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D101

Sigma-Aldrich

(±)-DOI hydrochloride

≥98% (HPLC), solid,  5-HT2 serotonin receptor agonist

Synonym(s):

(±)-1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane hydrochloride, (±)-2,5-Dimethoxy-4-iodoamphetamine hydrochloride, (±)-DOI

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About This Item

Empirical Formula (Hill Notation):
C11H16INO2 · HCl
CAS Number:
42203-78-1
Molecular Weight:
357.62
MDL number:
MFCD00055199
UNSPSC Code:
12352200
PubChem Substance ID:
24278092
NACRES:
NA.77

product name

(±)-DOI hydrochloride, ≥98% (HPLC), solid

Quality Level

100

Assay

≥98% (HPLC)

form

solid

drug control

Home Office Schedule 1; regulated under CDSA - not available from Sigma-Aldrich Canada

color

white to off-white

solubility

H2O: 10 mg/mL
ethanol: 2 mg/mL

SMILES string

NC(C)CC1=CC(OC)=C(I)C=C1OC.Cl

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

InChI key

QVFDMWGKHUFODK-UHFFFAOYSA-N

Gene Information

human ... HTR2A(3356) , HTR2B(3357) , HTR2C(3358)

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Biochem/physiol Actions

(±)-DOI hydrochloride is a potent and selective 5-HT2 serotonin receptor agonist that crosses the blood-brain barrier, increases dopamine turnover and the treatment with DOI counteracted the expression of the nicotine-induced locomotor and neurochemical sensitization, but had no effect on nicotine-induced behavioral disinhibition. The responses to DOI provide evidence that of these receptors are abundant in the cortex, and show relatively lower levels in hippocampus and cerebellum.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J Ichikawa et al.
Brain research, 698(1-2), 204-208 (1995-11-06)
The effects of (+-)-DOI (1-(2,5-dimethoxy-4-iodophenyl)-aminopropane) hydrochloride, a mixed 5-HT2A/2C receptor agonist, on the release of dopamine (DA) following D-amphetamine sulfate (AMP) or a DA D2 autoreceptor selective dose of (-)-apomorphine hydrochloride (APO), were investigated in rat striatum (STR) and nucleus
G J Marek et al.
The Journal of pharmacology and experimental therapeutics, 278(3), 1373-1382 (1996-09-01)
Correlations between 5-hydroxytryptamine (5-HT) receptor binding affinities and human hallucinogenic potency have suggested that 5-HT2 receptors mediate the hallucinogenic effects of lysergic acid diethylamide (LSD) and phenethylamine hallucinogens. Electrophysiological studies have suggested that a subpopulation of gamma-aminobutyric acid (GABA)ergic interneurons
R Gaggi et al.
General pharmacology, 28(4), 583-587 (1997-04-01)
1. The behavioral responses, as well as the biogenic amines and metabolite contents in discrete brain areas were determined in male rats subcutaneously treated with a 5-HT1A (8-OHDPAT) or 5-HT2A (DOI) agonist at doses (0.5-2 mg/kg) sufficient to produce the
Jingya Ruan et al.
Molecules (Basel, Switzerland), 25(17) (2020-08-28)
Yucca schidigera Roezl (Mojave), a kind of ornamental plant belonging to the Yucca genus (Agavaceae), whose extract exhibits important roles in food, beverage, cosmetic and feed additives owing to its rich spirostanol saponins. To provide a comprehensive chemical profiling of
Joe Anand Kumar John Jayakumar et al.
Scientific reports, 10(1), 21675-21675 (2020-12-12)
5-HT2A, a G-protein coupled receptor, is widely expressed in the human body, including in the gastrointestinal tract, platelets and the nervous system. It mediates various functions, for e.g. learning, memory, mood regulation, platelet aggregation and vasoconstriction, but its involvement in

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