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Ariadne (drug)

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Ariadne
Names
IUPAC name
1-(2,5-Dimethoxy-4-methylphenyl)butan-2-amine
Other names
4-Methyl-2,5-dimethoxy-alpha-ethylphenethylamine
4-Methyl-2,5-dimethoxybutanamine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H21NO2/c1-5-11(14)7-10-8-12(15-3)9(2)6-13(10)16-4/h6,8,11H,5,7,14H2,1-4H3 checkY
    Key: MLYCFWZIAJAIGW-UHFFFAOYSA-N checkY
  • InChI=1/C13H21NO2/c1-5-11(14)7-10-8-12(15-3)9(2)6-13(10)16-4/h6,8,11H,5,7,14H2,1-4H3/t11-/m1/s1
    Key: MLYCFWZIAJAIGW-LLVKDONJBY
  • InChI=1/C13H21NO2/c1-5-11(14)7-10-8-12(15-3)9(2)6-13(10)16-4/h6,8,11H,5,7,14H2,1-4H3
    Key: MLYCFWZIAJAIGW-UHFFFAOYAX
  • O(c1cc(c(OC)cc1C[C@H](N)CC)C)C
  • O(c1cc(c(OC)cc1CC(N)CC)C)C
Properties
C13H21NO2
Molar mass 223.316 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ariadne (also known as 4C-D, 4C-DOM, α-Et-2C-D, BL-3912, or dimoxamine) is a lesser-known psychedelic drug. It is a homologue of 2C-D and DOM. Ariadne was first synthesized by Alexander Shulgin. In his book PiHKAL, Shulgin reported testing Ariadne up to a dose of 32 mg, and reported that it produces psychedelia at a bare threshold.[1] Very little data exists about the pharmacological properties, metabolism, and toxicity of Ariadne in humans apart from Shulgin's limited testing.

In more an animal study, Ariadne was shown to produce stimulus generalization in rats trained to respond to the drug MDMA.[2]

See also

References

  1. ^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ Glennon RA (1993). "MDMA-like stimulus effects of alpha-ethyltryptamine and the alpha-ethyl homolog of DOM". Pharmacol Biochem Behav. 46 (2): 459–462. PMID 7903460.