5-methoxytryptophol

[Description]:

5-Methoxytryptophol is a natural indole present in the pineal gland.

[Related Catalog]:

Natural Products >> Others

Research Areas >> Others

[Target]

Human Endogenous Metabolite

[References]

[1]. Satué M, et al. A new role for 5-methoxytryptophol on bone cells function in vitro. J Cell Biochem. 2015 Apr;116(4):551-8.

[2]. Raynaud F, et al. Plasma concentrations of 5-methoxytryptamine, 5-methoxytryptophol and melatonin after 5-methoxytryptamine administration of golden hamsters: physiological implications. J Neural Transm Gen Sect. 1991;84(1-2):33-43.

[Related Small Molecules]

[ Density]:
1.224 g/cm3

[ Boiling Point ]:
393.9ºC at 760 mmHg

[ Molecular Formula ]:
C₁₁H₁₃NO₂

[ Molecular Weight ]:
191.22600

[ Flash Point ]:
192ºC

[ Exact Mass ]:
191.09500

[ PSA ]:
45.25000

[ LogP ]:
1.71130

[ Index of Refraction ]:
1.64

[ Storage condition ]:
2-8°C

Click to get detail MSDS

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL8513000

CHEMICAL NAME :: Indole-3-ethanol, 5-methoxy-

CAS REGISTRY NUMBER :: 712-09-4

BEILSTEIN REFERENCE NO. :: 0145680

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C11-H13-N-O2

MOLECULAR WEIGHT :: 191.25

WISWESSER LINE NOTATION :: T56 BMJ D2Q GO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 9333 ug/kg

SEX/DURATION :: female 28 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - menstrual cycle changes or disorders

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 145,63,1964

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 25200 ug/kg

SEX/DURATION :: male 21 day(s) pre-mating

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

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 30,305,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 240 mg/kg

SEX/DURATION :: female 1-2 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: JNTMAH Journal of Neural Transmission. (Springer-Verlag, Postfach 367, A-1011 Vienna, Austria) V.33-77, 1972-89. Volume(issue)/page/year: 96,19,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 750 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: ENDOAO Endocrinology (Baltimore). (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21203) V.1- 1917- Volume(issue)/page/year: 83,599,1968

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NL8513000

[ HS Code ]:
2933990090

Click to get detail synthetic route

Precursor

DownStream

[ 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%

Serine residues 110 and 114 are required for agonist binding but not antagonist binding to the melatonin MT(1) receptor.

Biochem. Biophys. Res. Commun. 282(5) , 1229-36, (2001)

Site-directed mutation of serine 110 (Ser(3.35)) and serine 114 (Ser(3.39)) in the human melatonin MT(1) receptor to alanine residues reduced ligand binding affinities of seven known melatonin recepto...

Effects of cycloheximide and aminophylline on 5-methoxytryptophol and melatonin contents in the chick pineal gland.

Gen. Comp. Endocrinol. 120(2) , 212-9, (2000)

The chick pineal gland rhythmically synthesizes two 5-methoxyindoles, melatonin and 5-methoxytryptophol. These rhythms are circadian in nature and have opposite phases. The aim of this study was to de...

5-methoxytryptophol preserves hepatic microsomal membrane fluidity during oxidative stress.

J. Cell. Biochem. 76(4) , 651-7, (2000)

Lipid peroxidation is a degenerative chain reaction in biological membranes that may be initiated by exposure to free radicals. This process is associated with changes in the membrane fluidity and los...

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Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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Precursor & DownStream

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