Ariadne (psychedelic)
Encyclopedia
Ariadne or 4-methyl-2,5-dimethoxy
Methoxy
In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...

-alpha-ethyl
Ethyl group
In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....

phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...

, is a lesser-known psychedelic drug
Psychedelics, dissociatives and deliriants
This general group of pharmacological agents can be divided into three broad categories: psychedelics, dissociatives, and deliriants. These classes of psychoactive drugs have in common that they can cause subjective changes in perception, thought, emotion and consciousness...

. It is a homologue of 2C-D
2C-D
2C-D is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. The full name of the chemical is...

 and DOM
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...

. Ariadne was first synthesized by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...

. In his book PiHKAL (Phenethylamines i Have Known And Loved)
PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...

, Shulgin reported testing Ariadne up to a dose of 32 mg, and reported that it produces psychedelia and 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, α-Et-DOM was shown to produce stimulus generalisation in rats trained to respond to the drug MDMA. This suggests that while α-Et-DOM 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 α-Et-DOM 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).

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