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D153

Sigma-Aldrich

(R)(−)-DOI hydrochloride

≥98% (HPLC), solid

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C11H16INO2 · HCl
CAS-Nummer:
82864-02-6
Molekulargewicht:
357.62
MDL-Nummer:
MFCD00153796
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24278404
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

solid

Optische Aktivität

[α]22/D −12.36°, c = 2 in H2O(lit.)

drug control

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

Farbe

white

Löslichkeit

H2O: ≥20 mg/mL
ethanol: soluble

SMILES String

Cl.COc1cc(C[C@@H](C)N)c(OC)cc1I

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/t7-;/m1./s1

InChIKey

QVFDMWGKHUFODK-OGFXRTJISA-N

Angaben zum Gen

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

Biochem./physiol. Wirkung

Potent and selective 5-HT2 serotonin receptor agonist that crosses the blood-brain barrier; more potent enantiomer of ±-DOI hydrochloride.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Ishier Raote et al.
Molecular pharmacology, 83(1), 42-50 (2012-10-05)
G protein-coupled receptor (GPCR) signaling is modulated by endocytosis and endosomal sorting of receptors between degradation and recycling. Differential regulation of these processes by endogenous ligands and synthetic drugs is a poorly understood area of GPCR signaling. Here, we describe
João Paulo Capela et al.
Neurotoxicology, 34, 254-263 (2012-09-18)
3,4-Methylenedioxymethamphetamine (MDMA or "Ecstasy") and 2,5-dimethoxy-4-iodoamphetamine hydrochloride (DOI) are hallucinogenic amphetamines with addictive properties. The hippocampus is involved in learning and memory and seems particularly vulnerable to amphetamine's neurotoxicity. We evaluated the neurotoxicity of DOI and MDMA in primary neuronal
[125I]-2-(2,5-Dimethoxy-4-iodophenyl)aminoethane ([125I]-2C-I) as a label for the 5-HT2 receptor in rat frontal cortex.
Johnson, et al.
Pharmacology, Biochemistry, and Behavior, 35, 211-211 (1989)
M I Zaĭchenko et al.
Zhurnal vysshei nervnoi deiatelnosti imeni I P Pavlova, 63(2), 246-255 (2013-07-23)
The influence of drugs, agonist (DOI) and antagonist (ketanserin) ofserotonin receptors 5-HT2 on the behavior of rats tested by the method of choice to the value of reinforcement was investigated. Depending on their preferences in food reinforcement rats were divided
Clint E Canal et al.
Drug testing and analysis, 4(7-8), 556-576 (2012-04-21)
Two primary animal models persist for assessing hallucinogenic potential of novel compounds and for examining the pharmacological and neurobiological substrates underlying the actions of classical hallucinogens, the two-lever drug discrimination procedure and the drug-induced head-twitch response (HTR) in rodents. The
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