5-MeO-DBT

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5-MeO-DBT
5-MeO-DBT.svg
Identifiers
  • N-Butyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]butan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H30N2O
Molar mass 302.462 g·mol−1
3D model (JSmol)
  • CCCCN(CCCC)CCC1=CNC2=C1C=C(C=C2)OC
  • InChI=1S/C19H30N2O/c1-4-6-11-21(12-7-5-2)13-10-16-15-20-19-9-8-17(22-3)14-18(16)19/h8-9,14-15,20H,4-7,10-13H2,1-3H3
  • Key:WVGCRISHWANOTO-UHFFFAOYSA-N

5-MeO-DBT (5-Methoxy-N,N-dibutyltryptamine, 5-MeO-BET) is a rare substituted tryptamine derivative, which is thought to be a psychoactive substance and was identified in a designer drug sample by a forensic laboratory in Slovenia in March 2021, [1] although only analytical studies have been conducted and no pharmacological data is available. [2] [3] [4] It is nevertheless controlled under drug analogue legislation in a number of jurisdictions.

See also

Related Research Articles

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5-MeO-DMT Chemical compound

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Sonoran Desert toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, The power, and Toad venom.

Psilocin Psychedelic substance

Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.

Diethyltryptamine Chemical compound

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. 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.

5-MeO-DALT Chemical compound

5-MeO-DALT or N,N-di allyl-5-methoxy tryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.

4-HO-MiPT Chemical compound

4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

5,N,N-TMT Chemical compound

5,N,N-trimethyltryptamine is a tryptamine derivative that is a psychedelic drug. It was first made in 1958 by E. H. Young. In animal experiments it was found to be in between DMT and 5-MeO-DMT in potency which would suggest an active dosage for humans in the 20–60 mg range. Human psychoactivity for this compound has been claimed in reports on websites such as Erowid but has not been independently confirmed.

Dibutyltryptamine Chemical compound

N,N-Dibutyltryptamine (DBT) is a psychedelic drug belonging to the tryptamine family. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base. DBT was first synthesized by the chemist Alexander Shulgin and reported in his book TiHKAL . Shulgin did not test DBT himself, but reports a human dosage of "1 mg/kg i.m." being active, but less so than DMT or DET. This suggests that an active dosage of DBT will be in the 100 mg range. This compound has been sold as a "research chemical" and has been confirmed to be an active hallucinogen although somewhat weaker than other similar tryptamine derivatives. It produces a head-twitch response in mice.

Dimemebfe

Dimemebfe (5-MeO-BFE) is a recreational drug and research chemical. It acts as an agonist for the 5-HT1A and 5-HT2 family of serotonin receptors. It is related in structure to the psychedelic tryptamine derivative 5-MeO-DMT, but with the indole nitrogen replaced by oxygen, making dimemebfe a benzofuran derivative. It is several times less potent as a serotonin agonist than 5-MeO-DMT and with relatively more activity at 5-HT1A, but still shows strongest effects at the 5-HT2 family of receptors.

DALT Chemical compound

N,N-Diallyltryptamine (DALT) is a tryptamine derivative which has been identified as a new psychoactive substance. It has been used as an intermediate in the preparation of radiolabeled diethyltryptamine.

5-Ethoxy-DMT Chemical compound

5-Ethoxy-DMT is a tryptamine derivative which has been previously synthesized as a chemical intermediate, but has not been studied to determine its pharmacology.

Methylpropyltryptamine Chemical compound

Methylpropyltryptamine is a tryptamine. It is a homolog of methylethyltryptamine.

6-MAPB

6-MAPB is a psychedelic and entactogenic drug which is structurally related to 6-APB and MDMA. It is not known to have been widely sold as a "designer drug" but has been detected in analytical samples taken from individuals hospitalised after using drug combinations that included other benzofuran derivatives. 6-MAPB was banned in the UK in June 2013, along with 9 other related compounds which were thought to produce similar effects.

4-HO-DSBT Chemical compound

4-HO-DsBT (4-hydroxy-N,N-di-sec-butyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist. It was first made by Alexander Shulgin and is mentioned in his book TiHKAL, but was never tested by him. However it has subsequently been tested in vitro and unlike the n-butyl and isobutyl isomers which are much weaker, the s-butyl derivative retains reasonable potency, with a similar 5-HT2A receptor affinity to MiPT but better selectivity over the 5-HT1A and 5-HT2B subtypes.

5-HO-DiPT

5-HO-DiPT (5-hydroxy-N,N-di-iso-propyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist. It is primarily known as a metabolite of the better known psychoactive drug 5-MeO-DiPT, but 5-HO-DiPT has also rarely been encountered as a designer drug in its own right. Tests in vitro show 5-HO-DiPT to have high 5-HT2A affinity and good selectivity over 5-HT1A, while being more lipophilic than the related drug bufotenine (5-HO-DMT), which produces mainly peripheral effects.

QMPSB Chemical compound

QMPSB is an arylsulfonamide-based synthetic cannabinoid that has been sold as a designer drug.

ECPLA

ECPLA (N-ethyl-N-cyclopropyllysergamide) is an analog of lysergic acid diethylamide (LSD) developed by Synex Synthetics. In studies in mice, it was found to have approximately 40% the potency of LSD.

3-Methyl-PCP

3-Methyl-PCP is a recreational designer drug with dissociative effects. It is an arylcyclohexylamine derivative, related to drugs such as 3'-MeO-PCP and 3'-Me-PCPy. It was first synthesised in the 1960s, but was only identified on the illicit market in Hungary in September 2020, and was made illegal in Hungary in April 2021.

MALT (psychedelic drug)

MALT is a lesser-known drug from the tryptamine family. It is a novel compound with very little history of human use. It is closely related to methylpropyltryptamine (MPT), as well as N-methyltryptamine. It has been sold online as a designer drug. Very little information on the pharmacology or toxicity of MALT is available.

References

  1. "Analytical Report. 5-MeO-DBT" (PDF). Slovenia: Nacionalni Forenzični Laboratorij. 10 March 2021.
  2. Brandt SD, Freeman S, Fleet IA, McGagh P, Alder JF (2005). "Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR". Analyst. 130 (3): 330–344. doi:10.1039/b413014f.
  3. Brandt SD, Freeman S, Fleet IA, Alder JF (2005). "Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS". Analyst. 130 (9): 1258–1262. doi:10.1039/b504001a.
  4. Brandt SD, Martins CP (2010). "Analytical methods for psychoactive N,N-dialkylated tryptamines". Trends Anal. Chem. 29 (8): 858–869. doi:10.1016/j.trac.2010.04.008.