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Merck

31742

Levamisol hydrochloride

VETRANAL®, analytical standard

Synonym(s):

(−)-Tetramisole hydrochloride, (S)-(−)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride, L(−)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride, Levamisole hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C11H12N2S · HCl
CAS Number:
16595-80-5
Molecular Weight:
240.75
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329753914
EC Number:
240-654-6
Beilstein/REAXYS Number:
4358988
MDL number:
MFCD00012675

Product Name

Levamisol hydrochloride, VETRANAL®, analytical standard

InChI

1S/C11H12N2S.ClH/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10;/h1-5,10H,6-8H2;1H/t10-;/m1./s1

InChI key

LAZPBGZRMVRFKY-HNCPQSOCSA-N

SMILES string

Cl.C1CN2C[C@@H](N=C2S1)c3ccccc3

grade

analytical standard

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

228-230 °C

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

Quality Level

100

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Application

Levamisol hydrochloride may have been used as antibiotic standard in ultra-high-pressure liquid chromatography–tandem mass spectrometry for determination of veterinary drug residues from milk samples.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Shows both immunostimulant and immunosuppressant effects, depending on several controllable factors. Very effective in treatment of ascariasis (hookworm infestation). Useful in chemotherapy of colorectal cancers, possibly due to its stimulation of IL-1 production and direct activation of macrophages.

General description

Levamisol hydrochloride is an anthelmintic drug which possesses immunomodulatory and anticancer properties. It is a white crystalline compound which is stable in acid aqueous media, whereas it hydrolyzes in alkaline/neutral solutions.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2387
BCCH9592
BCCF7363
BCCB8126
BCBZ3833

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Potentiometric sensing of levamisole hydrochloride based on molecularly imprinted polymer.
Sadeghi, Susan, Fatemeh Fathi, and Javad Abbasifar.
Sensors and Actuators B, Chemical, 122.1, 158-164 (2007)
Jennifer E Hewitt et al.
Disease models & mechanisms, 11(12) (2018-11-07)
Muscle strength is a key clinical parameter used to monitor the progression of human muscular dystrophies, including Duchenne and Becker muscular dystrophies. Although Caenorhabditis elegans is an established genetic model for studying the mechanisms and treatments of muscular dystrophies, analogous
A molecular imprinted membrane for molecular discrimination of tetracycline hydrochloride.
Trotta, F., et al.
Journal of Membrane Science, 254.1, 13-19 (2005)
Lei Chang et al.
Bioorganic & medicinal chemistry letters, 21(8), 2297-2301 (2011-03-23)
Pathological calcifications induced by deposition of basic phosphate crystals or hydroxyapatite (HA) on soft tissues are a large family of diseases comprising of ankylosing spondylitis (AS), end-stage osteoarthritis (OA) and vascular calcification. High activity of tissue non-specific alkaline phosphatase (TNAP)
Lina Li et al.
Bioorganic & medicinal chemistry, 17(20), 7290-7300 (2009-09-29)
Presence of basic calcium phosphate in knee joints of osteoarthritis patients could be prevented by inhibiting tissue non-specific alkaline phosphatase (TNAP) activity. Levamisole or the L stereoisomer of tetramisole (a known TNAP inhibitor) has been used as a treatment for
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