DOM

DOM was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.^[1] DOM is part of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important phenethylamine compounds, all of which except mescaline he developed and synthesized himself. They are found within the first book of PiHKAL and are as follows: Mescaline, DOM, 2C-B, 2C-E, 2C-T-2 and 2C-T-7.

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" (short for "Serenity, Tranquility, and Peace").^{[citation needed]} 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 substances 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 it was unknown at the time that the tablets called "STP" were DOM.^{[citation needed]}

DOM, or 4-methyl-2,5-dimethoxyamphetamine, is a molecule of the substituted amphetamine class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH₂) group through an ethyl chain and a methyl group bound to the alpha carbon R_α. DOM contains methoxy functional groups (OCH₃) attached to carbons R₂ and R₅ and a methyl group attached to carbon R₄ of the phenyl ring. DOM is the amphetamine analogue of the phenethylamine 2C-D.^[4][5]

This is one of the last of the experimental compounds within the phenethylamine family on which any animal toxicity studies were performed prior to human studies. The LD50 of DOM is between 100 - 125 mg/kg for a mouse. An effective dose in a human of 2 mg (for an 80 kg man) is equivalent to 25 μg/kg.

As with DOI, the presence of a heavy atom, the bromine atom, in DOB makes the radioactive isotope labelled material a powerful research tool.^[4]

DOM is a selective partial agonist at the 5-HT₂ receptor family. Its psychedelic effects are mediated by its agonistic properties at the 5-HT_2A and 5-HT_2B receptors, but less so on the 5-HT_2C 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 family of receptors (mainly of the 5-HT₂ subtype).^[6] However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

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-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.^[7]

There is a strong implication that some metabolic conversion occurs in the lung, and it is only after this that the truly active metabolite is available for central action. This is consistent with the relatively slow onset of effect, and the very long duration of action.^[4]

User reports suggest that DOM is relatively clear-headed and absent of side-effects in comparison to DOC or DOB. Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

• Erowid Experience Vaults: DOM

The toxicity and long-term health effects of recreational DOM use do not seem to have been studied in any scientific context and the exact toxic dose is unknown.

Anecdotal evidence suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is strongly recommended that one use harm reduction practices when using this substance.

Tolerance and addiction potential

DOM is not habit-forming and the desire to use it can decrease with use. It is most often self-regulating.

Tolerance to the effects of DOM is built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). DOM presents cross-tolerance with all psychedelics, meaning that after the consumption of DOM all psychedelics will have a reduced effect.

Overdose

The risk of a DOx overdose is present starting in or past the heavy dose range with sensitive people, or when a DOx is mixed with other substances, particularly stimulants or MAOIs. Non-oral routes also seem to exhibit a higher chance of overdosing, perhaps owing to differences in bioavailability, potency and unpredictability of dosage and effects. The effects of a DOx overdose typically include bizarre, delusional and sometimes violent behavior, amnesia, numbness, confusion and anxiety. The user may not be able to communicate and can be severely agitated. At appropriately high doses, more serious side effects such as psychosis, panic attacks and seizures which in turn further affect a dangerously elevated heart rate, blood pressure and vasoconstriction may occur.^{[citation needed]} Severe vasoconstriction typically develops to its peak several hours into the intoxication and may require medical assistance if blood flow is significantly cut off for extended periods of time.

In the event of an overdose, benzodiazepines or antipsychotics can be administered to mitigate the hyperagitative effects.^{[citation needed]} A powerful vasodilator may also need to be administered to prevent a hypertensive emergency, or in more serious cases, necrosis, organ failure and death from the resulting hypoxia.^{[citation needed]} As a result, emergency medical services should always be sought in the event of a DOx overdose.

Dangerous interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

• Lithium:^[8] Lithium is commonly prescribed in the treatment of bipolar disorder; however, there is a large body of anecdotal evidence that suggests taking it with psychedelics can significantly increase the risk of psychosis and seizures.^[9][10][11] As a result, this combination should be strictly avoided.
• Tramadol - Tramadol lowers the seizure threshold^[12] and psychedelics may act as triggers for seizures, particularly in those who are predisposed to them.^{[citation needed]}
• Stimulants - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable anxiety, panic, thought loops and paranoia. This interaction may cause elevated risk of psychosis.^{[citation needed]}

Internationally, mescaline is part of the the Convention on Psychotropic Substances of 1971 as a Schedule I substance.^[13]

• Australia: Australia has a blanket ban over all substituted phenethylamines including the entire DOx family.^[14]
• Austria: DOM is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).^{[citation needed]}
• Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344 as "STP".^[15]
• Belgium: DOM is a Schedule I drug.^[16]
• Canada: DOM is a Schedule I drug.^[17]
• Germany: DOM is controlled under Anlage I BtMG (Narcotics Act, Schedule I), former: Opiumgesetz (Opium Act) as of April 15, 1971.^[18][19] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.^[20]
• Latvia: DOM is a Schedule I controlled substance.^[21]
• New Zealand: DOM is a Class A drug.^{[citation needed]}
• Switzerland: DOM is a controlled substance specifically named under Verzeichnis D.^[22]
• United Kingdom: DOM is a Class A drug.^[23]
• United States: DOM is a Schedule I drug.^{[citation needed]}
• Czech Republic: DOM is a Schedule I drug.^[24]

• Responsible use
• Psychedelics
• Phenethylamines
• DOx
• DOC
• DOI
• 2C-D

• DOM (Wikipedia)
• DOM (Erowid Vault)
• DOM (PiHKAL / Isomer Design)

Discussion

• The Big & Dandy DOM Thread (Bluelight)