6-Hydroxymelatonin

Names

[ CAS No. ]:
2208-41-5

[ Name ]:
6-Hydroxymelatonin

[Synonym ]:
6-HydroxyMelatonin
6-Hydroxy Melatonin
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

Biological Activity

[Description]:

6-Hydroxymelatonin is a primary metabolic of Melatonin, which is metabolized by cytochrome P450 (CYP) 1A2.

[Related Catalog]:

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

Natural Products >> Others

[Target]

Human Endogenous Metabolite

[References]

[1]. Härtter S, et al. Orally given melatonin may serve as a probe drug for cytochrome P450 1A2 activity in vivo: a pilot study. Clin Pharmacol Ther. 2001 Jul;70(1):10-6.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.266g/cm3

[ Boiling Point ]:
564.7ºC at 760mmHg

[ Melting Point ]:
172-175ºC

[ Molecular Formula ]:
C₁₃H₁₆N₂O₃

[ Molecular Weight ]:
248.27800

[ Flash Point ]:
295.3ºC

[ Exact Mass ]:
248.11600

[ PSA ]:
74.35000

[ LogP ]:
1.95160

[ Vapour Pressure ]:
2.35E-13mmHg at 25°C

[ Index of Refraction ]:
1.627

[ Storage condition ]:
Refrigerator

[ Water Solubility ]:
alcohol: soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC3607000

CHEMICAL NAME :: Acetamide, N-(2-(6-hydroxy-5-methoxyindol-3-yl)ethyl)-

CAS REGISTRY NUMBER :: 2208-41-5

BEILSTEIN REFERENCE NO. :: 0483231

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C13-H16-N2-O3

MOLECULAR WEIGHT :: 248.31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 8 mg/kg

SEX/DURATION :: male 20 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: BIREBV Biology of Reproduction. (Soc. for the Study of Reproduction, 309 W. Clark St., Champaign, IL 61820) V.1- 1969- Volume(issue)/page/year: 33,618,1985

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H351

[ Precautionary Statements ]:
P281

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
22-40

[ Safety Phrases ]:
36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AC3607000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail 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%

Articles

Melatonin and its metabolites accumulate in the human epidermis in vivo and inhibit proliferation and tyrosinase activity in epidermal melanocytes in vitro.

Mol. Cell. Endocrinol. 404 , 1-8, (2015)

Melatonin and its metabolites including 6-hydroxymelatonin (6(OH)M), N(1)-acetyl-N(2)-formyl-5-methoxykynuramine (AFMK) and 5-methoxytryptamine (5MT) are endogenously produced in human epidermis. This...

Predominance of 2-hydroxymelatonin over melatonin in plants.

J. Pineal Res. 59 , 448-54, (2015)

The cloning of the gene encoding melatonin 2-hydroxylase (M2H), which is responsible for the synthesis of 2-hydroxymelatonin, has expanded the study of melatonin metabolism in plants. Kinetic analysis...

Molecular cloning of melatonin 2-hydroxylase responsible for 2-hydroxymelatonin production in rice (Oryza sativa).

J. Pineal Res. 58(3) , 343-51, (2015)

Although melatonin biosynthetic genes from plants have been cloned, the melatonin catabolism mechanisms remain unclear. To clone the genes responsible for melatonin metabolism, we ectopically expresse...