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 sub ...

. 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 The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as #Amphetamine-type stimulants, amphetamine-type stimulants, barbiturates, benzodiazepines, and Psychedelic drug, psychede ...

. 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 Robert "Tim" Scully (born August 27, 1944) is an American computer engineer, best known in the psychedelic underground for his work in the production of LSD from 1966 to 1969, for which he was indicted in 1973 and convicted in 1974. His best know ...

. 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 se ...

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 Lysergic acid diethylamide (LSD), also known colloquially as acid, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, vi ...

, 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 experience Scholarly approaches to mysticism include typologies of mysticism and the explanation of mystical states. Since the 19th century, mystical experience has evolved as a distinctive concept. It is closely related to "mysticism" but lays sole emphasi ...

s 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-HT_2A, 5-HT_2B, and 5-HT_2C 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 antagonis ...

. 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 ...

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 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 having ...

. 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 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 t ...

, 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.

References

External links

DOM Entry in PiHKAL

DOM Entry in PiHKAL • info

Erowid DOM Vault
{{DEFAULTSORT:Dimethoxy-4-methylamphetamine, 2, 5- Serotonin receptor agonists Substituted amphetamines 2,5-Dimethoxyphenethylamines Designer drugs