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L9756

Sigma-Aldrich

(−)-Tetramisole hydrochloride

≥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

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

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

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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Chemosphere, 261, 127756-127756 (2020-07-31)
Urgent need for treatments limit studies of therapeutic drugs before approval by regulatory agencies. Analyses of drugs after approval can therefore improve our understanding of their mechanism of action and enable better therapies. We screened a library of 1443 Food
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
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