Ariadne (psychedelic)

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.

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
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • 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 Y
    Key: MLYCFWZIAJAIGW-UHFFFAOYSA-N Y
  • 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
SMILES
  • O(c1cc(c(OC)cc1C[C@H](N)CC)C)C
  • O(c1cc(c(OC)cc1CC(N)CC)C)C
Properties
Chemical formula
 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).
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Infobox references

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.


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