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2208-40-4

2208-40-4 | N-[2-[5-Methoxy-6-(sulfooxy)-1H-indol-3-yl]ethyl]acetamide

CAS No: 2208-40-4 Catalog No: AG003AM3 MDL No:

Product Description

Catalog Number:
AG003AM3
Chemical Name:
N-[2-[5-Methoxy-6-(sulfooxy)-1H-indol-3-yl]ethyl]acetamide
CAS Number:
2208-40-4
Molecular Formula:
C13H16N2O6S
Molecular Weight:
328.3409
IUPAC Name:
[3-(2-acetamidoethyl)-5-methoxy-1H-indol-6-yl] hydrogen sulfate
InChI:
InChI=1S/C13H16N2O6S/c1-8(16)14-4-3-9-7-15-11-6-13(21-22(17,18)19)12(20-2)5-10(9)11/h5-7,15H,3-4H2,1-2H3,(H,14,16)(H,17,18,19)
InChI Key:
QQEILXDLZRLTME-UHFFFAOYSA-N
SMILES:
COc1cc2c(CCNC(=O)C)c[nH]c2cc1OS(=O)(=O)O

Properties

Complexity:
491  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
328.073g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
328.339g/mol
Monoisotopic Mass:
328.073g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
126A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.6  

Literature

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Low urinary 6-sulfatoxymelatonin levels in patients with severe congestive heart failure. Endocrine 20031201
Urinary 6-sulfatoxymelatonin excretion in hyperandrogenic women with polycystic ovary syndrome: the effect of ethinyl estradiol-cyproterone acetate treatment. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20031201
Urinary 6-hydroxy-melatonin-sulfate excretion and circadian rhythm in patients with restless legs syndrome. Journal of pineal research 20031101
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Reproducibility over 5 years of measurements of 6-sulphatoxymelatonin in urine samples from postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20030801
Non-24-hour sleep-wake syndrome following a car accident. Neurology 20030610
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Effect of stress on pregnancy outcome among women undergoing assisted reproduction procedures. Southern medical journal 20030601
Interruption of the rat circadian clock by short light-dark cycles. American journal of physiology. Regulatory, integrative and comparative physiology 20030501
Luteinizing hormone following light exposure in healthy young men. Neuroscience letters 20030424
Effects of mobile phone radiation on UV-induced skin tumourigenesis in ornithine decarboxylase transgenic and non-transgenic mice. International journal of radiation biology 20030401
[Video screen exposure and 6-sulfatoxymelatonin urinary excretion in women]. Pathologie-biologie 20030401
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Hormonal changes during 17 days of head-down bed-rest. Life sciences 20030117
Melatonin production during childhood and adolescence: a longitudinal study on the excretion of urinary 6-hydroxymelatonin sulfate. Journal of pineal research 20030101
Impaired nocturnal melatonin secretion in non-dipper hypertensive patients. Blood pressure 20030101
The relation between the clinical subtypes of delirium and the urinary level of 6-SMT. The Journal of neuropsychiatry and clinical neurosciences 20030101
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Massage therapy by mothers enhances the adjustment of circadian rhythms to the nocturnal period in full-term infants. Journal of developmental and behavioral pediatrics : JDBP 20021201
Melatonin metabolite excretion among cellular telephone users. International journal of radiation biology 20021101
Human circadian phase in 12:12 h, 200: <8 lux and 1000: <8 lux light-dark cycles, without scheduled sleep or activity. Neuroscience letters 20020823
Cyproterone acetate-ethinyl estradiol treatment alters urinary 6-sulfatoxymelatonin excretion in hyperandrogenic women. Neuro endocrinology letters 20020801
Interleukin-1beta-induced increases of plasma catecholamine levels in rats: enhancement by superior cervical ganglionectomy. Pharmacology 20020701
No association of 6-sulfatoxymelatonin with in-bed 60-Hz magnetic field exposure or illumination level among older adults. Environmental research 20020701
Adaptation of the circadian rhythm of 6-sulphatoxymelatonin to a shift schedule of seven nights followed by seven days in offshore oil installation workers. Neuroscience letters 20020607
[Melatonin/circadian rhythm. Is there a feedback between epiphysis and hypophysis?]. Minerva endocrinologica 20020601
Melatonin production in infants. Pediatric neurology 20020501
Depression and endogenous melatonin in postmenopausal women. Journal of affective disorders 20020501
Sulphatoxymelatonin excretion during opiate withdrawal: a preliminary study. Progress in neuro-psychopharmacology & biological psychiatry 20020501
The effects of coffee consumption on sleep and melatonin secretion. Sleep medicine 20020501
One week of exposure to 50 Hz, vertical magnetic field does not reduce urinary 6-sulphatoxymelatonin excretion of male wistar rats. Bioelectromagnetics 20020401
Melatonin rhythms in stroke patients. Neuroscience letters 20020215
Melatonin in mice: rhythms, response to light, adrenergic stimulation, and metabolism. American journal of physiology. Regulatory, integrative and comparative physiology 20020201
Bright-light mask treatment of delayed sleep phase syndrome. Journal of biological rhythms 20020201
[Urinary excretion of 6-sulphatoxymelatonin in normal subjects: statistical approach to the influence of age and sex]. Annales d'endocrinologie 20020201
Circadian phase-delaying effects of bright light alone and combined with exercise in humans. American journal of physiology. Regulatory, integrative and comparative physiology 20020101
A multifactorial approach employing melatonin to accelerate resynchronization of sleep-wake cycle after a 12 time-zone westerly transmeridian flight in elite soccer athletes. Journal of pineal research 20020101
The influence of anaesthesia and surgery on the circadian rhythm of melatonin. Acta anaesthesiologica Scandinavica 20020101
Marker rhythms of circadian system function: a study of patients with metastatic colorectal cancer and good performance status. Chronobiology international 20020101
Late nocturnal sleep onset impairs a melatonin shower in young children. Neuro endocrinology letters 20020101
[Evaluation of the effect of magnetic fields on the secretion of melatonin in humans and rats. Circadian study]. Bulletin de l'Academie nationale de medecine 20020101
Physiological effects of shift work on hospital nurses. Journal of human ergology 20011201
Contribution of CYP1A2 in the hepatic metabolism of melatonin: studies with isolated microsomal preparations and liver slices. Journal of pineal research 20011101
Residential magnetic fields, light-at-night, and nocturnal urinary 6-sulfatoxymelatonin concentration in women. American journal of epidemiology 20011001
Effects of electric and magnetic fields from high-power lines on female urinary excretion of 6-sulfatoxymelatonin. American journal of epidemiology 20011001
Clearance of melatonin and 6-sulfatoxymelatonin by hemodialysis in patients with end-stage renal disease. Journal of pineal research 20011001
Daytime 50 Hz magnetic field exposure and plasma melatonin and urinary 6-sulfatoxymelatonin concentration profiles in humans. Journal of pineal research 20011001
Circadian abnormalities in older adults. Journal of pineal research 20011001
Increased urinary 6-sulfatoxymelatonin excretion in women with non-classical steroid 21-hydroxylase deficiency. Neuro endocrinology letters 20011001
Profile of 24-h light exposure and circadian phase of melatonin secretion in night workers. Journal of biological rhythms 20011001
Increased 6-sulfatoxymelatonin excretion in women with polycystic ovary syndrome. Fertility and sterility 20010901
All-night exposure to EMF does not alter urinary melatonin, 6-OHMS or immune measures in older men and women. Journal of pineal research 20010901
Circadian urinary 6-sulphatoxymelatonin, cortisol excretion and locomotor activity in airline pilots during transmeridian flights. Journal of pineal research 20010801
Seasonal rhythms of 6-sulphatoxymelatonin (aMT6s) excretion in female rats are abolished by growth of malignant tumors. Journal of pineal research 20010801
Melatonin and 6-OHMS in high-intensity magnetic fields. Journal of pineal research 20010801
Stereoselective effects of (R)- and (S)-carvedilol in humans. Chirality 20010701
Resynchronization of hormonal rhythms after an eastbound flight in humans: effects of slow-release caffeine and melatonin. European journal of applied physiology 20010701
Noradrenergic function and clinical outcome in antidepressant pharmacotherapy. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20010601
Phase response relationships between light pulses and the melatonin rhythm in rats. Journal of biological rhythms 20010601
Actigraphic sleep-wake patterns and urinary 6-sulfatoxymelatonin excretion in patients with Alzheimer's disease. Chronobiology international 20010501
The impact of fetal size and length of gestation on 6-sulphatoxymelatonin excretion in adult life. Journal of pineal research 20010401
Plasma melatonin concentration before and during testosterone replacement in Klinefelter's syndrome: relation to hepatic indolamine metabolism and sympathoadrenal activity. The Journal of clinical endocrinology and metabolism 20010201
A single nocturnal exposure to 2-7 millitesla static magnetic fields does not inhibit the excretion of 6-sulfatoxymelatonin in healthy young men. Bioelectromagnetics 20010101
Melatonin production in healthy infants: evidence for seasonal variations. Pediatric research 20010101
Lack of changes in serum prolactin, FSH, TSH, and estradiol after melatonin treatment in doses that improve sleep and reduce benzodiazepine consumption in sleep-disturbed, middle-aged, and elderly patients. Journal of pineal research 20010101
Interaction between the adrenal and the pineal gland in chronic experimental inflammation induced by BCG in mice. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20010101
Is melatonin circadian rhythm a physiological feature associated with healthy longevity? A study of long-living subjects and their progeny. Chronobiology international 20010101
Plasma melatonin levels in relation to the light-dark cycle and parental background in domestic pigs. Acta veterinaria Scandinavica 20010101
Artificially accelerated aging by shortened photoperiod alters early gene expression (Fos) in the suprachiasmatic nucleus and sulfatoxymelatonin excretion in a small primate, Microcebus murinus. Neuroscience 20010101

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