3-Iodobenzylguanidine
Basic information
- CAS
80663-95-2- Standard SMILES
NC(N)=NCc1cccc(I)c1- InChIKey
PDWUPXJEEYOOTR-UHFFFAOYSA-N- Molecular formula
- C8H10IN3
- Average molar mass
- 275.09 g/mol
- Monoisotopic mass
- 274.99194
Overview
2-[(3-iodophenyl)methyl]guanidine is an organoiodine compound.
Names & identifiers
- Preferred name
- 3-Iodobenzylguanidine
- IUPAC
- 2-[(3-iodophenyl)methyl]guanidine
- English name
- Caindexname:guanidine,[(3-iodophenyl)methyl]
- Molecular formula
- C8H10IN3
- Molecular weight
- 275.09
Names & synonyms
3-Iodobenzylguanidinem Iodobenzylguanidine3 Iodobenzylguanidinemeta IodobenzylguanidineRefChem:94458123I Labeled 3-Iodobenzylguanidine125I Labeled 3-Iodobenzylguanidine3 Iodobenzylguanidine, 123I Labeled3 Iodobenzylguanidine, 125I LabeledIobenguane80663-95-21-(3-Iodobenzyl)guanidine
Show more names
Iobenguane sulfateM-iodobenzylguanidine hemisulfateIobenguane-d413C,15N2]-IobenguaneN-[(3-iodophenyl)methyl]GuanidineGuanidine, N-[(3-iodophenyl)methyl]-m-Iodobenzoylguanidine Hemisulfate SaltCaindexname:guanidine,[(3-iodophenyl)methyl]m-Iodobenzylguanidine hemisulphate salt, ≥98%
m-IodobenzylguanidineMetaiodobenzylguanidine2-[(3-iodophenyl)methyl]guanidineGuanidine,N-[(3-iodophenyl)methyl]-MIBGmeta-IodobenzylguanidineMFCD00133520Iobenguane (127-i)
Database identifiers
- CAS
80663-95-2- PubChem CID
- 60860
- DTXSID
DTXSID4048438- ChEMBL
CHEMBL818- ChEBI
CHEBI:92769- UNII
- 35MRW7B4AD
- EC Number
- 688-301-9
- Nikkaji
- J360.168D
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 64.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 166
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SolubilitySoluble
Human DrugsBreast Feeding; Lactation; Milk, Human; Radiopharmaceuticals; Iodine Radioisotopes; Diagnostic Agents
Boiling Point100°C
Melting Point0°C
Physicochemical properties
- Boiling point
- 351.3 · 351.3±52.0 °C(Predicted)
- Density
- 1.85 · 1.85±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 12.43 · 12.43±0.70(Predicted)
- Appearance
- White to off-white Solid
- CAS DataBase Reference
- 80663 · 80663-95-2
- FDA UNII
- 35 MRW7B4AD · 35MRW7B4AD
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- hs_code
- 29252900
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Pharmacodynamics
AdreView is a diagnostic radiopharmaceutical which contains a small quantity of iobenguane that is not expected to produce a pharmacodynamic effect. Patients with renal insufficiency may experience increased radiation exposure and impaired imaging results.
Mechanism of Action
Structure of iobenguane is similar to noradrenaline so it can be taken up by adrenergic tissue in the adrenal medulla, liver, heart, and spleen. Once taken up by noradrenaline transporters in the adrenergic nerve terminals, it is stored in the presynaptic storage vesicles. The radioactive iodine component is responsible for its imaging properties.
Biological Half-LifePhysical half life = 13.2 hours
Metabolism/MetabolitesLess than 10% of the dose is metabolized into m-iodohippuric acid (MIHA). However the mechanism in which this metabolite is produced is unknown.
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Compounds that are used in medicine as sources of radiation for radiotherapy and for diagnostic purposes. They have numerous uses in research and industry. (Martindale, The Extra Pharmacopoeia, 30th ed, p1161)
Absorption, Distribution and Excretion
Iobenguane rapidly clears from the blood and is highly retained in adrenergic tissues.
Renally excreted unchanged (70%-90%) via glomerular filtration; Fecal (<1%)
Applications
Usesm-Iodobenzylguanidine Hemisulfatecan be used to demethylate and oxidize membrane-associated DNA. It has also been employed to develop a cell-based high-throughput screening assay to identify anti-hepatitis C virus compounds.
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Compound notes
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