% ethanol), (ii) melatonin (4 mg/kg, dissolved in 0.9% isotonic saline/5% ethanol), (iii) Wortmannin, and (iv) melatonin/Wortmannin immediately after reperfusion. In the first set, mice are exposed to 30 min of focal cerebral ischemia (FCI) and 72 h reperfusion for the evaluation of disseminate ischemic injury in the striatum, and signaling pathway analysis (n=7 per group). The second group of mice is exposed to 90 min of FCI and 24 h reperfusion for the analysis of infarct development, brain swelling and IgG extravasation (n=7 per group).
References

[1]. Kilic U, et al. Particular phosphorylation of PI3K/Akt on Thr308 via PDK-1 and PTEN mediates melatonin's neuroprotective activity after focal cerebral ischemia in mice. Redox Biol. 2017 Apr 5;12:657-665

[2]. Hu C, et al. Neuroprotective effect of melatonin on soluble Aβ1-42-induced cortical neurodegeneration via Reelin-Dab1 signaling pathway. Neurol Res. 2017 Apr 7:1-1

[3]. Rahim I, et al. Melatonin administration to wild-type mice and non-treated NLRP3 mutant mice share similar inhibition of the inflammatory response during sepsis. J Pineal Res. 2017 Mar 31

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 459.8±55.0 °C at 760 mmHg
Melting Point 116.5-118 °C(lit.)
Molecular Formula C13H16N2O2
Molecular Weight 232.278
Flash Point 231.9±31.5 °C
Exact Mass 232.121185
PSA 54.12000
LogP 1.94
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.580
Storage condition -15°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AC5955000
CHEMICAL NAME :
Acetamide, N-(2-(5-methoxyindol-3-yl)ethyl)-
CAS REGISTRY NUMBER :
73-31-4
BEILSTEIN REFERENCE NO. :
0205542
LAST UPDATED :
199806
DATA ITEMS CITED :
39
MOLECULAR FORMULA :
C13-H16-N2-O2
MOLECULAR WEIGHT :
232.31
WISWESSER LINE NOTATION :
T56 BMJ D2MV1 GO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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
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
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15 mg/kg/2W-I
TOXIC EFFECTS :
Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count
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
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
27 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2800 ug/kg
SEX/DURATION :
female 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
140 ug/kg
SEX/DURATION :
female 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
7500 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
900 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1400 ug/kg
SEX/DURATION :
female 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
140 ug/kg
SEX/DURATION :
female 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
80 ug/kg
SEX/DURATION :
male 20 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
500 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
500 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Ocular
DOSE :
375 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Ocular
DOSE :
50 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
36 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
4 mg/kg
SEX/DURATION :
female 19 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
560 mg/kg
SEX/DURATION :
female 70 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Specific Developmental Abnormalities - endocrine system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
14 mg/kg
SEX/DURATION :
male 70 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
70 mg/kg
SEX/DURATION :
male 70 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
5600 ug/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
7500 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
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
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1260 ug/kg
SEX/DURATION :
female 9 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
9800 ug/kg
SEX/DURATION :
female 49 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
7 mg/kg
SEX/DURATION :
male 35 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
21 mg/kg
SEX/DURATION :
male 15 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
14 mg/kg
SEX/DURATION :
female 10 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - other effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
12480 ug/kg
SEX/DURATION :
male 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
4032 ug/kg
SEX/DURATION :
male 42 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1700 ug/kg
SEX/DURATION :
female 51 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1429 ug/kg
SEX/DURATION :
female 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Maternal Effects - other effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1200 ug/kg
SEX/DURATION :
female 40 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
16 mg/kg
SEX/DURATION :
female 17 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - endocrine system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravaginal
DOSE :
4600 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects

MUTATION DATA

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

 Safety Information

Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger
Hazard Statements H225-H301 + H311 + H331-H370
Precautionary Statements P210-P260-P280-P301 + P310-P311
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes T
Risk Phrases R60
Safety Phrases S24/25
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS AC5955000
HS Code 2932999099

 Synthetic Route

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

Melatonin
EINECS 200-797-7
N-(2-(5-methoxyindol-3-yl)ethyl)-Acetamide
Melovine
Melatonine
primex
Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-
MLT
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-Acetamide
N-[2-(5-methoxyindol-3-yl)ethyl]-Acetamide
N-acetyl-5-methoxytryptamine
Circadin
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide
MFCD00005655
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