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Merck

D153

(R)(−)-DOI hydrochloride

≥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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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

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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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000481910
0000481911
0000481910
0000481911
0000424555

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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
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
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