2,5-Dimethoxy-4-methylamphetamine

2,5-Dimethoxy-4-methylamphetamine

Names
IUPAC name 1-(2,5-Dimethoxy-4-methylphenyl)-propan-2-amine
Other names 2,5-Dimethoxy-4-methylamphetamine
Identifiers
CAS Number	15588-95-1 N 43061-13-8 (R) N 43061-14-9 (S) N
3D model (Jmol)	Interactive image R-isomer: Interactive image
ChEMBL	ChEMBL317634 Y
ChemSpider	9910656 Y
PubChem	11735949
UNII	UKI9MLD5OI N
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 Y Key: NTJQREUGJKIARY-SECBINFHSA-N Y InChI=1/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-SECBINFHBK
SMILES O(c1cc(c(OC)cc1C[C@H](N)C)C)C R-isomer: N[C@H](C)CC1=C(OC)C=C(C)C(OC)=C1
Properties
Chemical formula	C12H19NO2
Molar mass	209.29 g/mol
Melting point	61 °C (142 °F; 334 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

2,5-Dimethoxy-4-methylamphetamine (DOM; known on the street as STP, standing for "Serenity, Tranquility and Peace") is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I 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. It is generally taken orally.

DOM was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.

In mid-1967, tablets containing 20 mg (later 10 mg) of DOM were widely distributed in the Haight-Ashbury District of San Francisco under the name of STP. This short-lived appearance of DOM on the black market proved disastrous for several reasons. First, the tablets contained an excessively high dose of the chemical. This, combined with DOM’s slow onset of action (which encouraged some users, familiar with drugs that have quicker onsets, such as LSD, to re-dose) and its remarkably long duration, caused many users to panic and sent some to the emergency room. Second, treatment of such overdoses was complicated by the fact that no one at the time knew that the tablets called STP were, in fact, DOM.

Effects of this drug include substantial perceptual changes such as blurred vision, multiple images, vibration of objects, visual alterations, distorted shapes, enhancement of details, slowed passage of time, increased sexual drive and pleasure, and increased contrasts. It may cause mystical experiences and changes in consciousness. It may also cause pupillary dilation and a rise in systolic blood pressure.

DOM is a selective 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor partial agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT_2A receptor. Due to its selectivity, DOM is often used in scientific research when studying the 5-HT₂ receptor subfamily. DOM is a chiral molecule, and R-(−)-DOM is the more active enantiomer, functioning as a potent agonist of the serotonin 5-HT family of receptors; mainly of the 5-HT2 subtype.