Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C11H16INO2 |
| Molecular Weight | 321.1547 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(I)=C(OC)C=C1CC(C)N
InChI
InChIKey=BGMZUEKZENQUJY-UHFFFAOYSA-N
InChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
2,5-Dimethoxy-4-iodoamphetamine (4-iodo-2,5-dimethoxyphenylisopropylamine or DOI), a psychedelic drug and hallucinogen has high affinity and is a potent agonist for each of the 5-HT2 receptor subtypes: 5-HT2A, 5-HT2B, and 5-HT2C. DOI's effects have been compared to LSD. DOI has a stereo center and R-(−)-DOI is the more active stereoisomer. It was shown, that R-(−)-DOI via 5-HT2A receptor could inhibit a variety of TNF-alpha-mediated proinflammatory markers, including intracellular adhesion molecule 1 (ICAM-1), vascular adhesion molecule 1 (VCAM-1), and interleukin (IL)-6 gene expression. It is known, that TNF-alpha-mediated inflammatory pathways have been strongly implicated in a number of diseases, including atherosclerosis, rheumatoid arthritis, psoriasis, type II diabetes, depression, schizophrenia, and Alzheimer's disease. Thus, because (R)-DOI can significantly inhibit the effects of TNF-alpha many hours after the administration of TNF-alpha, potential therapies could be aimed not only at preventing inflammation but at also treating the inflammatory injury that has already occurred or is ongoing.
Originator
Curator's Comment: Evan S. Herrmann, Patrick S. Johnson, Matthew W. Johnson, Ryan Vandrey. Neuropathology of Drug Addictions and Substance Misuse. Chapter 88 – Novel Drugs of Abuse: Cannabinoids, Stimulants, and Hallucinogens. 2016, Pages 893–902 retrieved from https://doi.org/10.1016/B978-0-12-800634-4.00088-3
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) |
0.7 nM [Ki] | ||
Target ID: P41595 Gene ID: 3357.0 Gene Symbol: HTR2B Target Organism: Homo sapiens (Human) |
20.0 nM [Ki] | ||
Target ID: P28335 Gene ID: 3358.0 Gene Symbol: HTR2C Target Organism: Homo sapiens (Human) |
2.4 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sample Use Guides
Trk receptors was identified as a downstream target of the hallucinogen 2,5-dimethoxy-4-iodoamphetamine hydrochloride (4-iodo-2,5-dimethoxyphenylisopropylamine or DOI). Treatment with DOI increased TrkA tyrosine phosphorylation in SK-N-SH cells, determined by immunoprecipitation with TrkA antibody and immunoblotting with anti-phosphotyrosine- and TrkA-antibodies. Analysis of DOI's effect on individual TrkA residues in SK-N-SH cells showed that it increases TrkA Tyr490 phosphorylation (177 ± 23% after 5 μM DOI for 30 min compared to vehicle). Furthermore, DOI treatment increased the percentage of SK-N-SH cells extending neurites in a TrkA-dependent manner (17.2 ± 2.2% after 5 μM DOI treatment for 6 days compared to 5.6 ± 1.7% after vehicle). In a different cell model-lymphoblastoid cell lines-DOI treatment increased tropomyosin-related kinase receptor B (TrkB) phosphorylation, determined by immunoprecipitation with TrkB antibody and immunoblotting with anti-phosphotyrosine antibody and total Trk antibody.
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WIKIPEDIA |
Designer-drugs-4-IODO-2,5-DIMETHOXYPHENYLISOPROPYLAMINE
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PiHKAL
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DTXSID7040520
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1229
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64629
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OOM10GW9UE
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2,5-DIMETHOXY-4-IODOAMPHETAMINE
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PRIMARY | 2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike other substituted amphetamines, however, it is not a stimulant.[2] DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer. In neuroscience research, [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of 5-HT2A serotonin receptors. DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience. | ||
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64584-34-5
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SALT/SOLVATE (PARENT)
SUBSTANCE RECORD
