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D153

Sigma-Aldrich

(R)(−)-DOI hydrochloride

≥98% (HPLC), solid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C11H16INO2 · HCl
Número de CAS:
82864-02-6
Peso molecular:
357.62
Número MDL:
MFCD00153796
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24278404
NACRES:
NA.77

Nivel de calidad

100

Análisis

≥98% (HPLC)

formulario

solid

actividad óptica

[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

color

white

solubilidad

H2O: ≥20 mg/mL
ethanol: soluble

cadena SMILES

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

Clave InChI

QVFDMWGKHUFODK-OGFXRTJISA-N

Información sobre el gen

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

Acciones bioquímicas o fisiológicas

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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N A Darmani et al.
Pharmacology, biochemistry, and behavior, 37(1), 95-99 (1990-09-01)
(+/-) 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane [(+/-)-DOI], a phenylisopropylamine hallucinogen, is a 5-HT2-receptor agonist. The drug induced a dose-dependent increase in ear-scratch response (ESR) in mice, and the R(-)-isomer was more than 6 times as potent as its S(+)-enantiomer. The induced behavior was potently
N A Darmani et al.
Pharmacology, biochemistry, and behavior, 36(4), 901-906 (1990-08-01)
To investigate the possible functional relationship between 5-HT1 and 5-HT2 receptors, we studied the effects of a nonselective 5-HT agonist (5-MeO DMT), a 5-HT1A-selective (8-OH-DPAT) and a 5-HT1B/5-HT1C-selective (TFMPP) agonist on the head-twitch behavior induced by the putative 5-HT2-selective receptor
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
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
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
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