| 词条 | 2,5-Dimethoxy-4-bromoamphetamine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477192160 | ImageFile1 = DOB-racemic-skeletal.svg | ImageName1 = Chemical structure of (±)-DOB | ImageFile2 = DOB-3d-sticks.png | ImageCaption2 = (R)-isomer | IUPACName = 1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-amine | OtherNames = 4-Bromo-2,5-dimethoxy-amphetamine |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 55902 | InChI = 1/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 | InChIKey = FXMWUTGUCAKGQL-UHFFFAOYAD | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 6607 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C11H16BrNO2/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 = FXMWUTGUCAKGQL-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 64638-07-9 | CASNo_Comment = (racemate) | CASNo1_Ref = {{cascite|changed|??}} | CASNo1 = 43061-15-0 | CASNo1_Comment = (R) | CASNo2_Ref = {{cascite|changed|??}} | CASNo2 = 43061-16-1 | CASNo2_Comment = (S) | PubChem = 62065 | IUPHAR_ligand = 155 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01484 | SMILES = Brc1cc(OC)c(cc1OC)CC(N)C }} |Section2={{Chembox Properties | Formula = C11H16BrNO2 | MolarMass = 274.15 g/mol | Appearance = | Density = | MeltingPtC = 63 to 65 | MeltingPt_notes = (207–208 °C hydrochloride) | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN)[1] and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967.[2][3] Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story. ChemistryThe full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has a stereocenter and R-(–)-DOB is the eutomer. This is an important finding as it is suggestive that it is targeting different receptors relative to most other phenethylamines (e.g. MDMA) where the R-isomer serves as the distomer. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction of the extremities. DOB is one of the most potent compounds in PiHKAL; while the active dose is similar to that of DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors,[4] making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action. Omission of the amphetamine related α-methyl leads to 2C-B, a compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist which results in drastically reduced vasoconstriction.{{Citation needed|date=December 2017}} PharmacologyDOB is a 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist.[5] Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily. It is an agonist of human TAAR1.[6] It has been suggested that DOB is a prodrug metabolized in the lungs.[2][7] Legal statusInternationally DOB is a Schedule I drug under the Convention on Psychotropic Substances.[8] CanadaListed as a Schedule 1 as it is an analogue of amphetamine.[9] AustraliaDOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).[10] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[10] RussiaSchedule I, possession of at least 10mg is a criminal offence.[11] See also
References1. ^{{cite book|author=World Health Organization|title=International Nonproprietary Names (INN) for Pharmaceutical Substances|url=https://books.google.com/books?id=HcogPwAACAAJ|year=2000|publisher=World Health Organization|isbn=978-0-11-986227-0}} 2. ^1 Erowid Online Books: "PiHKAL" - #62 DOB 3. ^{{cite journal |doi=10.1159/000136181 |pmid=5570923|title=4-Bromo-2,5-Dimethoxyphenylisopropylamine, a New Centrally Active Amphetamine Analog|journal=Pharmacology|volume=5|issue=2|pages=103–107|year=1971|last1=Shulgin|first1=A.T.|last2=Sargent|first2=T.|last3=Naranjo|first3=C.}} 4. ^{{Cite journal|last=Parrish|first=Jason C.|last2=Braden|first2=Michael R.|last3=Gundy|first3=Emily|last4=Nichols|first4=David E.|date=2005-12-01|title=Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists|journal=Journal of Neurochemistry|language=en|volume=95|issue=6|pages=1575–1584|doi=10.1111/j.1471-4159.2005.03477.x|pmid=16277614|issn=1471-4159}} 5. ^{{Cite journal | doi = 10.1371/journal.pone.0009019| pmid = 20126400| pmc = 2814854| title = Psychedelics and the Human Receptorome| journal = PLoS ONE| volume = 5| issue = 2| pages = e9019| year = 2010| last1 = Ray | first1 = T. S. }} 6. ^{{cite web|title=Articleid 50034244 |url=http://www.bindingdb.org/jsp/dbsearch/PrimarySearch_pubmed.jsp?pubmed=50034244&pubmed_submit=TBD|work=Binding Database|accessdate=29 April 2014}} 7. ^{{cite web|url=http://www.cognitiveliberty.org/shulgin/blg/2005/05/dob-and-other-possible-prodrugs.html |title=Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs |accessdate=18 November 2009 |last=Shulgin |date=2005-05-03}} 8. ^{{cite web|url=http://www.incb.org/pdf/e/list/green.pdf |title=List of psychotropic substances under international control |accessdate=30 March 2007 |archiveurl=https://web.archive.org/web/20070302130637/http://www.incb.org/pdf/e/list/green.pdf |archivedate=2 March 2007 |deadurl=yes |df= }} 9. ^ {{en icon}} 10. ^1 Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534 11. ^http://base.garant.ru/70237124/ External links
6 : Serotonin receptor agonists|Substituted amphetamines|Bromoarenes|Phenol ethers|Designer drugs|TAAR1 agonists |
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