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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
Structure of DOI

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

HIDE SMILES / InChI

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 ( + / - )

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

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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

hallucinogen: 1.5 - 3.0 mg
Route of Administration: Oral
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 Sat Dec 16 08:11:46 GMT 2023
Edited
by admin
on Sat Dec 16 08:11:46 GMT 2023
Record UNII
OOM10GW9UE
Record Status Validated (UNII)
Record Version
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Name Type Language
DOI
Common Name English
(±)-DOI
Common Name English
(±)-1-(4-IODO-2,5-DIMETHOXYPHENYL)-2-AMINOPROPANE
Systematic Name English
BENZENEETHANAMINE, 4-IODO-2,5-DIMETHOXY-.ALPHA.-METHYL-
Systematic Name English
J246.190K
Code English
2,5-DIMETHOXY-4-IODOAMPHETAMINE
Systematic Name English
4-IODO-2,5-DIMETHOXYPHENYLISOPROPYLAMINE
Systematic Name English
(±)-1-(2,5-DIMETHOXY-4-IODOPHENYL)-2-AMINOPROPANE
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-4-IODO-2,5-DIMETHOXYPHENYLISOPROPYLAMINE
Created by admin on Sat Dec 16 08:11:46 GMT 2023 , Edited by admin on Sat Dec 16 08:11:46 GMT 2023
WIKIPEDIA PiHKAL
Created by admin on Sat Dec 16 08:11:46 GMT 2023 , Edited by admin on Sat Dec 16 08:11:46 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID7040520
Created by admin on Sat Dec 16 08:11:46 GMT 2023 , Edited by admin on Sat Dec 16 08:11:46 GMT 2023
PRIMARY
PUBCHEM
1229
Created by admin on Sat Dec 16 08:11:46 GMT 2023 , Edited by admin on Sat Dec 16 08:11:46 GMT 2023
PRIMARY
CHEBI
64629
Created by admin on Sat Dec 16 08:11:46 GMT 2023 , Edited by admin on Sat Dec 16 08:11:46 GMT 2023
PRIMARY
FDA UNII
OOM10GW9UE
Created by admin on Sat Dec 16 08:11:46 GMT 2023 , Edited by admin on Sat Dec 16 08:11:46 GMT 2023
PRIMARY
WIKIPEDIA
2,5-DIMETHOXY-4-IODOAMPHETAMINE
Created by admin on Sat Dec 16 08:11:46 GMT 2023 , Edited by admin on Sat Dec 16 08:11:46 GMT 2023
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.
CAS
64584-34-5
Created by admin on Sat Dec 16 08:11:46 GMT 2023 , Edited by admin on Sat Dec 16 08:11:46 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ACTIVE ENANTIOMER->RACEMATE
ENANTIOMER -> RACEMATE
LABELED -> NON-LABELED
TARGET->PARTIAL AGONIST
TARGET -> INHIBITOR
BINDING
IC50
TARGET -> INHIBITOR
BINDING
IC50