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Ariadne (drug)

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Ariadne
Clinical data
Other names4-Methyl-2,5-dimethoxy-α-ethylphenethylamine; 4-Methyl-2,5-dimethoxybutanamine; 4C-D; 4C-DOM; α-Et-2C-D; BL-3912; Dimoxamine
Drug classSerotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor agonist; Non-hallucinogenic serotonin 5-HT2A receptor agonist
Identifiers
  • 1-(2,5-dimethoxy-4-methylphenyl)butan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO2
Molar mass223.316 g·mol−1
3D model (JSmol)
  • O(c1cc(c(OC)cc1C[C@H](N)CC)C)C
  • 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
  (verify)

Ariadne (also known as 4C-D, 4C-DOM, α-Et-2C-D, BL-3912, or dimoxamine) is a little-known psychoactive drug of the substituted phenethylamine family.[1] It is a homologue of the psychedelics 2C-D and DOM.[1]

The drug is a serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[2] However, it is non-hallucinogenic in animals and humans, although it still has some psychoactive effects.[2][1] It may be non-hallucinogenic due to biased agonism of the serotonin 5-HT2A receptor.[2]

Ariadne was developed by Alexander Shulgin.[1] It was studied at Bristol Laboratories as an antidepressant but was never marketed.[3]

Effects

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In his 1991 book PiHKAL, Alexander Shulgin reported testing Ariadne on himself up to a dose of 32 mg, finding that it produced "the alert of a psychedelic, with none of the rest of the package".[1] Very little published data exists about the human pharmacology of Ariadne apart from Shulgin's limited testing; unpublished human trials reportedly observed some psychoactive effects, but no hallucinations.[4][2]

Pharmacology

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Ariadne is a potent and selective agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[2] However, it is less efficacious in activating the serotonin 5-HT2A receptor, including the Gq, G11, and β-arrestin2 signaling pathways, compared to the related drug DOM.[2]

Ariadne shows a markedly attenuated head-twitch response, a behavioral proxy of psychedelic effects, in animals.[2] It is thought that the reduced efficacy of Ariadne in activating the serotonin 5-HT2A receptor is responsible for its non-hallucinogenic nature.[2] Ariadne was also shown to produce stimulus generalization in rats trained to respond to MDMA[5] or LSD.[4]

Chemistry

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The (R)-enantiomer of Ariadne is known as BL-3912A.[2]

History

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Ariadne was first synthesized by Alexander Shulgin.[1] Shulgin reported that the drug was tested by Bristol Laboratories as an antidepressant, in an anecdote where he was explaining how human testing is invaluable (compared to animal testing) on drugs that change the state of the mind. He said, "Before they launched into a full multi-clinic study to determine whether it's going to be worth the animal studies or not, every person on the board of directors took it."[3]

See also

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References

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  1. ^ a b c d e f Shulgin AT, Shulgin A (1991). PiHKAL: a chemical love story (1st ed.). Berkeley, CA: Transform Press. ISBN 9780963009609. OCLC 25627628.
  2. ^ a b c d e f g h i Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, et al. (January 2023). "Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs". ACS Chemical Neuroscience. 14 (1): 119–135. doi:10.1021/acschemneuro.2c00597. PMC 10147382. PMID 36521179.
  3. ^ a b Shulgin A (2021). The Nature of Drugs. Berkeley, California: Transform Press. pp. 299–300. ISBN 9780999547212.
  4. ^ a b Winter JC (1980-05-01). "Effects of the phenethylamine derivatives, BL-3912, fenfluramine, and Sch-12679, in rats trained with LSD as a discriminative stimulus". Psychopharmacology. 68 (2): 159–162. doi:10.1007/BF00432134. PMID 6776559. S2CID 12221170.
  5. ^ Glennon RA (October 1993). "MDMA-like stimulus effects of alpha-ethyltryptamine and the alpha-ethyl homolog of DOM". Pharmacology, Biochemistry, and Behavior. 46 (2): 459–462. doi:10.1016/0091-3057(93)90379-8. PMID 7903460. S2CID 54356633.
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