5-Ethoxy-αMT

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5-EtO-AMT
5-EtO-AMT.svg
5-EtO-AET 3D BS.png
Identifiers
  • 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H18N2O
Molar mass 218.300 g·mol−1
3D model (JSmol)
  • CCOC1=CC2=C(C=C1)NC=C2CC(C)N
  • InChI=1S/C13H18N2O/c1-3-16-11-4-5-13-12(7-11)10(8-15-13)6-9(2)14/h4-5,7-9,15H,3,6,14H2,1-2H3
  • Key:RITFDCUITFOSHK-UHFFFAOYSA-N

5-Ethoxy-alpha-methyltryptamine (5-EtO-AMT) is a tryptamine derivative closely related to 5-MeO-AMT. It has an LD50 in mice of 56mg/kg, [1] but its pharmacology has otherwise been little studied. [2]

See also

Related Research Articles

<span class="mw-page-title-main">Alexander Shulgin</span> American medicinal chemist (1925–2014)

Alexander Theodore "Sasha" Shulgin was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamphetamine to psychologists in the late 1970s for psychopharmaceutical use and for the discovery, synthesis and personal bioassay of over 230 psychoactive compounds for their psychedelic and entactogenic potential.

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved."

<span class="mw-page-title-main">5-MeO-aMT</span> Chemical compound

5-MeO-aMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in ethanol.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">Diisopropyltryptamine</span> Chemical compound

Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.

<span class="mw-page-title-main">5-MeO-DALT</span> Chemical compound

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

<span class="mw-page-title-main">4-HO-MiPT</span> 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.

<i>N</i>-Methyltryptamine Chemical compound

N-Methyltryptamine (NMT) is a member of the substituted tryptamine chemical class and a natural product which is biosynthesized in the human body from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a common component in human urine. NMT is an alkaloid derived from L-tryptophan that has been found in the bark, shoots and leaves of several plant genera, including Virola, Acacia, Mimosa, and Desmanthus—often together with the related compounds N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).

<span class="mw-page-title-main">5-MeO-AET</span> Chemical compound

5-Methoxy-alpha-ethyltryptamine (5-MeO-α-ET) is a psychoactive drug and member of the tryptamine chemical class. It produces psychedelic and stimulant effects.

<span class="mw-page-title-main">Ethylisopropyltryptamine</span> Chemical compound

EiPT is a chemical in the tryptamine family, and produces psychedelic and hallucinogenic effects. It was probably first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">2C-O-4</span> Chemical compound

2C-O-4 (4-isopropoxy-2,5-dimethoxyphenethylamine) is a phenethylamine of the 2C family. It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. It produces hallucinogenic, psychedelic, and entheogenic effects. Because of the low potency of 2C-O-4, and the inactivity of 2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues.

<span class="mw-page-title-main">Lophophine</span> Chemical compound

Lophophine is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline.

<span class="mw-page-title-main">4-Hydroxy-5-methoxydimethyltryptamine</span> Chemical compound

4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a novel psychedelic drug. It is the 4-hydroxy counterpart of 5-MeO-DMT, or the 5-methoxy counterpart of psilocin.

<span class="mw-page-title-main">5-MeO-2-TMT</span> Chemical compound

5-Methoxy-2,N,N-trimethyltryptamine is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic. It was first synthesized by Alexander Shulgin and reported in his book TiHKAL. 5-MeO-TMT is claimed to show psychoactive effects at a dosage of 75–150 mg orally, but these are relatively mild compared to those of other similar compounds. This suggests that while the methyl group on the 2-position of the molecule has impaired the binding of metabolic enzymes like monoamine oxidase (MAO), it is also interfering with binding to and/or activation of the serotonin 5-HT2A receptor, the target responsible for mediating the hallucinogenic effects of such compounds.

<span class="mw-page-title-main">Dibutyltryptamine</span> 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.

<span class="mw-page-title-main">5-MeO-pyr-T</span> Chemical compound

5-MeO-pyr-T (5-methoxy-N,N-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 5-methoxy analog of pyr-T. 5-MeO-pyr-T was first synthesized by Hunt & Brimblecombe, who credited S. Mitzal for characterization of chemical properties. Later human tests were reported by Alexander Shulgin, in his book TiHKAL. An oral dosage of 0.5 to 2 mg, and an inhaled dosage of 2–3 mg are reported. 5-MeO-pyr-T causes varying reactions, such as amnesia, tinnitus, vomiting, and a 5-MeO-DMT-like rushing sensation. At the highest dosage reported in TiHKAL, the subject describes awakening from an apparent fugue state during which they were wandering the streets, with complete amnesia upon awakening.

<span class="mw-page-title-main">5-MeO-NMT</span> Chemical compound

5-MeO-NMT (5-methoxy-N-methyltryptamine) is an organic chemical compound, being the 5-methoxy analog of N-methyltryptamine (NMT). It was first isolated from Phalaris arundinacea. It has also been synthesized by Alexander Shulgin and reported in his book TiHKAL. Like other members of the N-methyltryptamine family of compounds, 5-MeO-NMT is believed to produce few or no psychedelic effects, although very little data exists about its pharmacological properties or toxicity.

<span class="mw-page-title-main">6-MeO-THH</span> Chemical compound

6-MeO-THH, or 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline derivative and a structural isomer of tetrahydroharmine (7-MeO-THH). 6-MeO-THH is mentioned in Alexander Shulgin's book TiHKAL, stating that 6-MeO-THH is very similar to the other carbolines. Limited testing suggests that it possesses mild psychoactive effects at 1.5 mg/kg and is said to be about one-third as potent as 6-methoxyharmalan. It has been isolated from certain plants of the Virola family.

<span class="mw-page-title-main">5-Ethoxy-DMT</span> 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.

<i>O</i>-Acetylbufotenine Chemical compound

O-Acetylbufotenine is a tryptamine derivative which produces psychedelic-appropriate responding in animal studies. It is an acylated derivative of bufotenine with higher lipophilicity that allows it to cross the blood–brain barrier; once inside the brain, it is metabolised to bufotenine. It also acts directly as an agonist at 5-HT1A and 5-HT1D receptors.

References

  1. U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#12316
  2. Shulgin A, Shulgin A. "a,O-DMS". TiHKAL #5.