Diethyltryptamine

Diethyltryptamine
Clinical data
ATC code	none;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule III; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name N,N-diethyl-2-(1H-indol-3-yl)ethan-2-amine;
CAS Number	61-51-8 ;
PubChem CID	6090;
DrugBank	DB01460 ;
ChemSpider	5865 ;
UNII	916E8V4S2V;
KEGG	C22726;
ChEMBL	ChEMBL142936 ;
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 ; Key:LSSUMOWDTKZHHT-UHFFFAOYSA-N ;
	(what is this?) (verify)

DET, also known under its chemical name N,N-diethyltryptamine and as T-9,^[2] is a psychedelic drug closely related to DMT and 4-HO-DET. However, despite its structural similarity to DMT, its activity is induced by an oral dose of around 50–100 mg, without the aid of MAO inhibitors, and the effects last for about 2–4 hours.

Chemistry

DET is an analogue of the common tryptamine hallucinogen N,N-Dimethyltryptamine or DMT.

Pharmacology

The mechanism of action is thought to be serotonin receptor agonism, much like other classic psychedelics.^[3]

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, 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.

Biochemistry

Although DET is a synthetic compound with no known natural sources, it has been used in conjunction with the mycelium of Psilocybe cubensis to produce the synthetic chemicals 4-PO-DET (Ethocybin) and 4-HO-DET (Ethocin), as opposed to 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.^[4]

Psychosis model

Early studies of DET as well as other psychedelics were focused on their presumed psychotomimetic properties.^[5] 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.^[6] With the progression of science and pharmacological understanding, this belief has been dismissed by most researchers.

Legal status

Internationally DET is a Schedule I drug under the Convention on Psychotropic Substances.^[7]

Australia

DET is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).^[8] 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.

References

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ "Erowid DET Vault : Chemistry". Retrieved 2008-01-08.
^ Winter JC (September 1969). "Behavioral effects of N,N-diethyltryptamine: absence of antagonism by xylamidine tosylate". The Journal of Pharmacology and Experimental Therapeutics. 169 (1): 7–16. PMID 5306645.
^ Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". Journal of Basic Microbiology. 29 (6): 347–52. doi:10.1002/jobm.3620290608. PMID 2614674. S2CID 43308695.
^ Böszörmenyi Z (1960). "Psilocybin and diethyltryptamine: Two tryptamine hallucinogens". Neuro-psychopharm. 2: 226–9.
^ Khazan N, McCash D (April 1965). "Effects of LSD-25, n,n-dimethyltryptamine (DMT), and N,N-diethyltryptamine (DET) on the photic evoked responses in the unanesthetized rabbit". Archives Internationales de Pharmacodynamie et de Therapie. 154 (2): 474–83. PMID 5839429.
^ International Narcotics Control Board (August 2003). "List of psychotropic substances under international control" (PDF). Archived (PDF) from the original on 2 March 2007. Retrieved 30 March 2007.
^ "Poisons Standard". Federal Register of Legislation. Australian Government. October 2015.

External links

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[titleErowid_DET_Vault_:_Chemistry-2] "Erowid DET Vault : Chemistry". Retrieved 2008-01-08.

[3] Winter JC (September 1969). "Behavioral effects of N,N-diethyltryptamine: absence of antagonism by xylamidine tosylate". The Journal of Pharmacology and Experimental Therapeutics. 169 (1): 7–16. PMID 5306645.

[4] Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". Journal of Basic Microbiology. 29 (6): 347–52. doi:10.1002/jobm.3620290608. PMID 2614674. S2CID 43308695.

[titlePSILOCYBIN_AND_DIETHYLTRYPTAMINE:_TWO_TRYPTAMINE_HALLUCINOGENS-5] Böszörmenyi Z (1960). "Psilocybin and diethyltryptamine: Two tryptamine hallucinogens". Neuro-psychopharm. 2: 226–9.

[pmid5839429-6] Khazan N, McCash D (April 1965). "Effects of LSD-25, n,n-dimethyltryptamine (DMT), and N,N-diethyltryptamine (DET) on the photic evoked responses in the unanesthetized rabbit". Archives Internationales de Pharmacodynamie et de Therapie. 154 (2): 474–83. PMID 5839429.

[7] International Narcotics Control Board (August 2003). "List of psychotropic substances under international control" (PDF). Archived (PDF) from the original on 2 March 2007. Retrieved 30 March 2007.

[Poisons_Standard-8] "Poisons Standard". Federal Register of Legislation. Australian Government. October 2015.

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