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Merck
CN

190047

(−)-p-Bromolevamisole oxalate

99%

Synonym(s):

(−)-4-Bromotetramisole oxalate, 6-Bromolevamisole oxalate, S(−)-6-(4-Bromophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole oxalate

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About This Item

Empirical Formula (Hill Notation):
C11H11BrN2S · C2H2O4
CAS Number:
62284-79-1
Molecular Weight:
373.22
UNSPSC Code:
12352200
NACRES:
NA.06
PubChem Substance ID:
24278147
EC Number:
263-487-0
Beilstein/REAXYS Number:
4944883
MDL number:
MFCD00070406
Assay:
99%
Form:
powder

Key Documents

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InChI key

ZULBIBHDIQCNIS-HNCPQSOCSA-N

InChI

1S/C11H11BrN2S.C2H2O4/c12-9-3-1-8(2-4-9)10-7-14-5-6-15-11(14)13-10;3-1(4)2(5)6/h1-4,10H,5-7H2;(H,3,4)(H,5,6)/t10-;/m1./s1

SMILES string

OC(=O)C(O)=O.Brc1ccc(cc1)[C@H]2CN3CCSC3=N2

assay

99%

form

powder

optical activity

[α]25/D −104°, c = 0.5 in H2O

mp

192 °C (dec.) (lit.)

functional group

bromo, carboxylic acid, thioether

Quality Level

100

Related Categories

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT2912
MKCS3812
MKCL4198
MKCH8427
MKCG1780

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D E Amacher et al.
Enzyme, 42(1), 1-7 (1989-01-01)
Alkaline phosphatase (AP) from the sera of both male and female beagle dogs was partially purified and then analyzed for the presence of AP isoenzymes having intestinal or osseous characteristics as detected by bromotetramisole inhibition or wheat germ lectin agarose
M Onsgard-Meyer et al.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 213(2), 193-195 (1996-11-01)
Levamisole inhibits alkaline phosphatase (ALP) activity in kidney brush border membranes and increases phosphate excretion in vivo in dogs and rats. I-p-Bromotetramisole (I-BR) is a more potent analog of levamisole in regard to inhibition of ALP activity in vitro, but
S N Smith et al.
The American journal of physiology, 274(2 Pt 1), C492-C499 (1998-03-05)
Some cystic fibrosis transmembrane conductance regulator (CFTR) mutations, such as G551D, result in a correctly localized Cl- channel at the cell apical membrane, albeit with markedly reduced function. Patch-clamp studies have indicated that both phosphatase inhibitors and 3-isobutyl-1-methylxanthine (IBMX) can
F Becq et al.
The Journal of biological chemistry, 271(27), 16171-16179 (1996-07-05)
Patch-clamp, iodide efflux, and biochemical techniques were used to evaluate the ability of phenylimidazothiazoles to open normal and mutated cystic fibrosis transmembrane conductance regulator (CFTR) chloride channels and to investigate the mechanism of activation. As reported previously for bromotetramisole, levamisole
T Kuwana et al.
Journal of clinical pathology, 44(3), 236-237 (1991-03-01)
L-p-bromotetramisole was used to inhibit non-intestinal alkaline phosphatase (of liver or bone origin) (EC 3.1.3.1; ALP) in plasma, and intestinal ALP was measured from the uninhibited activity. The method of determination is convenient and correlated well with measurement by immunocapture
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