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Merck

L9756

(−)-Tetramisole hydrochloride

powder, ≥99% (GC)

Synonyme(s) :

(S)-(−)-6-phényl-2,3,5,6-tétrahydroimidazo[2,1-b]thiazole hydrochloride, L(−)-2,3,5,6-tétrahydro-6-phénylimidazo(2,1-b)thiazole hydrochloride

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A propos de cet article

Formule empirique (notation de Hill) :
C11H12N2S · HCl
Numéro CAS:
16595-80-5
Poids moléculaire :
240.75
NACRES:
NA.77
PubChem Substance ID:
24278526
UNSPSC Code:
12352202
EC Number:
240-654-6
MDL number:
MFCD00012675
Beilstein/REAXYS Number:
4358988

Principaux documents

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Nom du produit

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

InChI key

LAZPBGZRMVRFKY-HNCPQSOCSA-N

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

SMILES string

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

biological source

synthetic (organic)

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

Quality Level

200

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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

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
0000435886
0000435908
0000435908
0000435886
0000433184

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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
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
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
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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