2,5-Dimethoxy-4-methylamphetamine

DOM
Clinical data
Other names	2,5-Dimethoxy-4-methylamphetamine; 4-Methyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-methyl-α-methylphenethylamine; Des-oxy-methyl; DOM; DMMTA; α-Me-2C-D; STP; Serenity, Tranquility, and Peace; Super Terrific Psychedelic; Stop The Police; Too Stupid to Puke; K-61,082
Routes of; administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Stimulant; Antidepressant; Psychic energizer
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; UK: Class A; US: Schedule I;
Pharmacokinetic data
Metabolism	Demethylation
Metabolites	• 2-DM-DOM; • 5-DM-DOM; • 2,5-DDM-DOM
Onset of action	0.5–1.5 hours; Peak: 2–6 hours
Duration of action	Low doses: 5–8 hours; Moderate doses: 8–24 hours; High doses: possibly up to 3–4 days
Excretion	5–20% unchanged
Identifiers
	IUPAC name 1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine;
CAS Number	15588-95-1 ; 43061-13-8 ((R)-DOM); 43061-14-9 ((S)-DOM);
PubChem CID	85875;
DrugBank	DB01528;
ChemSpider	77462 ;
UNII	UKI9MLD5OI;
KEGG	C22736;
ChEMBL	ChEMBL8600 ;
CompTox Dashboard (EPA)	DTXSID50860611 ;
Chemical and physical data
Formula	C12H19NO2
Molar mass	209.289 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	61 °C (142 °F)
	SMILES CC1=CC(=C(C=C1OC)CC(C)N)OC;
	InChI InChI=1S/C12H19NO2/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3; Key:NTJQREUGJKIARY-UHFFFAOYSA-N ;
	(verify)

2,5-Dimethoxy-4-methylamphetamine (DOM), also known as STP (standing for "Serenity, Tranquility, and Peace" and other phrases), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It has stimulant and antidepressant-like effects at low doses and hallucinogenic effects at higher doses. The drug can have a very slow onset and long duration, with its duration possibly being up to a few days at high doses. It is usually taken orally.

Side effects of DOM include amphetamine-like effects, among others. The drug acts as a serotonin 5-HT₂ receptor agonist, including of the serotonin 5-HT_2A receptor. Analogues of DOM include mescaline, 2C-D, DOET, DOB, DOI, and Ariadne (4C-D), among others.

DOM was first synthesized and tested by Alexander Shulgin in 1963 and was later further described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). The drug caused a small public health crisis in San Francisco in 1967 when it was introduced as a substitute for LSD, which was due to the tablets containing high doses and causing intense and very long-lived effects. DOM is classified as a Schedule I controlled substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances.