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L9756

(−)-Tetramisole hydrochloride

Name: (−)-Tetramisole hydrochloride
Brand: SIGMA

powder, ≥99% (GC)

Synonym(s):

(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

Beilstein:

4358988

EC Number:

240-654-6

MDL number:

MFCD00012675

UNSPSC Code:

12352202

PubChem Substance ID:

24278526

NACRES:

NA.77

product name

(−)-Tetramisole hydrochloride, ≥99% (GC)

biological source

synthetic (organic)

Quality Level

200

Assay

≥99% (GC)

form

powder

mp

228-230 °C

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

antibiotic activity spectrum

parasites

Mode of action

enzyme | inhibits

SMILES string

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

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

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Application

Suitable for inhibition of various mammalian alkaline phosphatase (i.e., liver, kidney, placenta, bone and tumor).
Intestinal alkaline phosphatases are only slightly inhibited.
Not for veterinary use.

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.

Other Notes

Levamisole hydrochloride is soluble in water at 50mg/mL yielding a clear, colorless solution. Solutions are stable at 2-8°C for ~1 month.

Pictograms

GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral

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)

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Quantification of Tyrosine Hydroxylase and ErbB4 in the Locus Coeruleus of Mood Disorder Patients Using a Multispectral Method to Prevent Interference with Immunocytochemical Signals by Neuromelanin.

Lei Guo et al.

Neuroscience bulletin, 35(2), 205-215 (2019-02-02)

The locus coeruleus (LC) has been studied in major depressive disorder (MDD) and bipolar disorder (BD). A major problem of immunocytochemical studies in the human LC is interference with the staining of the immunocytochemical end-product by the omnipresent natural brown

Entosis Controls a Developmental Cell Clearance in C. elegans.

Yongchan Lee et al.

Cell reports, 26(12), 3212-3220 (2019-03-21)

Metazoan cell death mechanisms are diverse and include numerous non-apoptotic programs. One program called entosis involves the invasion of live cells into their neighbors and is known to occur in cancers. Here, we identify a developmental function for entosis: to

Synthesis and evaluation of benzo[b]thiophene derivatives as inhibitors of alkaline phosphatases.

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

Synthesis and evaluation of thiophenyl derivatives as inhibitors of alkaline phosphatase.

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)

Nuclear-encoded mitochondrial ribosomal proteins are required to initiate gastrulation.

Agnes Cheong et al.

Development (Cambridge, England), 147(10) (2020-05-08)

Mitochondria are essential for energy production and although they have their own genome, many nuclear-encoded mitochondrial ribosomal proteins (MRPs) are required for proper function of the organelle. Although mutations in MRPs have been associated with human diseases, little is known

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Immunohistochemistry Procedure

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