| 词条 | 2,5-Dimethoxy-4-iodoamphetamine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477211688 | Name = DOI | IUPACName = 1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine | ImageFile = DOI2DACS.svg | ImageSize = 130px | ImageFile1 = DOI3Dan.gif | ImageSize1 = 150px |Section1={{Chembox Identifiers | IUPHAR_ligand = 147 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 1192 | PubChem = 1229 | 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 | InChIKey = BGMZUEKZENQUJY-UHFFFAOYAA | SMILES = IC(C=C1OC)=C(OC)C=C1CC(C)N | SMILES1 = IC(C=C1OC)=C(OC)C=C1C[C@@H](C)N | SMILES2 = IC(C=C1OC)=C(OC)C=C1C[C@H](C)N | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 6616 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BGMZUEKZENQUJY-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 42203-78-1 | CASNo2_Ref = {{cascite|changed|??}} | CASNo2 = 82864-06-0 | CASNo2_Comment = (R) | CASNo3_Ref = {{cascite|changed|??}} | CASNo3 = 99665-04-0 | CASNo3_Comment = (S) | CASNo4_Ref = {{cascite|changed|??}} | CASNo4 = 82864-02-6 | CASNo4_Comment = HCl |Section2={{Chembox Properties | Formula = C11H16INO2 | MolarMass = 321.1558 g/mol | MeltingPtC = 201.5 | MeltingPt_notes = (hydrochloride) | Solubility = 10 mg/mL[1] }}2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike many other substituted amphetamines, however, it is not primarily 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] While rare, 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] ResearchResearch[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
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] HistoryDOI 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 three 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] Legal statusAustraliaThe Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP) of Australia does not list DOI as a prohibited substance.[10] CanadaListed as a Schedule 1[11] as it is an analogue of amphetamine.[12] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.[13] DenmarkIllegal since 8 April 2007.[14] SwedenSveriges 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.[15]United StatesDOI is not scheduled in the United States,[16] 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|date=August 2015}} Scheduling DOI could cause problems for medical researchers. {{Citation needed|date=August 2015}} US State of FloridaDOI is a Schedule I controlled substance in the state of Florida.[17] See also
References1. ^{{cite web |url=http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/D101 |title=D101 DOI hydrochloride ≥98% (HPLC), solid |website=| accessdate= 13 April 2008 }} 2. ^1 2 {{cite book|author1=Shulgin, A |author2=Shulgin, A |chapter=#67 DOI|title=PiHKAL: A Chemical Love Story|publisher=Transform Press|isbn=978-0963009609|date=1990|archiveurl=https://www.erowid.org/library/books_online/pihkal/pihkal.shtml|archivedate=2009|chapter-url=https://www.erowid.org/library/books_online/pihkal/pihkal067.shtml}} 3. ^{{cite journal|author=DEA|date=June 2008|title=DEA Mircrogram|publisher=DEA, United States Government|url=http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0608/mg0608.html|accessdate=12 February 2009|archiveurl=https://web.archive.org/web/20090204025435/http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0608/mg0608.html|archivedate=2009-02-04|deadurl=yes|journal=|df=}} 4. ^{{cite web|url=http://www.eurekalert.org/pub_releases/2015-02/lsuh-lhn020915.php|title=LSU Health New Orleans research finds psychedelic drug prevents asthma development in mice|author=|date=|website=EurekAlert!}} 5. ^1 2 {{cite web|title=PDSP Ki Database |work=Psychoactive Drug Screening Program (PDSP) |author1=Roth, BL |author2=Driscol, J |url=http://pdsp.med.unc.edu/pdsp.php |publisher=University of North Carolina at Chapel Hill and the United States National Institute of Mental Health |accessdate=4 March 2014 |date=12 January 2011 |deadurl=yes |archiveurl=https://web.archive.org/web/20131108013656/http://pdsp.med.unc.edu/pdsp.php |archivedate=8 November 2013 |df= }} 6. ^1 {{cite journal|last=Canal|first=CE|author2=Morgan, D|title=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|journal=Drug Testing and Analysis|date=July 2012|volume=4|issue=7–8|pages=556–576|doi=10.1002/dta.1333|pmid=22517680|pmc=3722587}} 7. ^{{Cite journal |last=Yu |first=B |last2=Becnel |first2=J|last3=Zerfaoui |first3=M |last4=Rohatgi |first4=R |last5=Boulares |first5=AH |last6=Nichols |first6=CD|title=Serotonin 5-Hydroxytryptamine2A Receptor Activation Suppresses Tumor Necrosis Factor-α-Induced Inflammation with Extraordinary Potency |journal=Journal of Pharmacology and Experimental Therapeutics |year=2008 |volume=327 |issue=2 |pages=316–323 |doi=10.1124/jpet.108.143461 |pmid=18708586 }} 8. ^{{Cite journal |title=Rapid modulation of spine morphology by the 5-HT2A serotonin receptor through kalirin-7 signaling. |journal=Journal of Pharmacology and Experimental Therapeutics | date = 17 November 2009 |doi=10.1073/pnas.0905884106 |pmid=19889983|volume=106 |issue=46 |pmc=2780750 |pages=19575–80 | last1 = Jones | first1 = KA | last2 = Srivastava | first2 = DP | last3 = Allen | first3 = JA | last4 = Strachan | first4 = RT | last5 = Roth | first5 = BL | last6 = Penzes | first6 = P}} 9. ^{{Cite news |url=http://news.bbc.co.uk/1/hi/england/beds/bucks/herts/6308895.stm |title=New drug alert as three taken ill |publisher=BBC News |date=29 January 2007}} 10. ^{{cite web |title=POISONS STANDARD 2013 |department=Therapeutic Goods Administration |publisher=Australian Government Department of Health and Ageing |date=22 July 2013 |access-date=4 March 2014 |url=http://www.comlaw.gov.au/Details/F2013L01607/229bdf2e-7014-4379-b751-0b584f55d699 |format=PDF |author=Gill, A}} 11. ^ {{en icon}} 12. ^ {{en icon}} 13. ^[https://web.archive.org/web/20121018122345/http://www.justice.gc.ca/eng/news-nouv/nr-cp/2012/doc_32759.html] {{en icon}} 14. ^ {{en icon}} 15. ^http://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf 16. ^{{cite web|url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm|title=PART 1308 - Section 1308.11 Schedule I|author=|date=|website=www.deadiversion.usdoj.gov}} 17. ^{{cite web|url=http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html|title=Statutes & Constitution :View Statutes : Online Sunshine|author=|date=|website=leg.state.fl.us}} External links
6 : Substituted amphetamines|Iodoarenes|Phenol ethers|Designer drugs|Serotonin receptor agonists|TNF inhibitors |
||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 随便看 |
|
开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。