DOI hydrochloride

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Description: 5-HT2A and 5-HT2C agonist
Alternative Names: (±)-2,5-Dimethoxy-4-iodoamphetamine hydrochloride
Chemical Name: 4-Iodo-2,5-dimethoxy-α-methylbenzeneethanamine hydrochloride
Purity: ≥98% (HPLC)
Citations (4)
Reviews (2)
Literature (3)

Biological Activity for DOI hydrochloride

DOI hydrochloride is a brain penetrant, mixed 5-HT2A/5-HT2C receptor agonist (Ki values are 0.7, 2.4 and 20 nM for 5-HT2A, 5-HT2C and 5-HT2B receptors respectively). Reduces rapid eye movement (REM) and slow wave sleep and increases waking in the rat. Hallucinogenic agent. Acts via 5-HT2A receptors to inhibit the inflammatory effects of tumor necrosis factor (TNF)-α.

Technical Data for DOI hydrochloride

M. Wt 357.62
Formula C11H16INO2.HCl
Storage Store at RT
Purity ≥98% (HPLC)
CAS Number 42203-78-1
PubChem ID 170617
Smiles IC1=C(OC)C=C(CC(C)N)C(OC)=C1.Cl

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for DOI hydrochloride

Solvent Max Conc. mg/mL Max Conc. mM
water 17.88 50

Preparing Stock Solutions for DOI hydrochloride

The following data is based on the product molecular weight 357.62. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 5.59 mL 27.96 mL 55.93 mL
2.5 mM 1.12 mL 5.59 mL 11.19 mL
5 mM 0.56 mL 2.8 mL 5.59 mL
25 mM 0.11 mL 0.56 mL 1.12 mL

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Product Datasheets for DOI hydrochloride

Certificate of Analysis / Product Datasheet
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References for DOI hydrochloride

References are publications that support the biological activity of the product.

Monti and Jantos (2006) Effects of serotonin 5-HT2A/2C receptor agonist DOI and of the selective 5-HT2A or 5-HT2C receptor antagonists EMD 281014 and SB-243213 respectively, on sleep and waking in the rat. Eur.J.Pharmacol. 553 163 PMID: 17059817

Yu et al (2008) Serotonin 5-hydroxytryptamine2A receptor activation suppresses tumor necrosis factor-α-induced inflammation with extraordinary potency. J.Pharmacol.Exp.Ther. 327 316 PMID: 18708586

Nelson et al (1999) Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. Naunyn-Schmied.Arch.Pharmacol. 359 1

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Keywords: DOI hydrochloride, DOI hydrochloride supplier, Mixed, 5-H2A, 5-HT2C, agonists, serotonin, receptors, 5-hydroxytryptamine, (±)-2,5-Dimethoxy-4-iodoamphetamine, hydrochloride, 5-HT2A, Receptors, 2643, Tocris Bioscience

4 Citations for DOI hydrochloride

Citations are publications that use Tocris products. Selected citations for DOI hydrochloride include:

Goda et al (2013) Serotonergic hallucinogens differentially modify gamma and high frequency oscillations in the rat nucleus accumbens. Psychopharmacology (Berl) 228 271 PMID: 23525524

Medrihan et al (2017) Initiation of Behavioral Response to Antidepressants by Cholecystokinin Neurons of the Dentate Gyrus. Neuron 95 564 PMID: 28735749

Moutkine et al (2017) Heterodimers of serotonin receptor subtypes 2 are driven by 5-HT2C protomers. J Biol Chem 292 6352 PMID: 28258217

Wood et al (2011) Serotonin, via HTR2 receptors, excites neurons in a cortical-like premotor nucleus necessary for song learning and production. J Neurosci 31 13808 PMID: 21957243

Do you know of a great paper that uses DOI hydrochloride from Tocris? Please let us know.

Reviews for DOI hydrochloride

Average Rating: 5 (Based on 2 Reviews.)

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Antidepressantsby Cholecystokinin Neurons of the Dentate Gyrus.
By Anonymous on 02/03/2020
Assay Type: In Vivo
Species: Mouse

20mM DOI hydrochloride

PMID: 28735749
review image

Superb Experiments Regarding Possibility of Visual/Tactile/Auditory Hallucinatory Effects in Non-Human Animals.
By Anonymous on 08/17/2017
Assay Type: In Vivo
Species: Mouse

I received the product promptly, which is satisfactory in and of itself. In addition, the DOI HCl (>98%) was both pure, and in a form that was convenient for measurement and application. The product was used to determine if non-human animals (in this case, the common mouse) are also capable of receiving hallucinatory/pseud-hallucinatory effects comparable to humans. Tests were based around testing for cognitive, visual, tactile, aural, and gustatory alterations, as well as altered behavioral patterns, not observed in the control group. Tests performed featured experiments (held against behavior of control group) such as: Determining if application of DOI (through careful dissolution in water source) caused altered preference and/or reaction to simulated threats (such as models or pictured of predators), preference regarding food (test group tended to avoid sweet food after consumption during the duration of effects), increase or decrease in sexual behavior (test group showed increased sexual behavior, such as receptivity to intercourse for females and increased mating attempts in males, but decreased competitive/territorial responses to other males), differences in response to auditory cues versus control group (differences noted, but more research required), changes in ability with regards to simple problem-solving versus control (test group showed increased interest and attentiveness to cognitive and sensory stimuli, heightened speed, efficiency, and reflexivity regarding solving simple problems, but agitation or confusion regarding tests involving colors, shapes, sounds, and navigation/stability). Results were promising, but remain inconclusive until more testing and experimentation can be administered. Overall, your product was very satisfactory, and I will certainly continue using your services when needed, and I am more than happy to recommend your services to my colleagues, as well as other biological scientists.

Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.

5-HT Receptors Scientific Review

5-HT Receptors Scientific Review

Written by Nicholas M. Barnes and John F. Neumaier, this review summarizes the various serotonin receptor subtypes and their importance in mediating the role of serotonin in numerous physiological and pharmacological processes. Compounds available from Tocris are listed.

Depression Poster

Depression Poster

Major depressive disorder is characterized by depressed mood and a loss of interest and/or pleasure. Updated in 2015 this poster highlights presynaptic and postsynaptic targets for the potential treatment of major depressive disorder, as well as outlining the pharmacology of currently approved antidepressant drugs.

Parkinson's Disease Poster

Parkinson's Disease Poster

Parkinson's disease (PD) causes chronic disability and is the second most common neurodegenerative condition. This poster outlines the neurobiology of the disease, as well as highlighting current therapeutic treatments for symptomatic PD, and emerging therapeutic strategies to delay PD onset and progression.