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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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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Pharmacological characterization of ear-scratch response in mice as a behavioral model for selective 5-HT2-receptor agonists and evidence for 5-HT1B- and 5-HT2-receptor interactions.

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

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

Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model.

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

Do functional relationships exist between 5-HT1A and 5-HT2 receptors?

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

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

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