Misplaced Pages

Diethyltryptamine: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 07:14, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 06:36, 17 November 2023 edit undoPashihiko (talk | contribs)Extended confirmed users3,552 editsNo edit summary 
(56 intermediate revisions by 41 users not shown)
Line 1: Line 1:
{{Short description|Chemical compound}}
{{drugbox | verifiedrevid = 414422677
{{disputed|date=October 2011}}
|
{{Drugbox
| IUPAC_name = ''N'',''N''-diethyl-2-(1''H''-indol-3-yl)ethanamine
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443637796
| IUPAC_name = ''N'',''N''-diethyl-2-(1''H''-indol-3-yl)ethan-2-amine
| image = Diethyltryptamine.svg | image = Diethyltryptamine.svg
| image2 = DET-3d-sticks.png
| width = 140 | width = 140
| image2 = DET-3d-sticks.png

<!--Clinical data-->
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_BR = F2
| 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>
| legal_CA = Schedule III
| legal_UK = Class A
| legal_US = Schedule I
| legal_DE = Anlage I
| legal_UN = P I
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 61-51-8
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 916E8V4S2V
| ATC_prefix = none
| ATC_suffix =
| PubChem = 6090
| KEGG = C22726
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01460
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5865 | ChemSpiderID = 5865
| InChI = 1/C14H20N2/c1-3-16(4-2)10-9-12-11-15-14-8-6-5-7-13(12)14/h5-8,11,15H,3-4,9-10H2,1-2H3
| InChIKey = LSSUMOWDTKZHHT-UHFFFAOYAY
| smiles1 = c1cccc2c1c(cn2)CCN(CC)CC
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 142936 | ChEMBL = 142936

<!--Chemical data-->
| C=14 | H=20 | N=2
| smiles = CCN(CC)CCC1=CNC2=C1C=CC=C2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H20N2/c1-3-16(4-2)10-9-12-11-15-14-8-6-5-7-13(12)14/h5-8,11,15H,3-4,9-10H2,1-2H3 | StdInChI = 1S/C14H20N2/c1-3-16(4-2)10-9-12-11-15-14-8-6-5-7-13(12)14/h5-8,11,15H,3-4,9-10H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LSSUMOWDTKZHHT-UHFFFAOYSA-N | StdInChIKey = LSSUMOWDTKZHHT-UHFFFAOYSA-N
| CAS_number = 7558-72-7
| ATC_prefix = none
| ATC_suffix =
| DrugBank = DB01460
| PubChem = 6090
| C=14 | H=20 | N=2
| molecular_weight = 216.32 g/mol
| smiles = CCN(CC)CCC1=CNC2=C1C=CC=C2
| melting_point = 169 | melting_point = 169
| melting_high = 171 | melting_high = 171
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK = Class A
| legal_US = Schedule I
| legal_status =
| routes_of_administration =
}} }}


'''DET''', also known under its chemical name '''''N'',''N''-diethyltryptamine''' and as '''T-9''',<ref name="titleErowid DET Vault : Chemistry">{{cite web |url=http://www.erowid.org/chemicals/det/det_chemistry.shtml |title=Erowid DET Vault : Chemistry |accessdate=2008-01-08 |work=}}</ref> is a ] closely related to ] and ]. However, despite its ] to DMT it is active orally around 50–100 ] without the aid of ] lasting about 2–4 hours. '''DET''', also known under its chemical name '''''N'',''N''-diethyltryptamine''' and as '''T-9''',<ref name="titleErowid DET Vault : Chemistry">{{cite web |url=http://www.erowid.org/chemicals/det/det_chemistry.shtml |title=Erowid DET Vault : Chemistry |access-date=2008-01-08 }}</ref> is a ] closely related to ] and ]. However, despite its ] to DMT, its activity is induced by an oral dose of around 50–100 ], without the aid of ], and the effects last for about 2–4 hours.


==Chemistry== ==Chemistry==
DET is an analogue of the common ] hallucinogen ] or DMT.

DET is an analogue of the common ] hallucinogen ] or DMT. DET is sometimes preferred over DMT because it can be taken orally whereas DMT cannot. This is because the enzyme ] degrades DMT into an inactive compound before it is absorbed. To overcome this, it must be administered in a different manner, i.e. intravenously, intramuscularly, by inhalation, by insufflation, or rectally. Because DET has ethyl groups attached to its nitrogen atom monoamine oxidase is unable to degrade it. This is true for many other tryptamines with larger nitrogen substitutents.


==Pharmacology== ==Pharmacology==
{{More citations needed|section|date=October 2013}}

The mechanism of action is thought to be ] ], much like other ].<ref>{{cite journal | vauthors = Winter JC | title = Behavioral effects of N,N-diethyltryptamine: absence of antagonism by xylamidine tosylate | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 169 | issue = 1 | pages = 7–16 | date = September 1969 | pmid = 5306645 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=5306645 }}</ref>


DET is sometimes preferred over DMT because it can be taken orally, whereas DMT cannot. This is because the enzyme ] degrades DMT into an inactive compound before it is absorbed. To overcome this, it must be administered in a different manner, i.e. intravenously, intramuscularly, by inhalation, by insufflation, rectally, or by ingestion along with an inhibitor of monoamine oxidase. Because DET has ethyl groups attached to its nitrogen atom, monoamine oxidase is unable to degrade it. This is also true for many other tryptamines with larger nitrogen substituents.
The mechanism of action is thought to be ] ], much like other ].<ref>{{cite journal |author=Winter JC |title=Behavioral effects of N,N-diethyltryptamine: absence of antagonism by xylamidine tosylate |journal=J. Pharmacol. Exp. Ther. |volume=169 |issue=1 |pages=7–16 |year=1969 |month=September |pmid=5306645 |doi= |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=5306645}}</ref>


==Biochemistry== ==Biochemistry==
Though DET is a ] compound with no known ] it has been used with ] of '']'' to produce the synthetic chemicals ] and ], as opposed the naturally occurring ] and ]. Isolation of the alkaloids resulted in 3.3% 4-HO-DET and 0.01-0.8% 4-PO-DET.<ref>{{cite journal |author=Gartz J |title=Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe |journal=J. Basic Microbiol. |volume=29 |issue=6 |pages=347–52 |year=1989 |pmid=2614674 |doi= 10.1002/jobm.3620290608|url=}}</ref> Although DET is a ] compound with no known ], it has been used in conjunction with the ] of '']'' to produce the synthetic chemicals ] and ], as opposed to the naturally occurring ] and ]. Isolation of the alkaloids resulted in 3.3% 4-HO-DET and 0.01-0.8% 4-PO-DET.<ref>{{cite journal | vauthors = Gartz J | title = Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe | journal = Journal of Basic Microbiology | volume = 29 | issue = 6 | pages = 347–52 | year = 1989 | pmid = 2614674 | doi = 10.1002/jobm.3620290608 | s2cid = 43308695 }}</ref>


==Psychosis model== ==Psychosis model==
Early studies of DET, as well as other psychedelics, mainly focused on the believed ] properties.<ref name="titlePSILOCYBIN AND DIETHYLTRYPTAMINE: Early studies of DET as well as other psychedelics were focused on their presumed ] properties.<ref name="titlePSILOCYBIN AND DIETHYLTRYPTAMINE:
TWO TRYPTAMINE HALLUCINOGENS">{{cite web |url=http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=2633 |title=PSILOCYBIN AND DIETHYLTRYPTAMINE: TWO TRYPTAMINE HALLUCINOGENS |accessdate=2008-01-03 |format= |work=}}</ref> Researchers theorized that abnormal ]s of endogenous chemicals such as ], ], and ] could be the explanation for ]s as ], or ].<ref name="title">{{cite web |url=http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=2360 |title=Effects of LSD-25, N,N-Dimethyltryptamine (DMT), and N,N-Diethyltryptamine (DET) on the Photic Evoked Responses in the unanesthetized Rabbit |accessdate=2008-01-03 |format= |work=}}</ref> With the progression of science and ] understanding this belief has been dismissed by most researchers. TWO TRYPTAMINE HALLUCINOGENS">{{cite journal | vauthors = Böszörmenyi Z | title = Psilocybin and diethyltryptamine: Two tryptamine hallucinogens. | journal = Neuro-psychopharm. | date = 1960 | volume = 2 | pages = 226–9 | url = http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=2633 }}</ref> Researchers theorized that abnormal ]s of endogenous chemicals such as ], ], and ] could be the explanation for ]s such as ], or ].<ref name="pmid5839429">{{cite journal | vauthors = Khazan N, McCash D | title = Effects of LSD-25, n,n-dimethyltryptamine (DMT), and N,N-diethyltryptamine (DET) on the photic evoked responses in the unanesthetized rabbit | journal = Archives Internationales de Pharmacodynamie et de Therapie | volume = 154 | issue = 2 | pages = 474–83 | date = April 1965 | pmid = 5839429 | url = http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=2360 }}</ref> With the progression of science and ] understanding, this belief has been dismissed by most researchers.


==See also== ==Legal status==
Internationally DET is a Schedule I drug under the ].<ref>{{cite web | author = International Narcotics Control Board | date = August 2003 |url= http://www.incb.org/pdf/e/list/green.pdf |title= List of psychotropic substances under international control |access-date=30 March 2007 |archive-url= https://web.archive.org/web/20070302130637/http://www.incb.org/pdf/e/list/green.pdf| archive-date= 2 March 2007 | url-status= live}}</ref>

===Australia===
DET 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 | work = Federal Register of Legislation | publisher = Australian Government | url = https://www.comlaw.gov.au/Details/F2015L01534 }}</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.

== See also ==
* ] * ]
* ] * ]
* ] * ]
* ]
* ]


== References == == References ==
{{reflist}} {{reflist}}


==External links== == External links ==
* *
* *
Line 74: Line 99:


{{Hallucinogenic tryptamines}} {{Hallucinogenic tryptamines}}
{{TiHKAL}}
{{Serotonergics}} {{Serotonergics}}
{{Tryptamines}} {{Tryptamines}}


] ]
]

]
]
]
]
]
]
]