Ariadne (drug)
Ariadne (drug)
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Ariadne (drug)

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Ariadne (drug)

Ariadne, also known chemically as 4C-D or 4C-DOM, by its developmental code name BL-3912, and by its former tentative brand name Dimoxamine, is a non-hallucinogenic psychoactive drug of the phenethylamine, phenylisobutylamine (α-ethylphenethylamine), and 4C families. It is a close analogue of the psychedelic drugs 2C-D and DOM, with 2C-D having no substitution at the α carbon, DOM having an α-methyl group, and Ariadne having an α-ethyl group. Ariadne is taken orally.

The drug is a serotonin 5-HT2 receptor partial agonist, including of the serotonin 5-HT2A receptor, similarly to psychedelics. However, Ariadne is not hallucinogenic in humans, but is still psychoactive, producing antidepressant and mild stimulant effects such as feelings of well-being and mental alertness. The drug shows dopaminergic actions in animals, such as increased motivation and reversal of parkinsonism, which may be mediated by serotonin 5-HT2A receptor activation-induced dopamine release in the brain. It is thought that the non-psychedelic nature of Ariadne with retained psychoactive effects is due to reduced but still high efficacy at the serotonin 5-HT2A receptor relative to psychedelics.

Ariadne was first synthesized by Alexander Shulgin in 1968 and its psychoactive effects were discovered by Shulgin in 1969. It was developed as a potential pharmaceutical drug at Bristol Laboratories, for instance as an antidepressant and for various other uses, and entered clinical trials around 1974. The drug reached phase 3 trials prior to its development being shelved. The development of Ariadne is said to have been discontinued for strategic economic reasons rather than due to issues with effectiveness or safety. There has been renewed interest in Ariadne and similar drugs in the 2020s owing to increased interest in psychedelics for treatment of psychiatric disorders. Ariadne is not an explicitly controlled substance in the United States, but may be considered Schedule I as an isomer of DOET.

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin reported human tests of Ariadne at doses of up to 32 mg orally, finding that it produced "the alert of a psychedelic, with none of the rest of the package". Very little published data exists about the human pharmacology of Ariadne apart from Shulgin's limited testing; unpublished human trials reportedly observed some psychoactive effects, but no hallucinogenic effects. Ariadne is one of Shulgin's "ten classic ladies", a series of methylated DOM derivatives.

In his book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds, Shulgin described (R)-Ariadne as increasing mental alertness and producing feelings of well-being at doses of 25 to 50 mg orally. It was claimed to improve symptoms of manic depression in psychotic individuals at doses of 50 to 100 mg orally and to improve symptoms of Parkinson's disease at a dosage of 100 mg/day orally. Doses of up to 300 mg resulted in an altered state of consciousness but still no psychedelic effects. For comparison, DOM shows psychoactive sub-hallucinogenic effects at doses of 1 to 3 mg orally and psychedelic effects at doses of more than 3 mg orally.

The effects of Ariadne have been said to have a duration of 2 to 5 hours.

Another related drug with similar psychoactive effects as Ariadne is thiobuscaline.

Ariadne, as the (R)- enantiomer, is active at doses as low as 25 mg and was tested in clinical trials at doses of 50 to 100 mg. Doses as high as 300 mg have been assessed, more than 10 times higher than the minimum reported active dose. No psychedelic effects occurred at this or lower doses, but therapeutic effects were observed.

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