2,5-Dimethoxy-4-iodoamphetamine

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DOI
DOI2DACS.svg
DOI3Dan.gif
Names
IUPAC name
1-(4-Iodo-2,5-dimethoxyphenyl)-2-propanamine
Identifiers
42203-78-1 N
82864-06-0 (R) N
99665-04-0 (S) N
82864-02-6 HCl N
ChEMBL ChEMBL6616 YesY
ChemSpider 1192 YesY
147
Jmol 3D model Interactive image
Interactive image
Interactive image
PubChem 1229
  • InChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 YesY
    Key: BGMZUEKZENQUJY-UHFFFAOYSA-N YesY
  • InChI=1/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
    Key: BGMZUEKZENQUJY-UHFFFAOYAA
  • IC(C=C1OC)=C(OC)C=C1CC(C)N
  • IC(C=C1OC)=C(OC)C=C1C[C@@H](C)N
  • IC(C=C1OC)=C(OC)C=C1C[C@H](C)N
Properties
C11H16INO2
Molar mass 321.1558 g/mol
Melting point 201.5 °C (394.7 °F; 474.6 K) (hydrochloride)
10 mg/mL[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike other substituted amphetamines, however, it is not a stimulant.[2] DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer. In neuroscience research, [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of 5-HT2A serotonin receptors. DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience. The after effects include residual stimulation and difficulty sleeping, which, depending on the dose, may persist for days.[2] It is sometimes sold as a substitute for LSD, or even sold falsely as LSD, which may be dangerous because DOI does not have the same established safety profile as LSD.[3]

Research

Research[4] suggests that administration of (R)-DOI blocks pulmonary inflammation, mucus hyper-production, airway hyper-responsiveness and turns off key genes in in-lung immune response. These effects block the development of allergic asthma in a mouse model.

Pharmacology

Binding Profile of DOI and its isomers
Receptor Ki (racemic DOI)[5] Ki (R-DOI)[5] Ki (S-DOI)[5] Intrinsic activity[6]
5-HT1A 2355 nM 3843 nM ND ND
5-HT1B 1261 nM ND ND ND
5-HT1D 1241.3 nM ND ND ND
5-HT1E 2970 nM ND ND ND
5-HT1F 2125.44 nM ND ND ND
5-HT2A 0.68 nM 0.65 nM 0.65 nM Partial agonist.
5-HT2B 20.03 nM 53.70318 nM 28.183829 nM Partial agonist/full agonist
5-HT2C 2.38 nM 5.370318 nM 8.317638 nM Full agonist when coupled to phospholipase A. Partial agonist (intrinsic efficacy = 53%), when coupled to phospholipase C.
5-HT5A 1000 nM ND ND ND
5-HT5A 1000 nM ND ND ND
5-HT6 >10000 nM ND ND ND


DOI is a 5-HT2A, 5-HT2B and 5-HT2C receptor agonist.[6]

DOI has been shown to be an extremely potent inhibitor of tumour necrosis factor-alpha inflammation at picomolar concentrations in cell studies. TNF-alpha is an important target for research into degenerative conditions such as rheumatoid arthritis and Alzheimer's disease, where the disease process involves tissue damage through chronic inflammation. This could make DOI and other 5-HT2A agonists an entirely new area for development of novel treatments for these conditions.[7]

DOI has also been shown to induce rapid growth and reorganization of dendritic spines and synaptic connections with other neurons, processes known to underlie neuroplasticity.[8]

History

DOI was first synthesized by Alexander Shulgin.[2] The radioactive iodine-125 form of DOI for PET imaging was first developed in the lab of David E. Nichols.

In January 2007, British Police reported that 3 young men had fallen ill, reportedly, after taking DOI at a rave in Biggleswade, near Milton Keynes, and warned others who had taken it to seek medical attention. This would appear to be the first indication that DOI has found more widespread use as a recreational drug in the UK.[9]

An extremely large increase of the hallucinogenic drug has been seen in sales in Adelaide, Australia. It is commonly sold as LSD or just "trips".[10]

Legal Status

Australia

The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP) of Australia does not list DOI as a prohibited substance.[11]

Canada

Listed as a Schedule 1[12] as it is an analogue of amphetamine.[13] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.[14]

Denmark

Illegal since 8 April 2007.[15]

Sweden

Sveriges riksdag added DOI to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of August 30, 2007, published by Medical Products Agency in their regulation LVFS 2007:10 listed as DOI, 4-jod-2,5-dimetoxi-amfetamin.[16]

United States

DOI is not scheduled in the United States,[17] but it is likely that DOI would be considered an analog (of DOB), in which case, sales or possession could be prosecuted under the Federal Analogue Act. DOI is regularly used in animal and in vitro research.[citation needed] Scheduling DOI could cause problems for medical researchers.[citation needed]

US State of Florida

DOI is a Schedule I controlled substance in the state of Florida.[18]

See also

References

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  4. http://www.eurekalert.org/pub_releases/2015-02/lsuh-lhn020915.php
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  12. [1] (English)
  13. [2] (English)
  14. [3] (English)
  15. http://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf
  16. §1308.11 Schedule I.
  17. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

External links