A7342
N-Acetyltryptamine
powder
Synonym(s):
3-(2-N-Acetylaminoethyl)indole
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About This Item
Empirical Formula (Hill Notation):
C12H14N2O
CAS Number:
Molecular Weight:
202.25
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
InChI
1S/C12H14N2O/c1-9(15)13-7-6-10-8-14-12-5-3-2-4-11(10)12/h2-5,8,14H,6-7H2,1H3,(H,13,15)
SMILES string
CC(=O)NCCc1c[nH]c2ccccc12
InChI key
NVUGEQAEQJTCIX-UHFFFAOYSA-N
form
powder
solubility
alcohol: soluble
storage temp.
2-8°C
Gene Information
human ... MTNR1A(4543), MTNR1B(4544)
General description
N-Acetyltryptamine is a melatonin analog present in mammalian blood. It is derived from tryptophan.
Application
N-Acetyltryptamine has been used as an internal standard in liquid chromatography-tandem mass spectrometry (LC/MS/MS). It has also been used as an internal standard in melatonin concentration assay and tandem mass spectrometry for the quantification of plasma melatonin levels.
Biochem/physiol Actions
Mixed agonist-antagonist at melatonin receptors; antioxidant.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Rashidul Haque et al.
Molecular vision, 9, 52-59 (2003-03-12)
Arylalkylamine N-acetyltransferase (AANAT) is a key regulatory enzyme in the synthesis of melatonin, which displays daily fluctuations in chicken retinal photoreceptors in vivo. The purpose of the present study was to determine if cultures of embryonic neural retina cells express
M L Dubocovich
The Journal of pharmacology and experimental therapeutics, 234(2), 395-401 (1985-08-01)
Melatonin (5-methoxy-N-acetyltryptamine) at picomolar concentrations (IC50, 40 pM) inhibited the calcium-dependent release of [3H]dopamine elicited at 3 Hz (2 min, 20 mA, 2 msec) from rabbit retina through activation of a site possessing the pharmacological and functional characteristics of a
Amanda Lochner et al.
Journal of pineal research, 40(1), 56-63 (2005-11-30)
Melatonin, the chief secretory product of the pineal gland, has been shown to protect the heart against ischemia-reperfusion injury. This was attributed to its free radical scavenging and broad-spectrum antioxidant properties. The possibility that melatonin may act via its receptor
K B Thomas et al.
Analytical biochemistry, 184(2), 228-234 (1990-02-01)
A sensitive, rapid, and economical method has been developed for determination of serotonin N-acetyltransferase activity from a variety of enzyme sources. The assay is based upon separation and detection of N-acetyltryptamine formed from tryptamine and acetyl coenzyme A, by means
Igor Semak et al.
Archives of biochemistry and biophysics, 421(1), 61-66 (2003-12-18)
We have recently uncovered the full expression of novel cutaneous serotoninergic and melatoninergic systems in the human and hamster skin. In this work, we have characterized serotonin metabolism in the rat skin using liquid chromatography-mass spectrometry and found that serotonin
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