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{{SubstanceBox/DOM}} | {{SubstanceBox/DOM}} | ||
'''2,5-Dimethoxy-4-methylamphetamine''' (also known as '''DOM''' and '''STP''' or '''"Serenity, Tranquility and Peace"''') is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::amphetamine]] class. DOM is a member of the [[DOx]] family of compounds which are known for their high potency, long duration, and mixture of [[psychedelic]] and [[stimulant]] effects. It produces its effects by acting on [[serotonin]] receptors in the brain. | '''2,5-Dimethoxy-4-methylamphetamine''' (also known as '''DOM''' and '''STP''' or '''"Serenity, Tranquility and Peace"''') is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::Substituted amphetamine|amphetamine]] class. DOM is a member of the [[DOx]] family of compounds which are known for their high potency, long duration, and mixture of [[psychedelic]] and [[stimulant]] effects. It produces its effects by acting on [[serotonin]] receptors in the brain. | ||
DOM was first synthesized and tested in 1963 by [[Alexander Shulgin]].<ref name="DOM"> | DOM was first synthesized and tested in 1963 by [[Alexander Shulgin]].<ref name="DOM">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|pages=53-56}}</ref> It attained some popularity during the summer of 1967 under the name "STP" ("Serenity, Tranquility, and Peace"),<ref>{{cite journal | vauthors=((Berkeley, B.)) | journal=Independent Voices | title=STP’s faster, here’s why | pages=3–5 | date=16 April 1967 | url=http://voices.revealdigital.com/cgi-bin/independentvoices?a=d&d=BFBJFGD19670616.1.3}}</ref> but its use was short-lived due to its side effects. In 1991, the synthesis and pharmacology of DOM was published in Shulgin's book ''[[PiHKAL]]'' ("Phenethylamines I Have Known And Loved").<ref name="PiHKAL">{{Citation | title=Erowid Online Books : “PIHKAL” - The Chemical Story | url=https://www.erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref>. | ||
Over the years, DOM has gained a reputation for being a highly dose-sensitive psychedelic that is often sold on blotting paper and known for its strong visuals, body load and neutral, analytical headspace. Many reports also indicate that the effects of this chemical may be overly difficult to use for those who are not already experienced with psychedelics. | Over the years, DOM has gained a reputation for being a highly dose-sensitive psychedelic that is often sold on blotting paper and known for its strong visuals, body load and neutral, analytical headspace. Many reports also indicate that the effects of this chemical may be overly difficult to use for those who are not already experienced with psychedelics. | ||
==History and culture== | ==History and culture== | ||
DOM was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.<ref name="DOM" /> 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]]. | DOM was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.<ref name="DOM" /> 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}} | 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}} | ||
==Chemistry== | ==Chemistry== | ||
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 (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOM contains methoxy functional groups (OCH<sub>3</sub>) attached to carbons R<sub>2</sub> and R<sub>5</sub> and a methyl group attached to carbon R<sub>4</sub> of the phenyl ring. | 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 (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOM contains methoxy functional groups (OCH<sub>3</sub>) attached to carbons R<sub>2</sub> and R<sub>5</sub> and a methyl group attached to carbon R<sub>4</sub> of the phenyl ring. DOM is the amphetamine analogue of the phenethylamine [[2C-D]].<ref name=":0">{{Citation | title=#62 DOB PiHKAL | url=http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=62}}</ref><ref>{{Citation | title=#68 DOM PiHKAL | url=http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=68}}</ref> | ||
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 <abbr>LD50</abbr> 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.<ref name=":0" /> | |||
==Pharmacology== | ==Pharmacology== | ||
{{Further|Serotonergic psychedelic}} | {{Further|Serotonergic psychedelic}} | ||
DOM is a selective [[agonist|partial agonist]] at the [[Serotonin#The 5-HT System|5-HT<sub>2</sub> receptor]] family. Its psychedelic effects are mediated by its [[agonist]]ic properties at the 5-HT<sub>2A</sub> and 5-HT<sub>2B</sub> receptors, but less so on the 5-HT<sub>2C</sub> receptor. Due to its selectivity, DOM is often used in scientific research when studying the [[Serotonin#The 5-HT System|5-HT<sub>2</sub> receptor]] subfamily. | DOM is a selective [[agonist|partial agonist]] at the [[Serotonin#The 5-HT System|5-HT<sub>2</sub> receptor]] family. Its psychedelic effects are mediated by its [[agonist]]ic properties at the 5-HT<sub>2A</sub> and 5-HT<sub>2B</sub> receptors, but less so on the 5-HT<sub>2C</sub> receptor. Due to its selectivity, DOM is often used in scientific research when studying the [[Serotonin#The 5-HT System|5-HT<sub>2</sub> receptor]] subfamily. DOM is a [[Chirality|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-HT<sub>2</sub> subtype).<ref>{{cite journal | vauthors=((Sanders-Bush, E.)), ((Burris, K. D.)), ((Knoth, K.)) | journal=The Journal of Pharmacology and Experimental Therapeutics | title=Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis | volume=246 | issue=3 | pages=924–928 | date= September 1988 | issn=0022-3565}}</ref> However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive. | ||
DOM is | 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<sub>2A</sub> 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<sub>2A</sub> binding.<ref>{{cite journal | vauthors=((Eckler, J. R.)), ((Chang-Fong, J.)), ((Rabin, R. A.)), ((Smith, C.)), ((Teitler, M.)), ((Glennon, R. A.)), ((Winter, J. C.)) | journal=Pharmacology Biochemistry and Behavior | title=Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM | volume=75 | issue=4 | pages=845–852 | date= July 2003 | url=https://linkinghub.elsevier.com/retrieve/pii/S009130570300159X | issn=00913057 | doi=10.1016/S0091-3057(03)00159-X}}</ref> | ||
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.<ref name=":0" /> | |||
==Subjective effects== | ==Subjective effects== | ||
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{{#ask: [[Category:DOM]][[Category:Experience]]|format=ul|Columns=1}} | {{#ask: [[Category:DOM]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://www.erowid.org/experiences/subs/exp_DOM.shtml Erowid Experience Vaults: DOM] | |||
*[https://www.erowid.org/experiences/subs/exp_DOM.shtml Erowid Experience Vaults: DOM] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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DOM is [[Addiction potential::not habit-forming]] and the desire to use it can decrease with use. It is most often self-regulating. | DOM is [[Addiction potential::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 | Tolerance to the effects of DOM is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). DOM presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of DOM all psychedelics will have a reduced effect. | ||
===Overdose=== | ===Overdose=== | ||
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{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
*'''[[Tramadol]]''' - Tramadol lowers the seizure threshold<ref>Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., | *'''[[DangerousInteraction::Lithium]]''':<ref>{{Citation | vauthors=((Nayak, S.)), ((Gukasyan, N.)), ((Barrett, F. S.)), ((Erowid, E.)), ((Erowid, F.)), ((Griffiths, R. R.)) | year=2021 | title=Classic psychedelic coadministration with lithium, but not lamotrigine, is associated with seizures: an analysis of online psychedelic experience reports | publisher=PsyArXiv | url=https://osf.io/r726d}}</ref> 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]].<ref>{{cite web|url=https://erowid.org/experiences/exp.php?ID=83935|title=A Nice Little Trip to the Hospital: Lithium & LSD|author=<nowiki>"wanderlei"</nowiki>|publisher=Erowid|publication-date=October 3, 2010|access-date=January 7, 2020|id=ExpID: 83935|work=Erowid Experience Vaults}}</ref><ref>{{cite web|url=https://erowid.org/experiences/exp.php?ID=75153|title=Having a Seizure and Passing Out: Lithium & LSD|author=<nowiki>"MissDja1a"</nowiki>|publisher=Erowid|publication-date=December 16, 2008|access-date=January 7, 2020|id=ExpID: 75153|work=Erowid Experience Vaults}}</ref><ref>{{cite web|url=https://www.reddit.com/r/Psychonaut/comments/17uspp/please_read_a_cautionary_tale_concerning_lsd|title=Please Read: a cautionary tale concerning LSD|author=<nowiki>"throwaway_naut"</nowiki>|publisher=Reddit|work=r/Psychonaut|year=2014|access-date=January 7, 2020}}</ref> As a result, this combination should be '''strictly avoided'''. | ||
*'''[[Stimulants]]''' - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable [[anxiety]], [[Panic attacks|panic]], [[thought loops]] and [[paranoia]]. This interaction may cause elevated risk of psychosis | *'''[[[[UnsafeInteraction::Tramadol|Tramadol]]]]''' - Tramadol lowers the seizure threshold<ref>{{cite journal | vauthors=((Talaie, H.)), ((Panahandeh, R.)), ((Fayaznouri, M. R.)), ((Asadi, Z.)), ((Abdollahi, M.)) | journal=Journal of Medical Toxicology | title=Dose-independent occurrence of seizure with tramadol | volume=5 | issue=2 | pages=63–67 | date= June 2009 | url=http://link.springer.com/10.1007/BF03161089 | issn=1556-9039 | doi=10.1007/BF03161089}}</ref> and [[psychedelics]] may act as triggers for seizures, particularly in those who are predisposed to them.{{citation needed}} | ||
*'''[[[[UncertainInteraction::Stimulants|Stimulants]]]]''' - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable [[anxiety]], [[Panic attacks|panic]], [[thought loops]] and [[paranoia]]. This interaction may cause elevated risk of psychosis.{{citation needed}} | |||
==Legal status== | ==Legal status== | ||
*'''Austria | |||
*'''Brazil | Internationally, mescaline is part of the the Convention on Psychotropic Substances of 1971 as a Schedule I substance.<ref>{{cite web|url=http://www.emcdda.europa.eu/system/files/attachments/10451/convention_1971_en.pdf|title=CONVENTION ON PSYCHOTROPIC SUBSTANCES 1971|publisher=United Nations|access-date=December 10, 2019}}</ref> | ||
*'''Belgium:''' DOM is a Schedule I drug.{{ | |||
*''' | *'''Australia''': Australia has a blanket ban over all substituted phenethylamines including the entire [[DOx]] family.<ref>New Psychoactive Substances (National Drug and Alcohol Research Centre 2014) | https://comorbidity.edu.au/sites/default/files/cre/page/New%20Psychoactive%20Substances.pdf</ref> | ||
*'''Latvia | *'''Austria''': DOM is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}} | ||
*'''New Zealand | *'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344 as "STP".<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref> | ||
*'''Switzerland | *'''Belgium''': DOM is a Schedule I drug.<ref>https://www.wiv-isp.be/epidemio/epien/birn/EWS03.pdf</ref> | ||
*'''United Kingdom | *'''Canada''': DOM is a Schedule I drug.<ref>{{Citation | vauthors=((Branch, L. S.)) | year=2022 | title=Consolidated federal laws of Canada, Controlled Drugs and Substances Act | url=https://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-13.html}}</ref> | ||
*'''United States | *'''Germany''': DOM is controlled under Anlage I BtMG (Narcotics Act, Schedule I), former: Opiumgesetz (Opium Act) as of April 15, 1971.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?start=//*%5B@attr_id=%27bgbl171s0315.pdf%27%5D#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl171s0315.pdf%27%5D__1576103284216|title=Fünfte Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 11, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> | ||
*'''Latvia''': DOM is a Schedule I controlled substance.<ref>{{Citation | title=Zaudējis spēku - Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem | url=https://likumi.lv/doc.php?id=121086}}</ref> | |||
*'''New Zealand''': DOM is a Class A drug.{{citation needed}} | |||
*'''Switzerland''': DOM is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | |||
*'''United Kingdom''': DOM is a Class A drug.<ref>{{Citation | title=Misuse of Drugs Act 1971 | url=https://www.legislation.gov.uk/ukpga/1971/38/schedule/2#commentary-M_F_83d9b65b-d638-43b1-ea64-c129d6f1ef0a}}</ref> | |||
*'''United States''': DOM is a Schedule I drug.{{citation needed}} | |||
*'''Czech Republic''': DOM is a Schedule I drug.<ref>{{Citation | title=463/2013 Sb. Nařízení vlády o seznamech návykových látek | url=https://www.zakonyprolidi.cz/cs/2013-463}}</ref> | |||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Psychedelics]] | *[[Psychedelics]] | ||
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==External links== | ==External links== | ||
*[http://en.wikipedia.org/wiki/2,5-Dimethoxy-4-methylamphetamine DOM (Wikipedia)] | *[http://en.wikipedia.org/wiki/2,5-Dimethoxy-4-methylamphetamine DOM (Wikipedia)] | ||
*[https://www.erowid.org/chemicals/dom/dom.shtml DOM (Erowid Vault)] | *[https://www.erowid.org/chemicals/dom/dom.shtml DOM (Erowid Vault)] | ||
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===Discussion=== | ===Discussion=== | ||
*[http://www.bluelight.org/vb/threads/291980-The-Big-amp-Dandy-DOM-Thread The Big & Dandy DOM Thread (Bluelight)] | *[http://www.bluelight.org/vb/threads/291980-The-Big-amp-Dandy-DOM-Thread The Big & Dandy DOM Thread (Bluelight)] | ||
==References== | ==References== | ||
<references/> | <references /> | ||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Psychedelic]] | [[Category:Psychedelic]] | ||
[[Category:DOx]] | |||
{{#set:Featured=true | {{#set:Featured=true | ||
|RN= | |RN= | ||