D101

Sigma-Aldrich

(±)-DOI hydrochloride

≥98% (HPLC), solid

Synonym(s):
(±)-2,5-Dimethoxy-4-iodoamphetamine hydrochloride, (±)-1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane hydrochloride, (±)-DOI
Empirical Formula (Hill Notation):
C11H16INO2 · HCl
CAS Number:
Molecular Weight:
357.62
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

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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Packaging

25 mg in poly bottle
10 mg in glass bottle
100, 500 mg in glass bottle

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...

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