2,5-Dimethoxy-4-methylamphetamine (DOM; known as STP, standing for "Serenity, Tranquility and Peace") is a
psychedelic and a
substituted amphetamine
Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with s ...
. 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 Schedule 1 may refer to:
* Schedule I Controlled Substances within the US Controlled Substances Act
* Schedule I Controlled Drugs and Substances within the Canadian Controlled Drugs and Substances Act
* Schedule I Psychotropic Substances within th ...
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
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamine-type stimulants, barbiturates, benzodiazepines, and psychedelics signed in Vienna, Austria on 21 Februar ...
. It is generally taken orally.
History
STP 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 STP were widely distributed in the
Haight-Ashbury District of
San Francisco
San Francisco (; Spanish language, Spanish for "Francis of Assisi, Saint Francis"), officially the City and County of San Francisco, is the commercial, financial, and cultural center of Northern California. The city proper is the List of Ca ...
under the name of STP, having been manufactured by underground chemists
Owsley Stanley
Augustus Owsley Stanley III (January 19, 1935 – March 12, 2011) was an American-Australian audio engineer and clandestine chemist. He was a key figure in the San Francisco Bay Area hippie movement during the 1960s and played a pivotal role ...
and
Tim Scully. This short-lived appearance of STP on the
black market
A black market, underground economy, or shadow economy is a clandestine market or series of transactions that has some aspect of illegality or is characterized by noncompliance with an institutional set of rules. If the rule defines the ...
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
Blurred vision is an ocular symptom where vision becomes less precise and there is added difficulty to resolve fine details.
Temporary blurred vision may involve dry eyes, eye infections, alcohol poisoning, hypoglycemia, or low blood pressu ...
, 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
Consciousness, at its simplest, is sentience and awareness of internal and external existence. However, the lack of definitions has led to millennia of analyses, explanations and debates by philosophers, theologians, linguisticians, and scien ...
. It may also cause pupillary dilation and a rise in systolic blood pressure.
Pharmacology
DOM is a selective
5-HT2A,
5-HT2B, and
5-HT2C receptor partial agonist
In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonist ...
. Its psychedelic effects are mediated by its
agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...
ic 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
Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object.
An object or a system is ''chiral'' if it is distinguishable from i ...
molecule, and ''R''-(−)-DOM is the more active
enantiomer
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
, functioning as a potent agonist of the serotonin
5-HT
Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vas ...
family of receptors; mainly of the
5-HT2
The 5-HT2 receptors are a subfamily of 5-HT receptors that bind the endogenous neurotransmitter serotonin (5-hydroxytryptamine, 5-HT). The 5-HT2 subfamily consists of three G protein-coupled receptors (GPCRs) which are coupled to Gq/G11 and media ...
subtype.
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
Ariadne (; grc-gre, Ἀριάδνη; la, Ariadne) was a Cretan princess in Greek mythology. She was mostly associated with mazes and labyrinths because of her involvement in the myths of the Minotaur and Theseus. She is best known for havin ...
. 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-HT
2A 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-HT
2A binding.
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.
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.
[Poison Standard https://www.comlaw.gov.au/Details/F2015L01534/Html/Text#_Toc420496379 ] 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."
United Kingdom
DOM is a
Class A drug
These drugs are known in the UK as ''controlled drugs'', because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other dru ...
in the United Kingdom under the
Misuse of Drugs Act 1971
The Misuse of Drugs Act 1971 is an Act of the Parliament of the United Kingdom. It represents action in line with treaty commitments under the Single Convention on Narcotic Drugs, the Convention on Psychotropic Substances, and the United Natio ...
.
See also
*
2,5-Dimethoxy-4-Substituted Amphetamine
4-Substituted-2,5-dimethoxyamphetamines (DO''x'') is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of ...
s
References
External links
DOM Entry in PiHKALDOM Entry in PiHKAL • infoErowid DOM Vault
{{DEFAULTSORT:Dimethoxy-4-methylamphetamine, 2, 5-
Serotonin receptor agonists
Substituted amphetamines
2,5-Dimethoxyphenethylamines
Designer drugs