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Revision as of 17:07, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 447434284 of page 2,5-Dimethoxy-4-ethylamphetamine for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 18:12, 29 November 2023 edit Kimen8 (talk | contribs)Extended confirmed users5,112 edits Changing short description from "Chemical compound" to "Psychedelic drug"Tag: Shortdesc helper 
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{{Short description|Psychedelic drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Redirect|DOET|the book|The Design of Everyday Things}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 443312632
| Watchedfields = changed
| IUPAC_name = 1-(4-ethyl-2,5-dimethoxy-phenyl)propan-2-amine
| verifiedrevid = 477211641
| image = 2,5-Dimethoxy-4-ethylamphetamine.svg
| IUPAC_name = 1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine
| width = 230px
| image = 2,5-Dimethoxy-4-ethylamphetamine.svg
| width = 230px


<!--Clinical data--> <!--Clinical data-->| tradename =
| tradename = | pregnancy_category =
| legal_AU = Schedule 9
| pregnancy_category =
| legal_BR = F2
| legal_status = Schedule I
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=] |language=pt-BR |publication-date=2023-07-25}}</ref>
| routes_of_administration =
| legal_CA = Schedule I
| legal_DE = Anlage I
| legal_UN = P I
| legal_US = Schedule I
| legal_UK = Class A
| routes_of_administration = <!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion = <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|cas}}
| CAS_number = 22004-32-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9SK6K682UL
| ATC_prefix =
| ATC_suffix =
| PubChem = 27402
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01467
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25499
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 8224
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22714


<!--Pharmacokinetic data--> <!--Chemical data-->| C = 13
| H = 21
| bioavailability =
| N = 1
| protein_bound =
| O = 2
| metabolism =
| smiles = O(c1cc(c(OC)cc1CC(N)C)CC)C
| elimination_half-life =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion =
| StdInChI = 1S/C13H21NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h7-9H,5-6,14H2,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HXJKWPGVENNMCC-UHFFFAOYSA-N
| synonyms = 2,5-dimethoxy-4-ethylamphetamine
}}


'''2,5-Dimethoxy-4-ethylamphetamine''' ('''DOET''', '''DOE''', '''Hecate''') is a ] ] of the ] and ] ]es. It was first ] by ], and was described in his book '']'' (''Phenethylamines i Have Known And Loved'').<ref name="PiHKAL">{{cite book |url=https://erowid.org/library/books_online/pihkal/pihkal066.shtml |title=PiHKAL: A Chemical Love Story |vauthors=Shulgin A, Shulgin A |date=September 1991 |publisher=Transform Press |isbn=0-9630096-0-5 |location=United States |pages=978}}</ref>
<!--Identifiers-->
| CAS_number = <!-- blanked - oldvalue: 15588-95-1 -->
| ATC_prefix =
| ATC_suffix =
| PubChem = 27402
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01467
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25499
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 8224


== Chemistry ==
<!--Chemical data-->
DOET is in a class of compounds commonly known as ]s; its full chemical name is 4-ethyl-2,5-dimethoxy-alpha-methylbenzeneethanamine, or 1-(2,5-dimethoxy-4-ethylphenyl)propan-2-amine. It has an active ] and (R)-DOET is the more active enantiomer. DOET is an extremely rare compound and reports of its effects and toxicology in humans are sparse. However, like the more common 2,5-dimethoxy-amphetamine analogues ], ] and ], it is a potent and long-acting psychedelic. Removal of the alpha-methyl moiety yields the 2-carbon analogue, commonly known as ], another psychedelic compound first synthesized by Dr. ].
| chemical_formula = C<sub>13</sub>H<sub>21</sub>NO<sub>2</sub>


== Pharmacology ==
| molecular_weight = 223.31
Similarly to related drugs like ], DOET likely acts as a ], ], and ] ] ].{{citation needed|date=January 2013}} It is an agonist of human ].<ref>{{cite journal | vauthors = Lewin AH, Miller GM, Gilmour B | title = Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class | journal = Bioorganic & Medicinal Chemistry | volume = 19 | issue = 23 | pages = 7044–7048 | date = December 2011 | pmid = 22037049 | pmc = 3236098 | doi = 10.1016/j.bmc.2011.10.007 }}</ref><ref>{{cite web|title=Compound ID: CHEMBL2360469|url=https://www.ebi.ac.uk/chembl/compound/inspect/CHEMBL2360469|work=ChEMBL|access-date=29 April 2014}}</ref>
| smiles = O(c1cc(c(OC)cc1CC(N)C)CC)C

| InChI = 1/C13H21NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h7-9H,5-6,14H2,1-4H3
== Effects ==
| InChIKey = HXJKWPGVENNMCC-UHFFFAOYAW
DOET produces psychedelic effects that last up 14–20 hours. In PiHKAL, Shulgin lists the dosage of DOET as being 2–7&nbsp;mg orally, with 6–7&nbsp;mg being the dosage for full, desired effects.<ref name="PiHKAL"/>
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C13H21NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h7-9H,5-6,14H2,1-4H3
==Legal status==
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
Internationally, DOET is a Schedule I controlled drug; under the ], it's legal only for medical uses or scientific research:.
| StdInChIKey = HXJKWPGVENNMCC-UHFFFAOYSA-N

| synonyms = 2,5-dimethoxy-4-ethylamphetamine
===United States===
}}
DOET is classified as a ] substance in the United States and is similarly controlled in other parts of the world.

===Australia===
DOET is considered a Schedule 9 prohibited substance in Australia under the ] (October 2015).<ref name="Poisons Standard">{{cite web | title = Poisons Standard | date = October 2015 | url = https://www.comlaw.gov.au/Details/F2015L01534 | work = Therapeutics Goods Administration | publisher = Australian Government }}</ref> 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.<ref name="Poisons Standard" />

== See also ==
* ]s

== References ==
{{Reflist}}

== External links ==
*
*

{{Hallucinogens}}
{{Phenethylamines}}
{{Serotonergics}}
{{TAAR ligands}}

{{DEFAULTSORT:Dimethoxy-4-ethylamphetamine, 2,5-}}
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