D153

(R)(−)-DOI hydrochloride

Name: (R)(&#8722;)-DOI hydrochloride
Brand: SIGMA

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

Sinonimo/i:

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

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Informazioni su questo articolo

Formula empirica (notazione di Hill):

C₁₁H₁₆INO₂ · HCl

Numero CAS:

82864-02-6

Peso molecolare:

357.62

UNSPSC Code:

12352200

PubChem Substance ID:

24278404

NACRES:

NA.77

MDL number:

MFCD00153796

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Nome del prodotto

(R)(−)-DOI hydrochloride, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

optical activity

[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, kontrollierte Droge in Deutschland

color

white

solubility

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

InChI key

QVFDMWGKHUFODK-OGFXRTJISA-N

Gene Information

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

Categorie correlate

Bioactive Small Molecules

Biochem/physiol Actions

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

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.

Classe di stoccaggio

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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I documenti relativi ai prodotti acquistati recentemente sono disponibili nell’Archivio dei documenti.

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The neurotoxicity of hallucinogenic amphetamines in primary cultures of hippocampal neurons.

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)

Functional selectivity in serotonin receptor 2A (5-HT2A) endocytosis, recycling, and phosphorylation.

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

[Effect of agonists and antagonists of 5-HT2 receptors on rats with different choice of reinforcement value].

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

DOI-induced deficits in prepulse inhibition in Wistar rats are reversed by mGlu2/3 receptor stimulation.

Lena Wischhof et al.

Pharmacology, biochemistry, and behavior, 102(1), 6-12 (2012-04-04)

Prepulse inhibition (PPI) of the acoustic startle response (ASR) provides a measure of sensorimotor gating mechanisms that are impaired in schizophrenia patients. Interactions of the serotonin (5-hydroxytryptamine, 5-HT) and glutamatergic systems, especially via the 5-HT(2A) receptor subtype, have been implicated

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