DOI HYDROCHLORIDE

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 Search

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	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9933142 | https://www.ncbi.nlm.nih.gov/pubmed/18708586

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
5-hydroxytryptamine receptor 2A 73 Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9933142/	Agonist 2752	0.7 nM [Ki]
5-hydroxytryptamine receptor 2B 12 Target ID: P41595 Gene ID: 3357.0 Gene Symbol: HTR2B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9933142/	Agonist 2752	20.0 nM [Ki]
5-hydroxytryptamine receptor 2C 29 Target ID: P28335 Gene ID: 3358.0 Gene Symbol: HTR2C Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9933142/	Agonist 2752	2.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
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).	2018-01-01	29102783
The hallucinogen 2,5-dimethoxy-4-iodoamphetamine hydrochloride activates neurotrophin receptors in a neuronal cell line and promotes neurites extension.	2017-06	28315978
Differentiation of 5-hydroxytryptamine2 receptor subtypes using 125I-R-(-)2,5-dimethoxy-4-iodo-phenylisopropylamine and 3H-ketanserin.	1989-10	2795135
5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA).	1984-06-15	6479216

Sample Use Guides

In Vivo Use Guide

hallucinogen: 1.5 - 3.0 mg

Route of Administration: Oral

In Vitro Use Guide

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 `Mon Mar 31 22:35:21 GMT 2025` Edited by `admin` on `Mon Mar 31 22:35:21 GMT 2025`
Record UNII	Q2E57V2WS3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-1-(2,5-DIMETHOXY-4-IODOPHENYL)-2-AMINOPROPANE HYDROCHLORIDE

Preferred Name

English

DOI HYDROCHLORIDE

Common Name

English

(±)-2,5-DIMETHOXY-4-IODOAMPHETAMINE 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