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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

Quality Level

200

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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
Exogenous melatonin inhibits neutrophil migration through suppression of ERK activation
Ren DL, et al.
The Journal of Endocrinology, 227(1), 49-60 (2015)
M L Dubocovich
The Journal of pharmacology and experimental therapeutics, 246(3), 902-910 (1988-09-01)
The pharmacological potencies of 2-substituted N-acetyltryptamines were determined on the presynaptic melatonin receptor site of rabbit retina labeled in vitro with [3H]dopamine. Calcium-dependent release of [3H]dopamine was elicited by electrical stimulation at 3 Hz for 2 min (20 mA, 2
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