D153

(R)(−)-DOI hydrochloride

Name: (R)(−)-DOI hydrochloride
Brand: SIGMA

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

Synonym(s):

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

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All Photos(2)

About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₆INO₂ · HCl

CAS Number:

82864-02-6

Molecular Weight:

357.62

UNSPSC Code:

12352200

PubChem Substance ID:

24278404

NACRES:

NA.77

MDL number:

MFCD00153796

Product Name

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

SMILES string

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

InChI key

QVFDMWGKHUFODK-OGFXRTJISA-N

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

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

Quality Level

100

Gene Information

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

color

white

solubility

H₂O: ≥20 mg/mL
ethanol: soluble

Related Categories

Bioactive Small Molecule Agonists

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.

Storage Class

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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Pimavanserin, a 5-HT2A receptor inverse agonist, reverses psychosis-like behaviors in a rodent model of Alzheimer's disease.

Diana L Price et al.

Behavioural pharmacology, 23(4), 426-433 (2012-07-04)

Alzheimer's disease (AD) is a neurodegenerative disorder characterized by a progressive deterioration in cognitive functioning. Overall, 25-50% of patients with AD also show symptoms of psychosis including hallucinations and delusions. As all available antipsychotic drugs have a 'black-box' warning for

[Implication of 5-HT2A receptors in the genetic mechanisms of the brain 5-HT system autoregulation].

V S Naumenko et al.

Molekuliarnaia biologiia, 46(3), 416-422 (2012-08-15)

Brain serotonin (5-HT) system has been implicated in pathophysiology of anxiety, depression, drug addiction, and schizophrenia. 5-HT2A receptor is involved in the mechanisms of stress-induced psychopathology and impulsive behavior. Here, we investigated the role of 5-HT2A receptor in the autoregulation

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

[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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