Dexamisole | CAS#14769-74-5 | levamisole isomer

MedKoo Cat#: 461005 | Name: Dexamisole

Description:

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

Dexamisole is an inactive isomer of levamisole, a stereospecific inhibitor of ALP activity.

Chemical Structure

Dexamisole

CAS#14769-74-5 (free base)

Theoretical Analysis

MedKoo Cat#: 461005

Name: Dexamisole

CAS#: 14769-74-5 (free base)

Chemical Formula: C11H12N2S

Exact Mass: 204.0721

Molecular Weight: 204.29

Elemental Analysis: C, 64.67; H, 5.92; N, 13.71; S, 15.69

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

16595-76-9 (HCl) 14769-74-5 (free base)

Synonym

Dexamisole; d-Tetramisole; d Tetramisole

IUPAC/Chemical Name

(S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]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

Shelf Life

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

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

1: Bertucci C, Tedesco D, Fabini E, Di Pietra AM, Rossi F, Garagnani M, Del Borrello E, Andrisano V. Determination of levamisole and tetramisole in seized cocaine samples by enantioselective high-performance liquid chromatography and circular dichroism detection. J Chromatogr A. 2014 Oct 10;1363:150-4. doi: 10.1016/j.chroma.2014.07.069. Epub 2014 Jul 29. PubMed PMID: 25124228. 2: Casale JF, Colley VL, Legatt DF. Determination of phenyltetrahydroimidazothiazole enantiomers (Levamisole/Dexamisole) in illicit cocaine seizures and in the urine of cocaine abusers via chiral capillary gas chromatography-flame-ionization detection: clinical and forensic perspectives. J Anal Toxicol. 2012 Mar;36(2):130-5. doi: 10.1093/jat/bkr025. PubMed PMID: 22337783. 3: Dolezalová M, Tkaczyková M. LC determination of the enantiomeric purity of levamisole using stationary phase with bonded naphthylethylcarbamoylated-beta-cyclodextrin. J Pharm Biomed Anal. 2001 Jun;25(3-4):407-15. PubMed PMID: 11377020. 4: Anagnostou F, Plas C, Nefussi JR, Forest N. Role of beta-GP-derived Pi in mineralization via ecto-alkaline phosphatase in cultured fetal calvaria cells. J Cell Biochem. 1996 Aug;62(2):262-74. PubMed PMID: 8844406. 5: Anagnostou F, Plas C, Forest N. Ecto-alkaline phosphatase considered as levamisole-sensitive phosphohydrolase at physiological pH range during mineralization in cultured fetal calvaria cells. J Cell Biochem. 1996 Mar 15;60(4):484-94. PubMed PMID: 8707888. 6: Bellows CG, Aubin JE, Heersche JN. Initiation and progression of mineralization of bone nodules formed in vitro: the role of alkaline phosphatase and organic phosphate. Bone Miner. 1991 Jul;14(1):27-40. PubMed PMID: 1868267. 7: Granström G, Magnusson BC. Changes in alkaline-phosphatase isoenzymes of hard tissue origin during facial development in the rat. Arch Oral Biol. 1986;31(8):513-9. PubMed PMID: 3467674. 8: Lerner U, Granström G. Effect of levamisole on bone resorption in cultured mouse calvaria. Eur J Pharmacol. 1984 Oct 1;105(1-2):1-14. PubMed PMID: 6092109. 9: Adaikan PG, Zaman V. In vitro activity of anthelmintic drugs and biologically active substances on Breinlia booliati. Southeast Asian J Trop Med Public Health. 1982 Jun;13(2):257-61. PubMed PMID: 7147006. 10: Fallon MD, Whyte MP, Teitelbaum SL. Stereospecific inhibition of alkaline phosphatase by L-tetramisole prevents in vitro cartilage calcification. Lab Invest. 1980 Dec;43(6):489-94. PubMed PMID: 6449630. 11: Przegaliński E, Bigajska K, Siwanowicz J. Psychopharmacological profile of dexamisole. Pol J Pharmacol Pharm. 1980 Jan-Feb;32(1):21-9. PubMed PMID: 7454609. 12: Hozumi T, Iwaguchi T, Kitagawa H, Ozawa H. Anticancer activity of isomers of 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole. Gan. 1978 Jun;69(3):339-43. PubMed PMID: 669135. 13: Van Wauwe J, Van Nijen G. Effect of levamisole on autologous rosette-forming cells in nude mice. Clin Exp Immunol. 1977 Dec;30(3):465-8. PubMed PMID: 304789; PubMed Central PMCID: PMC1541137. 14: Vanhoutte PM, Van Nueten JM, Verbeuren TJ, Laduron PM. Differential effects of the isomers of tetramisole on adrenergic neurotransmission in cutaneous veins of dog. J Pharmacol Exp Ther. 1977 Jan;200(1):127-40. PubMed PMID: 189006.