Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2,5-Dimethoxy-4-methylamphetamine: Difference between pages

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| verifiedrevid = 477211718

| ImageFile1 = DOM2DACS.svg

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| PIN = 1-(2,5-Dimethoxy-4-methylphenyl)propan-2-amine

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = UKI9MLD5OI

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = LX3MC6OB9X

| UNII1_Comment = (R)

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 0FRQ2JVN98

| UNII2_Comment = (S)

| CASNo = 15588-95-1

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| CASNo1 = 43061-13-8

| CASNo1_Comment = (R)

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| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 43061-14-9

| CASNo2_Comment = (S)

| KEGG = C22736

| SMILES1 = O(c1cc(c(OC)cc1C[C@H](N)C)C)C

| SMILES2 = N[C@H](C)CC1=C(OC)C=C(C)C(OC)=C1

| SMILES2_Comment = ''R''-[[isomer]]

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| C=12 | H=19 | N=1 | O=2

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| Section4 = {{Chembox Pharmacology

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| Legal_status =

| Legal_AU = S9

| Legal_BR = F2

| Legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| Legal_CA = Schedule I

| Legal_NZ =

| Legal_US = Schedule I

| Legal_UK = Class A

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'''2,5-Dimethoxy-4-methylamphetamine''' ('''DOM'''; known as '''STP''', standing for "'''Serenity, Tranquility and Peace'''") is a [[psychedelic drug|psychedelic]] and a [[substituted amphetamine]]. It was first synthesized by [[Alexander Shulgin]], and later reported in his book ''[[PiHKAL|PiHKAL: A Chemical Love Story]]''. DOM is classified as a [[Controlled Substances Act#Schedule I drugs|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]].<ref>{{cite web|url=http://www.incb.org/documents/Psychotropics/green_lists/Green_list_ENG_2014_85222_GHB.pdf |title=Green List: List of Psychotropic Substances Under International Control |date=August 2003 |edition=23rd |publisher=[[International Narcotics Control Board]] |page=4 |access-date=22 February 2014 |url-status=dead |archive-url=https://web.archive.org/web/20131219071757/http://www.incb.org/documents/Psychotropics/green_lists/Green_list_ENG_2014_85222_GHB.pdf |archive-date=19 December 2013 }}</ref> 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.<ref>{{cite book | last = Shulgin | first = Alexander | title = Pihkal : a chemical love story | publisher = Transform Press | location = Berkeley, CA | year = 1991 | isbn = 978-0-9630096-0-9 | pages = 53–56}}</ref>

In mid-1967, tablets containing 20&nbsp;mg (later 10&nbsp;mg) of STP were widely distributed in the [[Haight-Ashbury|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 experience]]s and changes in [[consciousness]]. It may also cause pupillary dilation and a rise in systolic blood pressure.<ref name="Snyder">{{cite journal|last=Snyder|first=Solomon H.|author2=Louis Faillace|author3=Leo Hollister|name-list-style=amp|date=3 November 1967|title=2,5-Dimethoxy-4-methyl-amphetamine (STP): A New Hallucinogenic Drug|url=https://pubmed.ncbi.nlm.nih.gov/4860952/|format=[[Portable Document Format|PDF]]|journal=[[Science (journal)|Science]]|volume=158|issue=3801|pages=669–670|doi=10.1126/science.158.3801.669|pmid=4860952|bibcode=1967Sci...158..669S|s2cid=24065654}}</ref>

== Pharmacology ==

DOM is a selective [[5-HT2A receptor|5-HT_2A]], [[5-HT2B receptor|5-HT_2B]], and [[5-HT2C receptor|5-HT_2C receptor]] [[partial agonist]]. Its psychedelic effects are mediated by its [[agonist]]ic properties at the 5-HT_2A receptor. Due to its selectivity, DOM is often used in scientific research when studying the [[5-HT2|5-HT₂ receptor]] subfamily. DOM is a [[Chirality (chemistry)|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.<ref>{{cite journal |last=Sanders-Bush |first=E |author2=Burris, KD |author3=Knoth, K |date=September 1988 |title=Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis |journal=[[Journal of Pharmacology and Experimental Therapeutics|The Journal of Pharmacology and Experimental Therapeutics]] |volume=246 |issue=3 |pages=924–928 |pmid=2843634 }}</ref>

=== Analogues and derivatives ===

[[Image:DOM-25-varients.png|280px|thumb|right|Chemical structures of some DOM variants]]

The 2,6-dimethoxy positional isomer of DOM, known as [[Psi-DOM|Ψ-DOM]], is also mentioned in ''PiHKAL'' as being active, as is the alpha-ethyl homologue [[Ariadne (psychedelic)|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.<ref name="pmid12957227">{{cite journal |vauthors=Eckler JR, Chang-Fong J, Rabin RA, Smith C, Teitler M, Glennon RA, Winter JC |title=Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM |journal=Pharmacology Biochemistry and Behavior |volume=75 |issue=4 |pages=845–52 |date=July 2003 |pmid=12957227 |doi= 10.1016/S0091-3057(03)00159-X|s2cid=36463979 }}</ref><ref>{{Cite thesis |title=Towards a Biophysical Basis of Hallucinogen Action |url=https://books.google.com/books?id=sz4zbKBniZQC |last=Braden |first=Michael Robert |date=May 2007 |publisher=Purdue University |access-date=28 February 2012 |oclc=703618147 }}</ref>

==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.<ref name=Snyder />

==Legal status==

===Canada===

Listed as a [[Controlled Drugs and Substances Act#Schedule I|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 [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons standard]].<ref name="Poisons Standard">Poison Standard https://www.comlaw.gov.au/Details/F2015L01534/Html/Text#_Toc420496379 {{webarchive|url=https://web.archive.org/web/20151222222450/https://www.comlaw.gov.au/Details/F2015L01534/Html/Text |date=2015-12-22 }}</ref> 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."<ref name="Poisons Standard" />

===United Kingdom===

DOM is a [[Class A drug]] in the United Kingdom under the [[Misuse of Drugs Act 1971]].

== See also ==

* [[2,5-Dimethoxy-4-Substituted Amphetamine]]s

== References ==

{{Reflist|2}}

==External links==

* [http://www.erowid.org/library/books_online/pihkal/pihkal068.shtml DOM Entry in PiHKAL]

* [http://pihkal.info/read.php?domain=pk&id=68 DOM Entry in PiHKAL • info]

* [http://www.erowid.org/chemicals/dom/dom.shtml Erowid DOM Vault]

{{Hallucinogens}}

{{Serotonergics}}

{{Phenethylamines}}

{{DEFAULTSORT:Dimethoxy-4-methylamphetamine, 2, 5-}}

[[Category:Serotonin receptor agonists]]

[[Category:Substituted amphetamines]]

[[Category:2,5-Dimethoxyphenethylamines]]

[[Category:Designer drugs]]