STP was first synthesized and tested in 1963 by
Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.[3]
In mid-1967, tablets containing 20 mg (later 10 mg) of STP were widely distributed in the
Haight-Ashbury District of
San Francisco under the name of STP, having been manufactured by underground chemists
Owsley Stanley and
Tim Scully. This short-lived appearance of STP 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
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.[4]
Pharmacology
DOM is a selective
5-HT2A,
5-HT2B, and
5-HT2C receptorpartial agonist. Its psychedelic effects are mediated by its
agonistic properties at the 5-HT2A 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.[5]
Analogues and derivatives
The 2,6-dimethoxy positional isomer of DOM, known as
Ψ-DOM, is also mentioned in PiHKAL as being active, as is the alpha-ethyl homologue
Ariadne. Analogues where the methoxy groups at the 2,5- positions of the aromatic ring have been altered have also been synthesised and tested as part of an effort to identify the binding mode of DOM at the 5-HT2A receptor. Both the 2- and 5- O-desmethyl derivatives 2-DM-DOM and 5-DM-DOM, and the 2- and 5- ethyl analogues 2-Et-DOM and 5-Et-DOM have been tested, but in all cases were significantly less potent than the corresponding methoxy compound, showing the importance of the oxygen lone pairs in 5-HT2A binding.[6][7]
Toxicity
Very little is known about the toxicity of DOM. According to
Alexander Shulgin, the effects of DOM typically last 14 to 20 hours, though other clinical trials indicate a duration of 7 to 8 hours.[4]
Legal status
Canada
Listed as a
Schedule 1, as it is an analogue of amphetamine.
United States
DOM is Schedule I in the United States. This means it is illegal to manufacture, buy, possess, or distribute (make, trade, own or give) without a DEA license.
Australia
DOM is schedule 9 under the Australia
Poisons standard.[8] A schedule 9 substance is a "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities."[8]
^Sanders-Bush, E; Burris, KD; Knoth, K (September 1988). "Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis". The Journal of Pharmacology and Experimental Therapeutics. 246 (3): 924–928.
PMID2843634.
^Eckler JR, Chang-Fong J, Rabin RA, Smith C, Teitler M, Glennon RA, Winter JC (July 2003). "Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM". Pharmacology Biochemistry and Behavior. 75 (4): 845–52.
doi:
10.1016/S0091-3057(03)00159-X.
PMID12957227.
S2CID36463979.