CAS 73-31-4|Melatonine

Introduction：Basic information about CAS 73-31-4|Melatonine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Melatonine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles363
8. Synonyms

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	ChineseUSA	Flash Point	231.9±31.5 °C
Symbol	GHS02, GHS06, GHS08	Signal Word	Danger

Names

Name	melatonin
Synonym	More Synonyms

Melatonine BiologicalActivity

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	Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>GPCR/G Protein >>Melatonin ReceptorSignaling Pathways >>Neuronal Signaling >>Melatonin ReceptorSignaling Pathways >>Autophagy >>MitophagyResearch Areas >>Neurological DiseaseNatural Products >>Others
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
InChIKey	DRLFMBDRBRZALE-UHFFFAOYSA-N
SMILES	COc1ccc2[nH]cc(CCNC(C)=O)c2c1
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
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

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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