Ariadne (drug)

Ariadne
Clinical data
Trade names	Dimoxamine (tentative)
Other names	ARIADNE; 4-Methyl-2,5-dimethoxy-α-ethylphenethylamine; 2,5-Dimethoxy-4-methyl-α-ethylphenethylamine; 4C-D; 4C-DOM; "Four-carbon DOM"; α-Et-2C-D; α-Ethyl-2C-D; BL-3912; BL3912; Dimoxamine
Drug class	Serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor agonist; Non-hallucinogenic serotonin 5-HT2A receptor agonist
Legal status
Legal status	?;
Identifiers
	IUPAC name 1-(2,5-dimethoxy-4-methylphenyl)butan-2-amine;
CAS Number	52842-58-7 ; 52842-59-8 ((R)-isomer);
PubChem CID	169886;
ChemSpider	148565 ;
UNII	09426ZTO78;
CompTox Dashboard (EPA)	DTXSID501343240 DTXSID30967314, DTXSID501343240 ;
Chemical and physical data
Formula	C13H21NO2
Molar mass	223.316 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1cc(c(OC)cc1C[C@H](N)CC)C)C;
	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 ; Key:MLYCFWZIAJAIGW-UHFFFAOYSA-N ;
	(verify)

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 little-known psychoactive drug of the phenethylamine, phenylisobutylamine, and 4C families. It is a homologue of the psychedelics 2C-D and DOM.

The drug is a serotonin receptor agonist, including of the serotonin 5-HT_2A receptor. However, it is non-hallucinogenic in animals and humans, although it still has some psychoactive effects. It may be non-hallucinogenic due to lower-efficacy partial agonism of the serotonin 5-HT_2A receptor.

Ariadne was developed by Alexander Shulgin. It was studied at Bristol Laboratories as an antidepressant and for various other uses but was never marketed. There has been renewed interest in Ariadne in the 2020s owing to increased interest in psychedelics for treatment of psychiatric disorders.