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1-Iodomorphine
Sign in to save1-Iodomorphine is a semi-synthetic narcotic analgesic formed by halogenation of the 1 position on the morphine carbon skeleton. Halogenated morphine derivatives were first synthesised in Germany, Austria/Austria-Hungary, the United Kingdom and the United States in the period 1890 to 1930. Use of this drug increased after 1945 for the below-mentioned research. It is a research chemical which is often prepared in the laboratory when it is needed.
Chemical data
- Formula
- C17H18INO3
- Molecular weight
- 411.23 g/mol
- IUPAC name
- (4R,4aR,7S,7aR,12bS)-11-iodo-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
- SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C(C=C(C(=C52)O[C@H]3[C@H](C=C4)O)O)I
- InChIKey
- YFXOJQFZAJTGHD-GLWLLPOHSA-N
- XLogP
- 1.4
- Polar surface area
- 52.9 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 411.033141436
Show 4 more facts
- chemical formula
- C₁₇H₁₈INO₃
- isomeric SMILES
- O[C@H]1\C=C/[C@H]4[C@H]2Cc5c3c(O[C@@H]1[C@]34CCN2C)c(O)cc5I
- Commons category
- 1-Iodomorphine
- canonical SMILES
- CN1CCC23c4c5c(I)cc(O)c4OC2C(O)C=CC3C1C5
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
1-Iodomorphine is a semi-synthetic narcotic analgesic formed by halogenation of the 1 position on the morphine carbon skeleton. Halogenated morphine derivatives were first synthesised in Germany, Austria/Austria-Hungary, the United Kingdom and the United States in the period 1890 to 1930. Use of this drug increased after 1945 for the below-mentioned research. It is a research chemical which is often prepared in the laboratory when it is needed.
Along with the similar 2-iodomorphine as well as iodinated analogs of dihydromorphine, dihydrocodeine, heroin, and the fluorinated, chlorinated, and brominated analogues of this series, this change may not impact the activity of the drug to a notable extent but 1- and 2-iodomorphine are used in pharmacological, neurological, metabolic, and endocrine research as it allows the tagging of morphine with iodine-131 or iodine-129. Such research was important in the discovery of opioid receptors in the central nervous system, peripheral nervous system, and other tissues in humans, mammals, birds, and some reptiles, amphibians, fish, insects, and arthropods.
Excerpted from Wikipedia’s “1-Iodomorphine” article, available under the CC BY-SA 4.0 licence.