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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
Structure of DOI HYDROCHLORIDE

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

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 ( + / - )

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

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
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 09:14:58 GMT 2023
Edited
by admin
on Sat Dec 16 09:14:58 GMT 2023
Record UNII
Q2E57V2WS3
Record Status Validated (UNII)
Record Version
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Name Type Language
DOI HYDROCHLORIDE
Common Name English
(±)-2,5-DIMETHOXY-4-IODOAMPHETAMINE HYDROCHLORIDE
Systematic Name English
(±)-1-(2,5-DIMETHOXY-4-IODOPHENYL)-2-AMINOPROPANE HYDROCHLORIDE
Systematic Name English
4-IODO-2,5-DIMETHOXYPHENYLISOPROPYLAMINE HYDROCHLORIDE
Systematic Name English
BENZENEETHANAMINE, 4-IODO-2,5-DIMETHOXY-.ALPHA.-METHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
DOI HCL
Common Name English
2,5-Dimethoxy-4-iodoamphetamine hydrochloride
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID50962366
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
FDA UNII
Q2E57V2WS3
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
PUBCHEM
170617
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
CAYMAN
13885
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
CAS
42203-78-1
Created by admin on Sat Dec 16 09:14:58 GMT 2023 , Edited by admin on Sat Dec 16 09:14:58 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE