PsychonautWiki Archive

DOM: Difference between revisions

← Older edit
>Apatheist
m Grammatics
>Larnaca
Undo revision 166772 by Blackhole (talk)
 
(4 intermediate revisions by 3 users not shown)
Line 4: Line 4:
'''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.
'''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">Shulgin, Alexander (1991). PiHKAL: A Chemical Love Story. Berkeley, CA: Transform Press. pp. 53–56.</ref> It attained some popularity during the summer of 1967 under the name "STP" ("Serenity, Tranquility, and Peace"),<ref>"STP's faster, here's why". Berkeley Barb, June 16-22, 1967. 3-5 (Independent Voices) | 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">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref>.  
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.
Line 14: Line 14:


==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 is the amphetamine analogue of the phenethylamine [[2C-D]].<ref name=":0">http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=62</ref><ref>http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=68</ref>  
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.  
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.  
Line 21: Line 21:
==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 [[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>Sanders-Bush, Burris, KD; Knoth, K, (September 1988). "Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis" http://www.ncbi.nlm.nih.gov/pubmed/2843634</ref> However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
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.


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>Eckler JR, Chang-Fong J, Rabin RA, Smith C, Teitler M, Glennon RA, Winter JC (July 2003). "Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM". ''Pharmacology Biochemistry and Behavior''. '''75''' (4): 845–52. doi:10.1016/S0091-3057(03)00159-X. <nowiki>PMID 12957227</nowiki>. S2CID 36463979.</ref>
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" />
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" />
Line 150: Line 150:
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}


*'''[[Tramadol]]''' - Tramadol lowers the seizure threshold<ref>Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089</ref> and [[psychedelics]] may act as triggers for seizures, particularly in those who are predisposed to them.{{citation needed}}
*'''[[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>&quot;wanderlei&quot;</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>&quot;MissDja1a&quot;</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>&quot;throwaway_naut&quot;</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.{{citation needed}}
*'''[[[[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}}
*'''[https://en.wikipedia.org/wiki/Lithium_(medication) Lithium]''' - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its [[Glutamate|glutaminergic]] and [[GABA|GABAergic]] effects.{{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==
Line 162: Line 162:
*'''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>
*'''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>
*'''Belgium''': DOM is a Schedule I drug.<ref>https://www.wiv-isp.be/epidemio/epien/birn/EWS03.pdf</ref>
*'''Belgium''': DOM is a Schedule I drug.<ref>https://www.wiv-isp.be/epidemio/epien/birn/EWS03.pdf</ref>
*'''Canada''': DOM is a Schedule I drug.<ref>Controlled Drugs and Substances Act, Statutes of Canada (1996), c. C-19). Item 19.3. [https://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-13.html]</ref>
*'''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>
*'''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>
*'''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>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086</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}}
*'''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>
*'''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>https://www.legislation.gov.uk/ukpga/1971/38/schedule/2#commentary-M_F_83d9b65b-d638-43b1-ea64-c129d6f1ef0a</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}}
*'''United States''': DOM is a Schedule I drug.{{citation needed}}
*'''Czech Republic''': DOM is a Schedule I drug.<ref>https://www.zakonyprolidi.cz/cs/2013-463</ref>
*'''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==
Retrieved from "http://psy.st/wiki/DOM"