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D101

(±)-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
UNSPSC Code:
12352200
PubChem Substance ID:
24278092
NACRES:
NA.77
MDL number:
MFCD00055199
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
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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, kontrollierte Droge in Deutschland

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)

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.

Legal Information

German
Dieses Produkt fällt unter das Betäubungsmittelgesetz (BtMG). Für eine Bestellung dieses Produktes ist eine Erlaubnis nach § 3 BtMG zwingend erforderlich, es sei denn, es greift eine Ausnahme von der Erlaubnispflicht nach § 4 oder § 26 BtMG.

English
This product is subject to the German Narcotics Act. A permit under Section 3 of the German Narcotics Act is mandatory for ordering this product unless an exemption from the permit requirement under Section 4 or Section 26 of the German Narcotics Act applies.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000546555
0000546554
0000546553
0000546552
0000546555

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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
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