Levamisole | CAS#14769-73-4

Levamisole
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318093

CAS#: 14769-73-4 (free base)

Description: Levamisole is a medication used to treat parasitic worm infections. It has also been studied as a method to stimulate the immune system as part of the treatment of cancer. Levamisole remains in veterinary use as a dewormer for livestock. It is on the World Health Organization's List of Essential Medicines.

Chemical Structure

Levamisole

CAS# 14769-73-4 (free base)

Instruction

Theoretical Analysis

MedKoo Cat#: 318093
Name: Levamisole
CAS#: 14769-73-4 (free base)
Chemical Formula: C11H12N2S
Exact Mass: 204.07
Molecular Weight: 204.291
Elemental Analysis: C, 64.67; H, 5.92; N, 13.71; S, 15.70

Price and Availability

Size	Price	Availability
1g	USD 300	2 Weeks
5g	USD 950	2 Weeks
10g	USD 1450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 14769-73-4 (free base) 16595-80-5 (HCl) 32093-35-9 (phosphate)

Synonym: Levamisole, Ergamisol, Decaris, Levotetramisole, Solaskil, Ketrax

IUPAC/Chemical Name: (6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

InChi Key: HLFSDGLLUJUHTE-SNVBAGLBSA-N

InChi Code: InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1

SMILES Code: C12=N[C@@H](C3=CC=CC=C3)CN1CCS2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 204.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Roberts JA, Chévez-Barrios P. Levamisole-Induced Vasculitis: A Characteristic Cutaneous Vasculitis Associated With Levamisole-Adulterated Cocaine. Arch Pathol Lab Med. 2015 Aug;139(8):1058-61. doi: 10.5858/arpa.2014-0107-RS. Review. PubMed PMID: 26230600.

2: Nolan AL, Jen KY. Pathologic manifestations of levamisole-adulterated cocaine exposure. Diagn Pathol. 2015 May 6;10:48. doi: 10.1186/s13000-015-0279-z. Review. PubMed PMID: 25943359; PubMed Central PMCID: PMC4419488.

3: Gaertner EM, Switlyk SA. Dermatologic complications from levamisole-contaminated cocaine: a case report and review of the literature. Cutis. 2014 Feb;93(2):102-6. Review. PubMed PMID: 24605347.

4: Tsai MH, Yang JH, Kung SL, Hsiao YP. Levamisole-induced myopathy and leukocytoclastic vasculitis: a case report and literature review. Dermatol Ther. 2013 Nov-Dec;26(6):476-80. doi: 10.1111/dth.12018. Epub 2013 Apr 1. Review. PubMed PMID: 24552411.

5: Magliocca KR, Coker NA, Parker SR. The head, neck, and systemic manifestations of levamisole-adulterated cocaine use. J Oral Maxillofac Surg. 2013 Mar;71(3):487-92. doi: 10.1016/j.joms.2012.10.028. Epub 2013 Jan 5. Review. PubMed PMID: 23298805.

6: Tran H, Tan D, Marnejon TP. Cutaneous vasculopathy associated with levamisole-adulterated cocaine. Clin Med Res. 2013 Feb;11(1):26-30. doi: 10.3121/cmr.2012.1085. Epub 2012 Jun 21. Review. PubMed PMID: 22723468; PubMed Central PMCID: PMC3573092.

7: Shea JL. Bioanalytical methods for quantitation of levamisole, a widespread cocaine adulterant. Clin Chem Lab Med. 2013 Jan;51(1):205-12. doi: 10.1515/cclm-2012-0519. Review. PubMed PMID: 23152411.

8: Arora NP. Cutaneous vasculopathy and neutropenia associated with levamisole-adulterated cocaine. Am J Med Sci. 2013 Jan;345(1):45-51. doi: 10.1097/MAJ.0b013e31825b2b50. Review. PubMed PMID: 23269350.

9: Dy IA, Wiernik PH. Cocaine-levamisole thrombotic vasculopathy. Semin Thromb Hemost. 2012 Nov;38(8):780-2. doi: 10.1055/s-0032-1328889. Epub 2012 Oct 6. Review. PubMed PMID: 23041983.

10: Martin RJ, Robertson AP, Buxton SK, Beech RN, Charvet CL, Neveu C. Levamisole receptors: a second awakening. Trends Parasitol. 2012 Jul;28(7):289-96. doi: 10.1016/j.pt.2012.04.003. Epub 2012 May 17. Review. PubMed PMID: 22607692; PubMed Central PMCID: PMC3378725.

11: Pearson T, Bremmer M, Cohen J, Driscoll M. Vasculopathy related to cocaine adulterated with levamisole: A review of the literature. Dermatol Online J. 2012 Jul 15;18(7):1. Review. PubMed PMID: 22863623.

12: Gulati S, Donato AA. Lupus anticoagulant and ANCA associated thrombotic vasculopathy due to cocaine contaminated with levamisole: a case report and review of the literature. J Thromb Thrombolysis. 2012 Jul;34(1):7-10. doi: 10.1007/s11239-012-0711-0. Review. PubMed PMID: 22437653.

13: Wolford A, McDonald TS, Eng H, Hansel S, Chen Y, Bauman J, Sharma R, Kalgutkar AS. Immune-mediated agranulocytosis caused by the cocaine adulterant levamisole: a case for reactive metabolite(s) involvement. Drug Metab Dispos. 2012 Jun;40(6):1067-75. doi: 10.1124/dmd.112.045021. Epub 2012 Mar 5. Review. PubMed PMID: 22393119.

14: Larocque A, Hoffman RS. Levamisole in cocaine: unexpected news from an old acquaintance. Clin Toxicol (Phila). 2012 Apr;50(4):231-41. doi: 10.3109/15563650.2012.665455. Review. Erratum in: Clin Toxicol (Phila). 2012 Jun;50(5):453. PubMed PMID: 22455354.

15: Ching JA, Smith DJ Jr. Levamisole-induced necrosis of skin, soft tissue, and bone: case report and review of literature. J Burn Care Res. 2012 Jan-Feb;33(1):e1-5. doi: 10.1097/BCR.0b013e318233fc64. Review. PubMed PMID: 22051802.

16: Buchanan JA, Lavonas EJ. Agranulocytosis and other consequences due to use of illicit cocaine contaminated with levamisole. Curr Opin Hematol. 2012 Jan;19(1):27-31. doi: 10.1097/MOH.0b013e32834da9ef. Review. PubMed PMID: 22143075.

17: de la Hera I, Sanz V, Cullen D, Chico R, Petiti G, Villar M, Burgués M, Sanz J, Castellanos M, Zarco O, Ortiz PL, Rodríguez-Peralto JL, Vanaclocha F. Necrosis of ears after use of cocaine probably adulterated with levamisole. Dermatology. 2011;223(1):25-8. doi: 10.1159/000329436. Epub 2011 Aug 16. Review. PubMed PMID: 21846960.

18: Martin RJ, Robertson AP. Mode of action of levamisole and pyrantel, anthelmintic resistance, E153 and Q57. Parasitology. 2007;134(Pt 8):1093-104. Review. PubMed PMID: 17608969.

19: Martin RJ, Verma S, Levandoski M, Clark CL, Qian H, Stewart M, Robertson AP. Drug resistance and neurotransmitter receptors of nematodes: recent studies on the mode of action of levamisole. Parasitology. 2005;131 Suppl:S71-84. Review. PubMed PMID: 16569294.

20: Davin JC, Merkus MP. Levamisole in steroid-sensitive nephrotic syndrome of childhood: the lost paradise? Pediatr Nephrol. 2005 Jan;20(1):10-4. Epub 2004 Sep 17. Review. PubMed PMID: 15378419.

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