5-methoxytryptophol

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Names

[ CAS No. ]:
712-09-4

[ Name ]:
5-methoxytryptophol

[Synonym ]:
EINECS 211-919-3
MFCD00047196
2-(5-methoxy-1H-indol-3-yl)ethanol

Chemical & Physical Properties

[ 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

MSDS

Click to get detail MSDS

Toxicological Information

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

Safety Information

[ 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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • 2,3-DHF
  • 4-Anisylhydrazine hydrochloride
  • ethyl 2-(5-methoxy-1h-indol-3-yl)-2-oxoacetate
  • 1-(tert-Butyldimethylsilyl)-3-(2-hydroxyethyl)-5-methoxyindole
  • 5-Methoxyindole-3-acetic acid
  • 5-Methoxy-1H-indole-3-acetic acid methyl ester
  • p-anisylhydrazine
  • 5-methoxy-1H-indol-3-ylacetic acid ethyl ester
  • methyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate
  • 5-Methoxyindole

DownStream

  • 5-Methoxy-3-indoleaceate
  • 3-(2-bromoethyl)-5-methoxy-1-methylindole
  • Melatonine
  • 5-Methoxydimethyltryptamine

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

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...


More Articles

Related Compounds

  • n-boc-5-methoxytryptophol
  • 5-Methoxytryptophol-benzene-d4
  • 5-(2,4-difluorophenyl)-2-hydroxy-3-sulfooxybenzoic acid
  • 5-(3-formyl-4-hydroxyphenyl)benzene-1,3-dicarboxylic acid
  • (5-Bromo-1H-indol-3-yl)-acetic acid methyl ester
  • 5-(p-Toluenesulfonate)-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone
  • 3-Bromo-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid
  • 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)quinazoline-7-sulfonamide
  • 5-Cyclohexyl-2-methyl-2-penten-1-ol
  • (2E)-3-(1-benzothiophen-7-yl)prop-2-enoic acid
  • 2-(Benzo[b]thiophen-7-yl)pyrrolidine
  • 2-(Aminomethyl)-1-(1-methylcyclopentyl)butan-1-ol
  • 4-Isopropoxybenzo[b]thiophene-6-carboxylic acid
  • 4-Isopropoxy-2-naphthoic acid
  • 3-(5-Bromo-2-hydroxy-3-methoxyphenyl)prop-2-enoic acid
  • 2-Bromo-N-(cyclopropylmethyl)-5-methylbenzamide