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D101

Sigma-Aldrich

(±)-DOI hydrochloride

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

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C11H16INO2 · HCl
Číslo CAS:
42203-78-1
Molekulová hmotnost:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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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
Jingya Ruan et al.
Molecules (Basel, Switzerland), 25(17) (2020-08-28)
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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
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
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Scientific reports, 10(1), 21675-21675 (2020-12-12)
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