Allylescaline

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Allylescaline
Allylescaline.svg
Allylescaline-3d-sticks.png
Names
Preferred IUPAC name
2-{3,5-Dimethoxy-4-[(prop-2-en-1-yl)oxy]phenyl}ethan-1-amine
Other names
2-[4-(Allyloxy)-3,5-dimethoxyphenyl]ethan-1-amine
2-[4-(Allyloxy)-3,5-dimethoxyphenyl]ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H19NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3 X mark.svgN
    Key: JNUAYHHGCXYBHX-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C13H19NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3
    Key: JNUAYHHGCXYBHX-UHFFFAOYAR
  • COc1cc(cc(OC)c1OCC=C)CCN
Properties
C13H19NO3
Molar mass 237.299 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] The compound was later synthesized by Alexander Shulgin and further described in his book PiHKAL . [2] The dosage range is listed as 20–35 mg, and the duration 8–12 hours. [2] 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.

Contents

Allylescaline is illegal in Sweden as of January 2016. [3]

See also

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Methallylescaline (4-Methylallyloxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. It is the 4-methyl analog of allylescaline. Methallylescaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 40–65 mg and the duration is listed as 12–16 hours. Little data exists about the pharmacological properties, metabolism, and toxicity of methallylescaline, though it is known to be an agonist of 5-HT2A receptors, with effects comparable to that of other mescaline analogs and has been sold as a designer drug.

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3C-AL (4-Allyloxy-3,5-dimethoxyamphetamine) is a psychedelic phenethylamine with structural similarities to allylescaline. Little information exists on the human pharmacology of 3C-AL and it has little-to-no history of human use. It can be synthesized from syringaldehyde by reaction with allyl iodide followed by condensation with nitroethane and reduction. The hydrochloride salt is a white crystal with a melting point of 180–181°C.

References

  1. Leminger, Otakar (1972). "The Chemistry of Alkoxylated Phenethylamines – Part 2". Chemický Průmysl. 22: 553.
  2. 1 2 AL Entry in PiHKAL
  3. "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.