I8250
3-Iodo-L-tyrosine
Tyrosine hydroxylase inhibitor
Synonym(s):
3-Monoiodo-L-tyrosine
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About This Item
Linear Formula:
IC6H3-4-(OH)CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
307.09
NACRES:
NA.32
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352200
EC Number:
200-744-8
MDL number:
Beilstein/REAXYS Number:
2941266
Product Name
3-Iodo-L-tyrosine,
InChI key
UQTZMGFTRHFAAM-ZETCQYMHSA-N
InChI
1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1
SMILES string
N[C@@H](Cc1ccc(O)c(I)c1)C(O)=O
impurities
~5% tyrosine
mp
210 °C (dec.) (lit.)
solubility
dilute aqueous acid: soluble
storage temp.
−20°C
Quality Level
Gene Information
human ... TH(7054)
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Application
3-Iodo-L-tyrosine has been used as an inhibitor for tyrosine hydroxylase enzyme in Drosophila and silkworm pupae.
Biochem/physiol Actions
3-iodotyrosine (3-IY) inhibits tyrosine hydroxylase that catalyzes levodopa (L-DOPA) formation from tyrosine. Iodotyrosine deiodinase enzyme deficiency leads to elevated levels of 3-IY in serum and urine in severe hypothyroidism and goiter.
TH (tyrosine 3-hydroxylase) is responsible for catalyzing the first step of the noradrenergic biosynthesis pathway. Mutations in TH are associated with tyrosine hydroxylase deficiency, leading to conditions such as infantile parkinsonism and DOPA (dopamine)-responsive dystonia as well as encephalopathy with perinatal onset.
Tyrosine hydroxylase inhibitor.
General description
Iodotyrosine coupled with di-iodotyrosine results in the synthesis of 3,5,3′-tri-iodothyronine (T3) or 3,3′,5′-tri-iodothyronine (rT3).
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Jacqueline Studer et al.
Journal of forensic sciences, 59(6), 1650-1653 (2014-07-01)
Catecholamines, especially noradrenalin, are essential in the control of respiration and arousal. Thus, an impaired production of these neurotransmitters may contribute to the occurrence of sudden infant death syndrome (SIDS). The first step of the noradrenergic synthesis pathway is catalyzed
D K Ness et al.
Fundamental and applied toxicology : official journal of the Society of Toxicology, 30(2), 153-161 (1996-04-01)
Planarians (Dugesia dorotocephala) were evaluated as bioassay organisms to detect inhibition of tyrosine hydroxylase, the rate-limiting enzyme in the synthesis of catecholamines. Thirty planaria per dose were exposed to 0 (control), 0.001, 0.01, 0.1, or 1 mM 3-iodo-L-tyrosine (monoiodotyrosine or
L G Harsing et al.
Neuroscience, 77(2), 419-429 (1997-03-01)
Striatal slices from the rat were preincubated with [3H]GABA and superfused in the presence of nipecotic acid and aminooxyacetic acid, inhibitors of high-affinity GABA transport and GABA aminotransferase, respectively. GABA efflux was estimated by monitoring tritium efflux, 98% of which
A new brain dopamine-deficient Drosophila and its pharmacological and genetic rescue
Cichewicz K, et al.
Genes, Brain, and Behavior, 16(3), 394-403 (2017)
Anionic iodotyrosine residues are required for iodothyronine synthesis
De Vijlder JJ and den Hartog MT
European Journal of Endocrinology, 138(2), 227-231 (1998)
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