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L9756 Sigma

(−)-Tetramisole hydrochloride

≥99% (GC)

Synonym: (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

  • CAS Number 16595-80-5

  • Empirical Formula (Hill Notation) C11H12N2S · HCl

  • Molecular Weight 240.75

  •  Beilstein Registry Number 4358988

  •  EC Number 240-654-6

  •  MDL number MFCD00012675

  •  PubChem Substance ID 24278526

  • Popular Documents:  FTNMR (PDF)  

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Description

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.1 Very effective in treatment of ascariasis (hookworm infestation).2 Useful in chemotherapy of colorectal cancers, possibly due to its stimulation of IL-1 production and direct activation of macrophages.3

Packaging

5, 10 g in poly bottle

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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.

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
25
Safety Statements (Europe) 
36/37/39-45
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
NJ5960000

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. The general immunopharmacology of levamisole Renoux, G. Drugs 20, 89-99, (1980)

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2. Use of levamisole in parasitic infections Miller, M.J. Drugs 20, 122-130, (1980)

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3. Experimental modulation of IL-1 production and cell surface molecule expression by levamisole Kimball, E.S. Ann. N. Y. Acad. Sci. 685, 259-268, (1993)

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Kinetics and inhibition of alkaline phosphatases from canine tissues. Van Belle, H. Biochim. Biophys. Acta 289, 158, (1972)

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Matrix gla protein and alkaline phosphatase are differently modulated in human dermal fibroblasts from PXE patients and controls. Boraldi F, Annovi G, Vermeer C, et al. J. Invest. Dermatol. 133(4), 946-54, (2013)

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Expression of cyclin D1a and D1b as predictive factors for treatment response in colorectal cancer. Myklebust MP, Li Z, Tran TH, et al. Br. J. Cancer 107(10), 1684-91, (2012)

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Facial cutaneous necrosis associated with suspected levamisole toxicity from tainted cocaine abuse. Formeister EJ, Falcone MT, and Mair EA Ann. Otol. Rhinol. Laryngol. 124(1), 30-4, (2015)

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Cocaine-induced recurrent leukoencephalopathy. González-Duarte A and Williams R Neuroradiol. J. 26(5), 511-3, (2013)

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[Bilateral necrosis of earlobes induced by cocaine]. Bodro M, Vidaller A, del Castillo N, et al. Med. Clin. (Barc.) 140(5), e9, (2013)

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[Determination of levamisole residue in animal livers by two liquid-liquid extraction steps-gas chromatography-mass spectrometry]. Xu J, Xiao S, Dong W, et al. Se Pu 30(9), 922-5, (2012)

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Levamisole-induced leukocytoclastic vasculitis and neutropenia in a patient with cocaine use: an extensive case with necrosis of skin, soft tissue, and cartilage. Arora NP, Jain T, Bhanot R, et al. Addict. Sci. Clin. Pract. 7(1), 19, (2012)

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Phenotypic Characterization of Two Ancylostoma caninum Isolates with Different Susceptibilities to the Anthelmintic Pyrantel Steven R. Kopp, Glen T. Coleman, et al. Antimicrob. Agents Chemother. 52, 3980-3986, (2008)

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Rheumatic manifestations of cocaine use. Graf J Curr. Opin. Rheumatol. 25(1), 50-5, (2013)

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Synthesis and evaluation of thiophenyl derivatives as inhibitors of alkaline phosphatase. Lei Chang et al Bioorg. Med. Chem. Lett. 21, 2297-301, (2011)

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Synthesis and antiangiogenic activity of N-alkylated levamisole derivatives. Hansen AN, Bendiksen CD, Sylvest L, et al. PLoS ONE 7(9), e45405, (2012)

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Synthesis and evaluation of benzo[b]thiophene derivatives as inhibitors of alkaline phosphatases. Lina Li et al Bioorg. Med. Chem. 17, 7290-300, (2009)

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TNAP and EHD1 are over-expressed in bovine brain capillary endothelial cells after the re-induction of blood-brain barrier properties. Deracinois B, Duban-Deweer S, Pottiez G, et al. PLoS ONE 7(10), e48428, (2012)

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Development and evaluation of age-appropriate film-coated tablets of levamisole for paediatric use (2 - 18 years). Kreeftmeijer-Vegter AR, de Meijer M, Wegman KA, et al. Expert Opin. Drug Deliv. 10(3), 293-300, (2013)

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Pharmacological assays reveal age-related changes in synaptic transmission at the Caenorhabditis elegans neuromuscular junction that are modified by reduced insulin signalling. Mulcahy B, Holden-Dye L, and O'Connor V J. Exp. Biol. 216(Pt 3), 492-501, (2013)

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Prevalence of gastrointestinal helminths and anthelmintic resistance on small-scale farms in Gauteng Province, South Africa. Tsotetsi AM, Njiro S, Katsande TC, et al. Trop. Anim. Health Prod. 45(3), 751-61, (2013)

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Leishmania amazonensis: characterization of an ecto-pyrophosphatase activity. Freitas-Mesquita AL, Fonseca-de-Souza AL, and Meyer-Fernandes JR Exp. Parasitol. 137, 8-13, (2014)

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The head, neck, and systemic manifestations of levamisole-adulterated cocaine use. Magliocca KR, Coker NA, and Parker SR J. Oral Maxillofac. Surg. 71(3), 487-92, (2013)

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A promising immunosuppressive strategy of cyclosporine alternately combined with levamisole is highly effective for moderate aplastic anemia. Li X, Shao Y, Ge M, et al. Ann. Hematol. 92(9), 1239-47, (2013)

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Efficacy of decoquinate against Sarcocystis neurona in cell cultures. Lindsay DS, Nazir MM, Maqbool A, et al. Vet. Parasitol. 196(1-2), 21-3, (2013)

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Anthelmintic and antimicrobial activity of methanolic and aqueous extracts of Euphorbia helioscopia L. Lone BA, Bandh SA, Chishti MZ, et al. Trop. Anim. Health Prod. 45(3), 743-9, (2013)

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Levamisole toxicity mimicking autoimmune disease. Strazzula L, Brown KK, Brieva JC, et al. J. Am. Acad. Dermatol. 69(6), 954-9, (2013)

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Illicit drugs: What dermatologists need to know. Hennings C and Miller J J. Am. Acad. Dermatol. 69(1), 135-42, (2013)

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Synergistic and additive effects of cimetidine and levamisole on cellular immune responses to hepatitis B virus DNA vaccine in mice. Niu X, Yang Y, and Wang J Scand. J. Immunol. 77(2), 84-91, (2013)

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Cocaine-levamisole thrombotic vasculopathy. Dy IA and Wiernik PH Semin. Thromb. Hemost. 38(8), 780-2, (2012)

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Effects of levamisole and ranitidine on antibody-forming responses induced by killed Mycoplasma vaccine antigens in Saanen goats. Temizel EM, Onat K, Mecitoglu Z, et al. Vet. Rec. 171(23), 597, (2012)

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Trypanosoma rangeli: an alkaline ecto-phosphatase activity is involved with survival and growth of the parasite. Dos-Santos AL, Dick CF, Silveira TS, et al. Exp. Parasitol. 135(2), 459-65, (2013)

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In vitro anthelmintic activity of aqueous leaf extract of Annona muricata L. (Annonaceae) against Haemonchus contortus from sheep. Ferreira LE, Castro PM, Chagas AC, et al. Exp. Parasitol. 134(3), 327-32, (2013)

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Cutaneous vasculopathy and neutropenia associated with levamisole-adulterated cocaine. Arora NP Am. J. Med. Sci. 345(1), 45-51, (2013)

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Small vessel vasculitis associated with cocaine use. Rietkerk W, Pereira F, and Poste J Cutis. 91(1), 21-4, (2013)

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Determination of levamisole in the plasma of patients with falciparum malaria using high-performance liquid chromatography. Chiadmi F and Schlatter J Clin. Lab. 59(3-4), 439-44, (2013)

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Superior efficacy of azithromycin and levamisole vs. azithromycin in the treatment of inflammatory acne vulgaris: an investigator blind randomized clinical trial on 169 patients. Rassai S, Mehri M, Yaghoobi R, et al. Int. J. Clin. Pharmacol. Ther. 51(6), 490-4, (2013)

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Cocaine abuse and confidentiality: a case of retiform purpura in an adolescent patient. Streicher JL, Swerlick RA, and Stoff BK J. Am. Acad. Dermatol. 70(6), 1127-9, (2014)

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Levamisole-induced vasculopathy: staging and management. Gillis JA, Green P, and Williams J J. Plast. Reconstr. Aesthet. Surg. 67(1), e29-31, (2014)

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Reticular rash, cocaine, and levamisole. Petrosyan F Mayo Clin. Proc. 88(2), e19, (2013)

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Re: levamisole-adulterated cocaine: a case series. Lott JP J. Am. Board Fam. Med. 26(1), 98, (2013)

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Levamisole toxicity. Graebner RW Mayo Clin. Proc. 87(10), 1033-4; author reply 1034, (2012)

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