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L2407

Sigma-Aldrich

Luzindole

≥90%

Synonym(s):

N-Acetyl-2-benzyltryptamine, N-[2-[2-(Phenylmethyl)-1H-indol-3-yl]ethyl]acetamide

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About This Item

Empirical Formula (Hill Notation):
C19H20N2O
CAS Number:
117946-91-5
Molecular Weight:
292.37
MDL number:
MFCD00672498
UNSPSC Code:
12352200
PubChem Substance ID:
24896315
NACRES:
NA.77

Assay

≥90%

solubility

DMSO: 5 mg/mL

storage temp.

−20°C

SMILES string

CC(=O)NCCc1c(Cc2ccccc2)[nH]c3ccccc13

InChI

1S/C19H20N2O/c1-14(22)20-12-11-17-16-9-5-6-10-18(16)21-19(17)13-15-7-3-2-4-8-15/h2-10,21H,11-13H2,1H3,(H,20,22)

InChI key

WVVXBPKOIZGVNS-UHFFFAOYSA-N

Gene Information

human ... MTNR1A(4543) , MTNR1B(4544)

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Application

Luzindole has been used as a MT1/MT2 receptor antagonist to detect the role of the melatonin receptor in neutrophil migration

Biochem/physiol Actions

Luzindole is a melatonin (mel) receptor antagonist. It has higher affinity towards the Mel 1b receptor than the Mel 1a receptor subtype.

Features and Benefits

This compound is featured on the Melatonin Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alicia González et al.
Journal of pineal research, 52(1), 12-20 (2011-07-02)
Melatonin inhibits the genesis and growth of breast cancer by interfering at different levels in the estrogen-signaling pathways. Melatonin inhibits aromatase activity and expression in human breast cancer cells, thus behaving as a selective estrogen enzyme modulator. As the adipose
Exogenous melatonin inhibits neutrophil migration through suppression of ERK activation
Ren DL, et al.
The Journal of Endocrinology, 227(1), 49-60 (2015)
Sameer Gupta et al.
The Journal of steroid biochemistry and molecular biology, 134, 23-36 (2012-10-13)
Immunoenhancing attributes of melatonin (Mel) on the immunocompromised state induced by glucocorticoid is well known, but the involvement of their receptors in the modulation of immunity has never been studied in any rodent. The present study explores the role of
Melatonin enhancement of splenocyte proliferation is attenuated by luzindole, a melatonin receptor antagonist
Drazen DL, et al.
American Journal of Physiology. Regulatory, Integrative and Comparative Physiology, 280(5), R1476-R1482 (2001)
Naree Song et al.
Journal of pineal research, 53(4), 335-343 (2012-04-28)
Melatonin is an indolamine that is synthesized in the pineal gland and shows a wide range of physiological functions. Although the anti-aging properties of melatonin have been reported in a senescence-accelerated mouse model, whether melatonin modulates cellular senescence has not
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