TME (psychedelics)

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TME, or thio metaescaline , is a series of lesser-known psychedelic drugs similar in structure to mescaline. Their structures are based on that of metaescaline. They were first synthesized by Alexander Shulgin and recorded in his book PiHKAL (Phenethylamines i Have Known And Loved) . Very little is known about their dangers or toxicity.

Contents

TME compounds

3-TME
3-TME.svg
Names
IUPAC name
2-[3-(Ethylsulfanyl)-4,5-dimethoxyphenyl]ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • Key: WHUXWWJFRBXUOQ-UHFFFAOYSA-N
  • InChI=1S/C12H19NO2S/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3
  • CCSC1=CC(=CC(=C1OC)OC)CCN
Properties
C12H19NO2S
Molar mass 241.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Dosage: 60–100 mg
Duration: 10–15 hours
Effects: Strong entheogenic action, reduction of inhibition
4-TME
4-TME.svg
Names
IUPAC name
2-[3-Ethoxy-5-methoxy-4-(methylsulfanyl)phenyl]ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • Key: ACLYMWAQSAEILP-UHFFFAOYSA-N
  • InChI=1S/C12H19NO2S/c1-4-15-11-8-9(5-6-13)7-10(14-2)12(11)16-3/h7-8H,4-6,13H2,1-3H3
  • CCOc1cc(cc(c1SC)OC)CCN
Properties
C12H19NO2S
Molar mass 241.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Dosage: 60–100 mg
Duration: 10–15 hours
Effects: Few to none
5-TME
5-TME.svg
Names
IUPAC name
2-[3-Ethoxy-4-methoxy-5-(methylsulfanyl)phenyl]ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • Key: BRABKKMYSDDDCR-UHFFFAOYSA-N
  • InChI=1S/C12H19NO2S/c1-4-15-10-7-9(5-6-13)8-11(16-3)12(10)14-2/h7-8H,4-6,13H2,1-3H3
  • CCOc1cc(cc(c1OC)SC)CCN
Properties
C12H19NO2S
Molar mass 241.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Dosage: greater than 200 mg
Duration: unknown
Effects: Few to none

See also

Related Research Articles

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

PiHKAL: A Chemical Love Story is a book by 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".

Trimethoxyamphetamines (TMAs) are a family of positionally isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the positions of the three methoxy groups: TMA (TMA-1), TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are substituted amphetamines and are analogues of the phenethylamine cactus alkaloid mescaline and the DOx drugs.

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

Proscaline is a psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In PiHKAL, Alexander Shulgin reports that a dose of 30–60 mg produces effects lasting 8–12 hours.

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

2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.

<span class="mw-page-title-main">2,4,5-Trimethoxyphenethylamine</span> Chemical compound

2,4,5-Trimethoxyphenethylamine, also known as 2C-O or 2C-OMe, or is a phenethylamine of the 2C family and was first synthesized by Jansen in 1931. It is a positional isomer of the drug mescaline (3,4,5-trimethoxy).

<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">Isoproscaline</span> Chemical compound

Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is an analog of mescaline. It is closely related to proscaline and was first synthesized by David E. Nichols. It produces hallucinogenic, psychedelic, and entheogenic effects.

<span class="mw-page-title-main">TIM (psychedelics)</span> Series of psychedelic drugs

TIM, or thioisomescaline, is a series of lesser-known psychedelic drugs similar in structure to mescaline. They were first synthesized by Alexander Shulgin. In his book PiHKAL , none of their durations are known. Very little is known about their dangers or toxicity.

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

Asymbescaline (3,4-diethoxy-5-methoxyphenethylamine) is a lesser-known psychedelic drug. It is a homolog of mescaline. Asymbescaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 200–280 mg, and the duration listed as 10–15 hours. Asymbescaline produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of asymbescaline.

TASB, or thioasymbescaline, is a series of lesser-known psychedelic drugs similar in structure to asymbescaline and to mescaline. They were first synthesized by Alexander Shulgin and written up in his book PiHKAL . Very little is known about their dangers or toxicity.

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

Buscaline (3,5-dimethoxy-4-butoxyphenethylamine) is a chemical compound prepared as a possible psychedelic drug. It is an analog of mescaline. Buscaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 150 mg, and the duration is "several hours". Buscaline produces no psychedelic or psychoactive effects, but causes heart arrhythmia and light diarrhea. It does not cause any visuals or insights. Very little data exists about the pharmacological properties, metabolism, and toxicity of buscaline.

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

Phenescaline, or 3,5-dimethoxy-4-phenylethoxyphenethylamine, is a lesser-known psychedelic drug. It is an analogue of mescaline. Alexander Shulgin first synthesized Phenescaline. In his book PiHKAL , the minimum dosage is listed as 150 mg, and the duration is unknown. Phenescaline produces a threshold effect. Very little data exists about the pharmacological properties, metabolism, and toxicity of phenescaline.

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

Metaescaline (3,4-dimethoxy-5-ethoxyphenethylamine) is a lesser-known psychedelic drug. It is an analog of mescaline. Metaescaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 200–350 mg, and the duration listed as 8–12 hours. Metaescaline produces mental insights, entactogenic, MDMA-like effects, and TOMSO-like activation. Little data exists about the pharmacological properties, metabolism, and toxicity of metaescaline, though it has been studied to a limited extent in comparison with other related compounds.

α-Ethylmescaline Chemical compound

α-Ethylmescaline is a lesser-known psychedelic drug. It is an analog of mescaline. AEM was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 220 mg, and the duration unknown. AEM produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of AEM.

<span class="mw-page-title-main">Allylescaline</span> Psychedelic drug

Allylescaline (4-allyloxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. It is closely related in structure to mescaline. Allylescaline was first synthesized by Otakar Leminger in 1972. The compound was later synthesized by Alexander Shulgin and further described in his book PiHKAL. The dosage range is listed as 20–35 mg, and the duration 8–12 hours. Allylescaline produces an entactogenic warmth, an entheogenic effect, and a feeling of flowing energy. Very little data exists about the pharmacological properties, metabolism, and toxicity of allylescaline.

<span class="mw-page-title-main">3,4-Dimethoxyphenethylamine</span> Chemical compound

3,4-Dimethoxyphenethylamine (DMPEA) is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine and to 3,4-dimethoxyamphetamine (3,4-DMA).

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

TSB, or thiosymbescaline, is a series of lesser-known psychedelic drugs similar in structure to symbescaline. They were first synthesized by Alexander Shulgin and written up in his book PiHKAL . Very little is known about their dangers or toxicity.

Thiotrisescaline (T-TRIS) is a series of lesser-known phenethylamines prepared as potential psychedelic drugs. There are two isomers, 3-T-TRIS and 4-T-TRIS, each similar in structure to trisescaline with a sulfur atom in a place of a different oxygen atom. They were first synthesized by Alexander Shulgin and described in his book PiHKAL. Very little is known about their dangers or toxicity.

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

Thioproscaline, or 3,5-dimethoxy-4-propylthiophenethylamine, is a lesser-known psychedelic drug. It is the 4-propylthio analog of mescaline. Thioproscaline was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage range is listed as 20–25 mg, and the duration listed as 10–15 hours. Thioproscaline causes closed-eye visuals, slight open-eye visuals, and a body load. Very little data exists about the pharmacological properties, metabolism, and toxicity of thioproscaline.

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

2C-Se is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL. Shulgin considered 2C-Se to be around three times the potency of mescaline, but was too concerned about toxicity to test it extensively, though he considered it noteworthy as the only psychedelic drug to contain a selenium atom.