5C-D

5C-D, also known as 4-methyl-2,5-dimethoxy-α-propylphenethylamine, is a putatively non-hallucinogenic serotonin 5-HT₂ receptor agonist of the phenethylamine and α-propylphenethylamine families related to the 4C drug Ariadne (4C-D).^[1][2]

5C-D

Clinical data
Other names	4-Methyl-2,5-dimethoxy-α-propylphenethylamine; 2,5-Dimethoxy-4-methyl-α-propylphenethylamine; α-Propyl-Ariadne; 5C-DOM; α-Propyl-2C-D
Drug class	Serotonin 5-HT2 receptor agonist
ATC code	None
Identifiers
IUPAC name 1-(2,5-dimethoxy-4-methylphenyl)pentan-2-amine
PubChem CID	171417407
Chemical and physical data
Formula	C14H23NO2
Molar mass	237.343 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCC(CC1=C(C=C(C(=C1)OC)C)OC)N
InChI InChI=1S/C14H23NO2/c1-5-6-12(15)8-11-9-13(16-3)10(2)7-14(11)17-4/h7,9,12H,5-6,8,15H2,1-4H3 Key:VZEDHPXICDLLDV-UHFFFAOYSA-N

At the serotonin 5-HT_2A receptor, 5C-D is a potent and higher-efficacy partial agonist, with an EC₅₀Tooltip half-maximal effective concentration of 291 nM and an E_maxTooltip maximal efficacy of 69%.^[1][2] It is about half as potent as Ariadne as a serotonin 5-HT_2A receptor agonist and has about 15% lower efficacy in activating the receptor in comparison.^[1][2] 5C-D has also been shown to be a serotonin 5-HT_2B receptor agonist.^[2] In contrast to Ariadne and serotonergic psychedelics, 5C-D does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[2]

5C-D was first described in the scientific literature by Michael Cunningham and colleagues by 2023.^[2] It was synthesized and assessed during structure–activity relationship (SAR) studies of Ariadne.^[1][2]

See also

• Substituted methoxyphenethylamine
• 4C and Ariadne (4C-D)