Diethyltryptamine

DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET.^[2][3]

Diethyltryptamine

Clinical data
Other names	DET; N,N-Diethyltryptamine; T-9; T9
Routes of administration	Oral
Drug class	Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule III DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I UN: Psychotropic Schedule I
Pharmacokinetic data
Duration of action	2–4 hours[2]
Identifiers
IUPAC name N,N-diethyl-2-(1H-indol-3-yl)ethan-2-amine
CAS Number	61-51-8 Y
PubChem CID	6090
DrugBank	DB01460 Y
ChemSpider	5865 Y
UNII	916E8V4S2V
KEGG	C22726
ChEMBL	ChEMBL142936 Y
CompTox Dashboard (EPA)	DTXSID9052763
Chemical and physical data
Formula	C14H20N2
Molar mass	216.328 g·mol−1
3D model (JSmol)	Interactive image
Melting point	169 to 171 °C (336 to 340 °F)
SMILES CCN(CC)CCC1=CNC2=C1C=CC=C2
InChI InChI=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 Y Key:LSSUMOWDTKZHHT-UHFFFAOYSA-N Y
(verify)

DET, alongside DMT, was placed into the UN Schedule 1 list of illegal drugs in the 1970s, and is uncommon now.^{[citation needed][4]}

Use

DET is active at an oral dose of around 50 to 100 mg and the effects last for about 2 to 4 hours.^[2][5]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

The mechanism of action of DET is thought to be serotonin receptor agonism, much like other classic psychedelics.^[6] It is a serotonin 5-HT_2A receptor agonist.^[7] The drug produces the head-twitch response in rodents, a behavioral proxy of psychedelic-like effects.^[5]

Pharmacokinetics

Unlike DMT, DET is orally active as it is not subject to extensive metabolism by monoamine oxidase A. This may be due to the increased steric bulk of the N-ethyl substituents relative to the respective methyl groups of DMT. This is also true for many other tryptamines with larger nitrogen substituents.^{[citation needed]}

Chemistry

DET is a homolog of the common tryptamine hallucinogen N,N-dimethyltryptamine (DMT).

History

DET was first described in the scientific literature by 1959.^[8] It was first synthesized by Stephen Szára and was assessed pharmacologically by Borsi and Lenart.^[8]

Society and culture

Legal status

International

Internationally DET is a Schedule I drug under the Convention on Psychotropic Substances.^[4]

Australia

DET is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).^[9] 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.

Research

Psychosis model

Early studies of DET as well as other psychedelics were focused on their presumed psychotomimetic properties.^[10] Researchers theorized that abnormal metabolites of endogenous chemicals such as tryptamine, serotonin, and tryptophan could be the explanation for mental disorders such as schizophrenia, or psychosis.^[11] With the progression of science and pharmacological understanding, this belief has been dismissed by most researchers^{[citation needed]}.

Mushroom production

Although DET is a synthetic compound with no known natural sources, it has been used in conjunction with the mycelium of Psilocybe cubensis to biosynthetically produce the chemicals ethocybin (4-PO-DET) and ethocin (4-HO-DET). Isolation of the alkaloids resulted in 3.3% ethocybin and 0.01-0.8% ethocin.^[12]

See also

• 4-HO-DET (ethocin)
• Ethocybin (4-PO-DET)
• 5-MeO-DET
• 5-HO-DET