Ariadne (psychedelic)

Ariadne (psychedelic)

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	52842-59-8 Y
3D model (Jmol)	Interactive image Interactive image
ChemSpider	148565 Y
PubChem	169886
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	223.31 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Ariadne, 4C-D, 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 (Phenethylamines i Have Known And Loved), Shulgin reported testing Ariadne up to a dose of 32 mg, and reported that it produces psychedelia at a bare threshold. Very little data exists about the pharmacological properties, metabolism, and toxicity of Ariadne in humans apart from Shulgin's limited testing.

However, in more recent animal studies, 4C-D was shown to produce stimulus generalisation in rats trained to respond to the drug MDMA. This suggests that while 4C-D may lack hallucinogenic effects, it might potentially produce empathogenic effects similar to those of MDMA if used at higher dose ranges, beyond those trialled by Shulgin (the potency of 4C-D in this study was similar to that of MDMA, 1.5 mg/kg, which would equate to a dose of ~100 mg in a human).