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Revision as of 17:06, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 470106376 of page 2,5-Dimethoxy-4-chloroamphetamine for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 11:29, 28 April 2024 edit 2600:1702:2610:1ca0:a825:391c:cd55:859f (talk) →Dosage: I'm a normal user and that's how you should start off giving people 0.5 can be to much for beginnersTags: Mobile edit Mobile web edit 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 407451900
| Watchedfields = changed
| IUPAC_name = 1-(4-chloro-2,5-dimethoxy-phenyl)propan-2-amine
| verifiedrevid = 477211612
| image = 4-chloro-2,5-dimethoxyamphetamine.svg
| IUPAC_name = 1-(4-Chloro-2,5-dimethoxyphenyl)propan-2-amine
| width = 230px
| image = DOC2DACS.svg

| width = 150px
| image2 = 2,5-Dimethoxy-4-chloroamphetamine molecule ball.png
| width2 = 150px
| alt2 = Ball-and-stick model of the 2,5-Dimethoxy-4-chloroamphetamine molecule
<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| legal_AU = Unscheduled | legal_AU = Unscheduled
| legal_BR = F2
| legal_CA = Schedule III
| 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=] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_CA = Schedule I
| legal_DE = Anlage I
| legal_UK = Class A | legal_UK = Class A
| legal_US = Unscheduled | legal_US = Unscheduled
| legal_UN = P I


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 123431-31-2 --> | CAS_number = 123431-31-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8Y1C6K0PCA
| PubChem = 542036 | PubChem = 542036
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22719
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 472008 | ChemSpiderID = 472008
Line 24: Line 36:
<!--Chemical data--> <!--Chemical data-->
| C=11 | H=16 | Cl=1 | N=1 | O=2 | C=11 | H=16 | Cl=1 | N=1 | O=2
| smiles = ClC1=C(OC)C=C(CC(C)N)C(OC)=C1
| molecular_weight = 229.70 g/mol
| smiles = Clc1cc(OC)c(cc1OC)CC(N)C
| InChI = 1/C11H16ClNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
| InChIKey = ACRITBNCBMTINK-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H16ClNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 | StdInChI = 1S/C11H16ClNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ACRITBNCBMTINK-UHFFFAOYSA-N | StdInChIKey = ACRITBNCBMTINK-UHFFFAOYSA-N
| synonyms = 2,5-dimethoxy-4-chloroamphetamine | synonyms = 2,5-Dimethoxy-4-chloroamphetamine
}} }}
{{commonscat}}

'''2,5-Dimethoxy-4-chloroamphetamine''' ('''DOC''') is a ] of the ] and ] ]es. It was presumably first ] by ], and was described in his book '']'' (''Phenethylamines i Have Known And Loved'').<ref name="PiHKAL">{{cite book | title = PiHKAL: A Chemical Love Story | vauthors = Shulgin A, Shulgin A | publisher = Transform Press | location = United States | isbn = 0-9630096-0-5 | page = 978 | url = http://www.erowid.org/library/books_online/pihkal/pihkal.shtml| access-date= 30 November 2009 | archive-url= https://web.archive.org/web/20100103030739/http://www.erowid.org/library/books_online/pihkal/pihkal.shtml| archive-date= 3 January 2010| url-status= live |date= September 1991}}</ref>

== Chemistry ==

DOC is a ] ]-]ated ], a class of compounds commonly known as ]s. The phenethylamine equivalent (lacking the alpha-methyl group) is ]. DOC has a ] and (''R'')-(−)-DOC is the more active ].

== Pharmacology ==

DOC acts as a selective ], and ] ]. Its psychedelic effects are mediated via its actions on the 5-HT<sub>2A</sub> receptor.{{Citation needed|date=June 2023}}

== Dosage ==

A normal average dose of DOC ranges from 0.2–7.0 ]<ref name="Erowid DOC Vault: Dosage">{{cite web|url=http://www.erowid.org/chemicals/doc/doc_dose.shtml |title=Erowid DOC Vault: Dosage |access-date=22 April 2008 |archive-url=https://web.archive.org/web/20080502003536/http://www.erowid.org/chemicals/doc/doc_dose.shtml |archive-date=2 May 2008 |url-status=live }}</ref> the former producing threshold effects, and the latter producing extremely strong effects. Onset of the drug is 1–3 hours, peak and plateau at 4–8 hours, and a gradual come down with residual stimulation at 9-20h. After effects can last well into the next day.<ref name="Erowid DOC Vault: Dosage"/><ref name="urlErowid Online Books: PiHKAL - #64 DOC">{{cite web |url=https://www.erowid.org/library/books_online/pihkal/pihkal064.shtml |title=Erowid Online Books: "PiHKAL" - #64 DOC |url-status=live |archive-url=https://archive.today/20180803005530/https://www.erowid.org/library/books_online/pihkal/pihkal064.shtml |archive-date=3 August 2018 |access-date=17 November 2005 <!--DASHBot--> }}</ref>

== Effects ==
Unlike simple amphetamines, DOC is considered a chemical that influences cognitive and perception processes of the brain. The strongest supposed effects include open and ], increased awareness of sound and movement, and euphoria. In the autobiography PiHKAL, Alexander Shulgin included a description of DOC as "an ] ]" (#64); its presumed full-range visual, audio, physical, and mental effects show exhilarating clarity, and some overwhelming, humbling, and "composting"/interweaving effects.<ref name="urlErowid Online Books: PiHKAL - #64 DOC"/>

== Dangers ==

Very little data exists about the toxicity of DOC. In April 2013, a case of death due to DOC was reported. The source does not specify whether the drug alone caused the death.<ref>{{cite news | vauthors = Bucks J |date=2013-04-25 |title="Moment of madness": rare drug implicated in student death |newspaper=The Saint |url=http://www.thesaint-online.com/2013/04/moment-of-madness-rare-drug-implicated-in-student-death/ |url-status=dead |access-date=2013-04-25 |archive-url=https://web.archive.org/web/20130428055435/http://www.thesaint-online.com/2013/04/moment-of-madness-rare-drug-implicated-in-student-death/ |archive-date=2013-04-28 |df=dmy-all}}</ref> In 2014, a death was reported in which DOC was directly implicated as the sole causative agent in the death of a user. The autopsy indicated ] and a ].<ref>{{cite journal | vauthors = Barnett RY, Baker DD, Kelly NE, McGuire CE, Fassette TC, Gorniak JM | title = A fatal intoxication of 2,5-dimethoxy-4-chloroamphetamine: a case report | journal = Journal of Analytical Toxicology | volume = 38 | issue = 8 | pages = 589–91 | date = October 2014 | pmid = 25217551 | doi = 10.1093/jat/bku087 | doi-access = free }}</ref>

== Detection in biological specimens ==
DOC may be quantitated in blood, plasma or urine by gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry to confirm a diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Blood or plasma DOC concentrations are expected to be in a range of 1–10 μg/L in persons using the drug recreationally, >20 μg/L in intoxicated patients and >100 μg/L in victims of acute overdosage.<ref>{{cite book |title=Disposition of toxic drugs and chemicals in man |vauthors=Baselt RC |publisher=Biomedical Publications |year=2014 |isbn=978-0-9626523-9-4 |location=Seal Beach, California |page=2173 |language=en}}</ref>

== Popularity ==

Although rare on the ], it has been available in bulk and shipped worldwide by select elite "Grey Market" Research Chemical suppliers for several years. Sales of DOC on ] and in capsules was reported in late 2005 and again in late 2007. According to the ]'s Microgram from December 2007, the Concord Police Department in Contra Costa County, California, in the US, seized "a small piece of crudely lined white blotter paper without any design, suspected ] 'blotter acid'". They added "Unusually, the paper appeared to be hand-lined using two pens, in squares measuring approximately 6 x 6 ]. The paper displayed fluorescence when irradiated at 365 ]; however, color testing for LSD with ] (]) was negative. Analysis of a methanol extract by GC/MS indicated not LSD but rather DOC (not quantitated but a high loading based on the TIC)".<ref>{{cite web |url=https://www.justice.gov/dea/pr/micrograms/2007/mg1207.pdf |title=mg1207 |access-date=2013-08-13 |archive-url=https://web.archive.org/web/20121017234332/http://www.justice.gov/dea/pr/micrograms/2007/mg1207.pdf |archive-date=2012-10-17 |url-status=dead }}</ref> DOC is sometimes misrepresented as LSD by unscrupulous dealers. This is particularly dangerous, as DOC is not known to have the safety profile of LSD. It can be particularly unsafe, in comparison to LSD, for those suffering from ], as amphetamine compounds are known to cause sharp increases in systolic ].

== Drug prohibition laws ==

===Canada===
Listed as a ]<ref name="CDSA Schedule I: Amphetamines">{{cite web |date=2022-03-31 |title=Schedule I |url=http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C |url-status=live |archive-url=https://archive.today/20220331223632/http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C |archive-date=2022-03-31 |access-date=2022-03-31 |work=Controlled Drugs and Substances Act |publisher=Canadian Legal Information Institute }}</ref> as it is an analogue of amphetamine.<ref name="Definitions and Interpretations">{{cite web |title=Controlled Drugs and Substances Act |url=http://isomerdesign.com/Cdsa/definitions.php?structure=C |work=Definitions and interpretations |publisher=Canadian Legal Information Institute |access-date=2022-03-31 |archive-date=2013-11-10 |archive-url=https://web.archive.org/web/20131110213450/http://isomerdesign.com/Cdsa/definitions.php?structure=C |url-status=dead }}</ref> The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.<ref name="Safe Streets Act">{{cite web | title = Backgrounder: The Safe Streets and Communities Act Four Components Coming Into Force | work = Canadian Department of Justice | url = http://www.justice.gc.ca/eng/news-nouv/nr-cp/2012/doc_32759.html | archive-url = https://web.archive.org/web/20121018122345/http://www.justice.gc.ca/eng/news-nouv/nr-cp/2012/doc_32759.html | archive-date = 2012-10-18 }}</ref>

===Australia===
Unscheduled but can be controlled as schedule II as an analogue of DOB.<ref name="Erowid DOC Vault: Legal Status">{{cite web|url=http://www.erowid.org/chemicals/doc/doc_law.shtml |title=Erowid DOC Vault: Legal Status |access-date=22 April 2008 |archive-url=https://web.archive.org/web/20080501231821/http://www.erowid.org/chemicals/doc/doc_law.shtml |archive-date=1 May 2008 |url-status=live }}</ref>

===China===
As of October 2015 DOC is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

===New Zealand===
Scheduled.<ref name="Erowid DOC Vault: Legal Status"/>

===Denmark===
Denmark added DOC to the list of Schedule I controlled substances as of 8.4.2007.<ref name="Erowid DOC Vault: Legal Status"/>

===Germany===
Scheduled in Anlage I since 22.1.2010.<ref name="Erowid DOC Vault: Legal Status"/>

===Sweden===
] added DOC to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as narcotics in Sweden as of Aug 30, 2007, published by ] in their regulation '''LVFS 2007:10''' listed as '''DOC, 4-klor-2,5-dimetoxi-amfetamin'''.<ref>{{Cite web|url=http://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf|title = Läkemedelsverkets föreskrifter - LVFS och HSLF-FS &#124; Läkemedelsverket}}</ref>
DOC was first classified by ] health ministry ] as "health hazard" under the act ] (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') as of Jul 1, 2004, in their regulation '''SFS 2004:486''' listed as '''4-klor-2,5-dimetoxiamfetamin (DOC)'''.<ref>{{cite web |title=Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor |url=http://www.notisum.se/rnp/sls/sfs/20040486.pdf |archive-url=https://web.archive.org/web/20180915141627/http://www.notisum.se/rnp/sls/sfs/20040486.pdf |archive-date=15 September 2018 |language=Swedish |date=27 May 2004}}</ref>
===United Kingdom===
Class A.<ref name="Erowid DOC Vault: Legal Status"/>

===United States===
DOC is not scheduled or controlled at the federal level in the ],<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{cite web|url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm|title=PART 1308 - Section 1308.11 Schedule I|website=www.deadiversion.usdoj.gov|access-date=31 March 2018|archive-date=27 August 2009|archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm|url-status=dead}}</ref> but the ] considers it to be an analogue of ]<ref>{{cite web |url=https://www.justice.gov/dea/pr/micrograms/2007/mg1007.pdf |title=DEA Resources, Microgram, October 2007 |access-date=2012-10-03 |archive-url=https://web.archive.org/web/20121017234351/http://www.justice.gov/dea/pr/micrograms/2007/mg1007.pdf |archive-date=2012-10-17 |url-status=dead }}</ref> and, as such, possession or sale could be prosecuted under the ].<ref name="Erowid DOC Vault: Legal Status"/> In December 2023, the US ] issued a ] that would classify both 2,5-dimethoxy-4-chloroamphetamine and ] as schedule I controlled substances.<ref name="Federal Register 2023">{{cite web |url=https://www.regulations.gov/document/DEA-2022-0026-0001/comment |title=Schedules of Controlled Substances: Placement of 2,5-dimethoxy-4-iodoamphetamine (DOI) and 2,5-dimethoxy-4-chloroamphetamine (DOC) in Schedule I |website=www.regulations.gov}}</ref>

In the United States, the analogues ], ], and ] are Schedule I ].

====US State of Florida====
DOC is a Schedule I ] in the state of ] making it illegal to buy, sell, or possess.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL">{{cite web|url=http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html|title=The 2017 Florida Statutes - Title XLVI - CRIMES - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL|website=leg.state.fl.us|access-date=31 March 2018}}</ref>

===United Nations===
In December 2019, the ] announced scheduling recommendations placing DOC into Schedule I alongside another several ].<ref>{{cite web|url=https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3|title=December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling}}</ref>

== See also ==
* ]s
* ]
* ]

== References ==
{{Reflist|2}}

== External links ==
*
*
*

{{Hallucinogens}}
{{Serotonergics}}
{{Phenethylamines}}

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