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D153

Sigma-Aldrich

(R)(−)-DOI hydrochloride

≥98% (HPLC), 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
MDL number:
MFCD00153796
UNSPSC Code:
12352200
PubChem Substance ID:
24278404
NACRES:
NA.77

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

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)

Biochem/physiol Actions

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
[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)
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