DME (drug)

DME
Clinical data
Other names	3,4-Dimethoxy-β-hydroxyphenethylamine; β-Hydroxy-3,4-dimethoxyphenethylamine; β-Hydroxy-3,4-DMPEA; β-OH-3,4-DMPEA; β-Hydroxy-DMPEA; β-OH-DMPEA
Routes of; administration	Oral
Drug class	Psychoactive drug
ATC code	None;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name 2-amino-1-(3,4-dimethoxyphenyl)ethan-1-ol;
CAS Number	6924-15-8 ;
PubChem CID	3863978;
ChemSpider	3088871 ;
UNII	F9TYB6AM4W;
CompTox Dashboard (EPA)	DTXSID50512380 ;
Chemical and physical data
Formula	C10H15NO3
Molar mass	197.234 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(ccc1OC)C(O)CN;
	InChI InChI=1S/C10H15NO3/c1-13-9-4-3-7(8(12)6-11)5-10(9)14-2/h3-5,8,12H,6,11H2,1-2H3 ; Key:WIUFFBGZBFVVDL-UHFFFAOYSA-N ;
	(verify)

DME, also known as 3,4-dimethoxy-β-hydroxyphenethylamine or as β-hydroxy-3,4-DMPEA, is a psychoactive drug of the phenethylamine and BOx families.^[1] It is the β-hydroxy derivative of 3,4-dimethoxyphenethylamine (3,4-DMPEA or DMPEA), which is an analogue of mescaline (3,4,5-TMPEA or TMPEA).^[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DME's dose as greater than 115 mg orally and its duration as unknown.^[1] At a dose of 115 mg orally, its effects included faint nausea and possible alertness, but described as "substantially no effects".^[1]

Chemistry

Synthesis

The chemical synthesis of DME has been described.^[1]

Analogues

Analogues of DME (β-hydroxy-3,4-DMPEA) include BOH (β-methoxy-MDPEA) and BOM (β-methoxymescaline; β-methoxy-3,4,5-TMPEA), among others.^[1]

History

DME was first described in the scientific literature by Alexander Shulgin and colleagues in 1969.^[2] It was subsequently described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Society and culture

Legal status

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.^[3]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. DME Entry
^ Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure--activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. doi:10.1038/221537a0. PMID 5789297.
^ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.

External links

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. DME Entry

[ShulginSargentNaranjo1969-2] Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure--activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. doi:10.1038/221537a0. PMID 5789297.

[3] "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.

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