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
Drug class	Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; UK: Class A; US: Schedule I;
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	11735949;
ChemSpider	9910656 ;
UNII	UKI9MLD5OI;
KEGG	C22736;
ChEMBL	ChEMBL317634 ;
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 O(c1cc(c(OC)cc1C[C@H](N)C)C)C;
	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/t9-/m1/s1; Key:NTJQREUGJKIARY-SECBINFHSA-N ;
	(verify)

2,5-Dimethoxy-4-methylamphetamine (DOM), also known as STP (standing for "Serenity, Tranquility, and Peace" and/or other phrases), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.^[4]^[5]^[1]^[6]^[7] It is generally taken orally.^[5]^[1]^[6]

DOM was first synthesized by Alexander Shulgin, and later described in his book PiHKAL: A Chemical Love Story (1991).^[1] It is classified as a Schedule I controlled substance in the United States, and is similarly controlled in other parts of the world.^[1] Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances.^[8]

^ ^a ^b ^c ^d ^e Baggott MJ (1 October 2023). "Learning about STP: A Forgotten Psychedelic from the Summer of Love" (PDF). History of Pharmacy and Pharmaceuticals. 65 (1): 93–116. doi:10.3368/hopp.65.1.93. ISSN 2694-3034. Retrieved 26 January 2025.
^ Trout K, Daley PF (December 2024). "The origin of 2,5-dimethoxy-4-methylamphetamine (DOM, STP)" (PDF). Drug Test Anal. 16 (12): 1496–1508. doi:10.1002/dta.3667. PMID 38419183.
^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ Shulgin A, Manning T, Daley PF (2011). "#60. DOM". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 118–129. ISBN 978-0-9630096-3-0. OCLC 709667010.
^ ^a ^b Alexander T. Shulgin; Ann Shulgin (1991). "#68 DOM; STP; 2,5-DIMETHOXY-4-METHYLAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. pp. 637–642. ISBN 978-0-9630096-0-9. OCLC 25627628.
^ ^a ^b Wills B, Erickson T (9 March 2012). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". In Barceloux DG (ed.). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Wiley. pp. 156–192. doi:10.1002/9781118105955.ch10. ISBN 978-0-471-72760-6.
^ Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.
^ "Green List: List of Psychotropic Substances Under International Control" (PDF) (23rd ed.). International Narcotics Control Board. August 2003. p. 4. Archived from the original (PDF) on 19 December 2013. Retrieved 22 February 2014.

[Baggott2023-1] Baggott MJ (1 October 2023). "Learning about STP: A Forgotten Psychedelic from the Summer of Love" (PDF). History of Pharmacy and Pharmaceuticals. 65 (1): 93–116. doi:10.3368/hopp.65.1.93. ISSN 2694-3034. Retrieved 26 January 2025.

[TroutDaley2024-2] Trout K, Daley PF (December 2024). "The origin of 2,5-dimethoxy-4-methylamphetamine (DOM, STP)" (PDF). Drug Test Anal. 16 (12): 1496–1508. doi:10.1002/dta.3667. PMID 38419183.

[3] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[ShulginManningDaley2011-4] Shulgin A, Manning T, Daley PF (2011). "#60. DOM". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 118–129. ISBN 978-0-9630096-3-0. OCLC 709667010.

[PiHKAL1991-5] Alexander T. Shulgin; Ann Shulgin (1991). "#68 DOM; STP; 2,5-DIMETHOXY-4-METHYLAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. pp. 637–642. ISBN 978-0-9630096-0-9. OCLC 25627628.

[WillsErickson2012-6] Wills B, Erickson T (9 March 2012). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". In Barceloux DG (ed.). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Wiley. pp. 156–192. doi:10.1002/9781118105955.ch10. ISBN 978-0-471-72760-6.

[Shulgin1978-7] Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.

[INCB2003-8] "Green List: List of Psychotropic Substances Under International Control" (PDF) (23rd ed.). International Narcotics Control Board. August 2003. p. 4. Archived from the original (PDF) on 19 December 2013. Retrieved 22 February 2014.

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