Diethyltryptamine

Diethyltryptamine
Systematic (IUPAC) name
N,N-diethyl-2-(1H-indol-3-yl)ethanamine
Clinical data
Pregnancy cat.  ?
Legal status  ? (UK) Schedule I (US)
Identifiers
CAS number 7558-72-7
ATC code None
PubChem CID 6090
DrugBank DB01460
ChemSpider 5865 Y
ChEMBL CHEMBL142936 Y
Chemical data
Formula C14H20N2 
Mol. mass 216.32 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 169–171 °C (336–340 °F)
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DET, also known under its chemical name N,N-diethyltryptamine and as T-9,[1] is a psychedelic drug closely related to DMT and 4-HO-DET. However, despite its structural similarity to DMT it is active orally around 50–100 mg without the aid of MAO inhibitors lasting about 2–4 hours.

Contents

Chemistry

DET is an analogue of the common tryptamine hallucinogen N,N-Dimethyltryptamine or DMT. DET is sometimes preferred over DMT because it can be taken orally whereas DMT cannot. This is because the enzyme monoamine oxidase 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

The mechanism of action is thought to be serotonin receptor agonism, much like other classic psychedelics.[2]

Biochemistry

Though DET is a synthetic compound with no known natural sources it has been used with mycelium of Psilocybe cubensis to produce the synthetic chemicals 4-PO-DET (Ethocybin) and 4-HO-DET (Ethocin), as opposed the naturally occurring 4-PO-DMT (Psilocybin) and 4-HO-DMT (Psilocin). Isolation of the alkaloids resulted in 3.3% 4-HO-DET and 0.01-0.8% 4-PO-DET.[3]

Psychosis model

Early studies of DET, as well as other psychedelics, mainly focused on the believed psychotomimetic properties.[4] Researchers theorized that abnormal metabolites of endogenous chemicals such as tryptamine, serotonin, and tryptophan could be the explanation for mental disorders as schizophrenia, or psychosis.[5] With the progression of science and pharmacological understanding this belief has been dismissed by most researchers.

See also

References

  1. ^ "Erowid DET Vault : Chemistry". http://www.erowid.org/chemicals/det/det_chemistry.shtml. Retrieved 2008-01-08. 
  2. ^ Winter JC (September 1969). "Behavioral effects of N,N-diethyltryptamine: absence of antagonism by xylamidine tosylate". J. Pharmacol. Exp. Ther. 169 (1): 7–16. PMID 5306645. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=5306645. 
  3. ^ Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". J. Basic Microbiol. 29 (6): 347–52. doi:10.1002/jobm.3620290608. PMID 2614674. 
  4. ^ "PSILOCYBIN AND DIETHYLTRYPTAMINE: TWO TRYPTAMINE HALLUCINOGENS". http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=2633. Retrieved 2008-01-03. 
  5. ^ "Effects of LSD-25, N,N-Dimethyltryptamine (DMT), and N,N-Diethyltryptamine (DET) on the Photic Evoked Responses in the unanesthetized Rabbit". http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=2360. Retrieved 2008-01-03. 

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Drugs from TiHKAL

2-Methyl-5-HT • 4-Acetoxy-DET • 4-Acetoxy-DiPT • 4-Acetoxy-DMT • 4-Acetoxy-MiPT • 4-AcO-MET • 4-HO-αMT • 4-HO-DiPT • 4-HO-MET • 4-MeO-DMT • 4-Methyl-αET • 4-Methyl-αMT • 4,5-DHP-DMT • 4,5-MDO-DMT • 4,5-MDO-DIPT • 5-Benzyloxytryptamine • 5-Bromo-DMT • 5-Carboxamidotryptamine • 5-Ethoxy-αMT • 5-Fluoro-αMT • 5-HO-αMT • 5-HTP • 5-Ethoxy-DMT • 5-Ethyl-DMT • 5-Fluoro-DMT • 5-Methyl-DMT • 5-Methoxytryptamine • 5-MeO-7,N,N-TMT • 5-Methyl-αET • 5-MeO-αET  • 5-MeO-αMT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MALT • 5-MeO-MiPT • 5-MeO-NBpBrT • 5,7-Dihydroxytryptamine • 5-(Nonyloxy)tryptamine • 6-Fluoro-αMT • 7-Methyl-αET • 7-Methyl-DMT • αET • αMT • Aeruginascin • AL-37350A • BW-723C86 • Baeocystin • Bufotenidine • Bufotenin • DALT • Desformylflustrabromine • DET • DiPT • DMT • DPT • Ethocybin • EiPT • EMDT • EPT • Ethocin • FGIN-127 • FGIN-143 • Ibogaine • Indorenate • Iprocin • MET • MiPT • MPT • Miprocin • Melatonin • MS-245 • NAS • NMT • Norbaeocystin • Normelatonin • Oxypertine • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan • Yohimbine • Yuremamine • Zolmitriptan