Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C11H16INO2.ClH |
| Molecular Weight | 357.616 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=CC(I)=C(OC)C=C1CC(C)N
InChI
InChIKey=QVFDMWGKHUFODK-UHFFFAOYSA-N
InChI=1S/C11H16INO2.ClH/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2;/h5-7H,4,13H2,1-3H3;1H
| Molecular Formula | C11H16INO2 |
| Molecular Weight | 321.1547 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| 5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA). | 1984 Jun 15 |
|
| Differentiation of 5-hydroxytryptamine2 receptor subtypes using 125I-R-(-)2,5-dimethoxy-4-iodo-phenylisopropylamine and 3H-ketanserin. | 1989 Oct |
|
| The hallucinogen 2,5-dimethoxy-4-iodoamphetamine hydrochloride activates neurotrophin receptors in a neuronal cell line and promotes neurites extension. | 2017 Jun |
|
| Influence of intertrial interval on basal and drug-induced impulsive action in the 5-choice serial reaction time task: Effects of d-amphetamine and (±)-2,5-dimethoxy-4-iodoamphetamine (DOI). | 2018 Jan 1 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:14:58 UTC 2023
by
admin
on
Sat Dec 16 09:14:58 UTC 2023
|
| Record UNII |
Q2E57V2WS3
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID50962366
Created by
admin on Sat Dec 16 09:14:58 UTC 2023 , Edited by admin on Sat Dec 16 09:14:58 UTC 2023
|
PRIMARY | |||
|
Q2E57V2WS3
Created by
admin on Sat Dec 16 09:14:58 UTC 2023 , Edited by admin on Sat Dec 16 09:14:58 UTC 2023
|
PRIMARY | |||
|
170617
Created by
admin on Sat Dec 16 09:14:58 UTC 2023 , Edited by admin on Sat Dec 16 09:14:58 UTC 2023
|
PRIMARY | |||
|
13885
Created by
admin on Sat Dec 16 09:14:58 UTC 2023 , Edited by admin on Sat Dec 16 09:14:58 UTC 2023
|
PRIMARY | |||
|
42203-78-1
Created by
admin on Sat Dec 16 09:14:58 UTC 2023 , Edited by admin on Sat Dec 16 09:14:58 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
|
