2C-D

2C-D
Clinical data
Other names	4-Methyl-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-methyl-phenethylamine; 2C-M; 2C-DOM; LE-25; LE25; DMMPEA; DMM-PEA
Routes of; administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Stimulant; Cognitive enhancer
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule III; DE: Anlage I (Authorized scientific use only); US: Schedule I;
Pharmacokinetic data
Onset of action	20–30 minutes
Duration of action	4–6 hours
Identifiers
	IUPAC name 2-(2,5-dimethoxy-4-methylphenyl)ethan-1-amine;
CAS Number	24333-19-5 ;
PubChem CID	135740;
ChemSpider	119559 ;
UNII	7J43GY6ONS;
ChEMBL	ChEMBL124049 ;
CompTox Dashboard (EPA)	DTXSID10179074 ;
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	213 to 214 °C (415 to 417 °F) (hydrochloride)
	SMILES O(c1cc(c(OC)cc1CCN)C)C;
	InChI InChI=1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3 ; Key:UNQQFDCVEMVQHM-UHFFFAOYSA-N ;
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2C-D, also known as 4-methyl-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It has an unusually wide and gradual dose range and at low doses produces claimed cognitive enhancer-like effects, mild stimulant effects, and mild perceptual effects, whereas at high doses, it produces robust psychedelic effects. The drug is taken orally.

It acts as an agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A receptor. The drug is structurally related to other psychedelic and related phenethylamines such as its higher homologues DOM and Ariadne (4C-D) and other 2C psychedelics like 2C-B and 2C-E.

2C-D was first described in the literature by Beng T. Ho and colleagues in 1970. Its properties and effects in humans were described by Alexander Shulgin and colleagues in 1975. The drug was extensively studied by Hanscarl Leuner under the names DMM-PEA and LE-25 in psychedelic-assisted psychotherapy in Germany in the 1970s and 1980s. It was also informally studied by Darrell Lemaire as a potential "smart drug" in the 1970s and 1980s. 2C-D was first encountered as a novel designer drug by 2005. It became a controlled substance in the United States in 2012.