2,5-Dimethoxy-4-iodoamphetamine

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DOI
DOI2DACS.svg
DOI3Dan.gif
Names
IUPAC name
1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine
Identifiers
42203-78-1 N
82864-06-0 (R) N
99665-04-0 (S) N
82864-02-6 HCl N
3D model (Jmol) Interactive image
Interactive image
Interactive image
ChEMBL ChEMBL6616 YesY
ChemSpider 1192 YesY
ECHA InfoCard 100.164.735
147
PubChem 1229
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[edit]

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[edit]

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[edit]

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 in DOI sales has been seen in Adelaide, Australia as of 2009. It is commonly sold as LSD or just "trips".[10]

Legal Status[edit]

Australia[edit]

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

Canada[edit]

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[edit]

Illegal since 8 April 2007.[15]

Sweden[edit]

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[edit]

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 occasionally used in animal and in vitro research.[citation needed] Scheduling DOI could cause problems for medical researchers.[citation needed]

US State of Florida[edit]

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

See also[edit]

References[edit]

  1. ^ "D101 DOI hydrochloride ≥98% (HPLC), solid". Retrieved 13 April 2008. 
  2. ^ a b c Shulgin, A; Shulgin, A (1990). "#67 DOI". PiHKAL: A Chemical Love Story. Transform Press. ISBN 978-0963009609. Archived from the original on 2009. 
  3. ^ DEA (June 2008). "DEA Mircrogram". DEA, United States Government. Archived from the original on 4 February 2009. Retrieved 12 February 2009. 
  4. ^ http://www.eurekalert.org/pub_releases/2015-02/lsuh-lhn020915.php
  5. ^ a b c Roth, BL; Driscol, J (12 January 2011). "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Archived from the original on 8 November 2013. Retrieved 4 March 2014. 
  6. ^ a b Canal, CE; Morgan, D (July 2012). "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" (PDF). Drug Testing and Analysis. 4 (7-8): 556–576. doi:10.1002/dta.1333. PMC 3722587Freely accessible. PMID 22517680. 
  7. ^ Yu, B; Becnel, J; Zerfaoui, M; Rohatgi, R; Boulares, AH; Nichols, CD (2008). "Serotonin 5-Hydroxytryptamine2A Receptor Activation Suppresses Tumor Necrosis Factor-α-Induced Inflammation with Extraordinary Potency". Journal of Pharmacology and Experimental Therapeutics. 327 (2): 316–323. doi:10.1124/jpet.108.143461. PMID 18708586. 
  8. ^ Jones, KA; Srivastava, DP; Allen, JA; Strachan, RT; Roth, BL; Penzes, P (17 November 2009). "Rapid modulation of spine morphology by the 5-HT2A serotonin receptor through kalirin-7 signaling.". Journal of Pharmacology and Experimental Therapeutics. 106: 19575–80. doi:10.1073/pnas.0905884106. PMC 2780750Freely accessible. PMID 19889983. 
  9. ^ "New drug alert as three taken ill". BBC News. 29 January 2007. 
  10. ^ "Extra-strong new LSD-type hallucinogenic drug hits Adelaide, police warn". Adelaide Now. October 2, 2009. 
  11. ^ Gill, A (22 July 2013). "POISONS STANDARD 2013" (PDF). Therapeutic Goods Administration. Australian Government Department of Health and Ageing. Retrieved 4 March 2014. 
  12. ^ [1] (English)
  13. ^ [2] (English)
  14. ^ [3][permanent dead link] (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[edit]

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