2,5-Dimethoxy-4-chloroamphetamine - Revision history

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2025-01-13T20:13:44Z

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	~~== External Links ==~~
	~~{{Commons category\|2,5-Dimethoxy-4-chloroamphetamine}}~~
	[[Category:Psychedelic phenethylamines]]		[[Category:Psychedelic phenethylamines]]
	[[Category:Substituted amphetamines]]		[[Category:Substituted amphetamines]]

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 [[File:DOC2DACS.svg|thumb|DOC2DACS.svg]] {{Short description|Chemical compound}}
 '''2,5-Dimethoxy-4-chloroamphetamine''' ('''DOC''') is a [[psychedelic]] drug and a substituted [[amphetamine]] of the [[phenethylamine]] class. It is known for its potent [[hallucinogenic]] effects and long duration of action.
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 == External Links ==
 {{Commons category|2,5-Dimethoxy-4-chloroamphetamine}}
 [[Category:Psychedelic phenethylamines]]
 [[Category:Substituted amphetamines]]
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 [[Category:Chemical compounds found in PiHKAL]]
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[[File:DOC2DACS.svg|thumb|DOC2DACS.svg]] {{Short description|Chemical compound}}
{{Infobox drug
| image = 2,5-Dimethoxy-4-chloroamphetamine_structure.png
| width = 200
| image2 =
| width2 =
| alt2 =
| caption =
| pronun =
| tradename =
| Drugs.com =
| MedlinePlus =
| licence_US =
| DailyMedID =
| pregnancy_AU =
| pregnancy_US =
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| routes_of_administration =
| ATC_prefix =
| ATC_suffix =
| legal_AU =
| legal_BR =
| legal_CA =
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| legal_NZ =
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| legal_US =
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| bioavailability =
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| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 10124-87-7
| PubChem = 5362436
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID = 4515062
| UNII =
| KEGG =
| ChEBI =
| ChEMBL =
| PDB_ligand =
| synonyms = DOC, 4-Chloro-2,5-dimethoxyamphetamine
| IUPAC_name = 1-(4-chloro-2,5-dimethoxyphenyl)propan-2-amine
| chemical_formula = C11H16ClNO2
| SMILES = CC(CC1=CC(=C(C=C1OC)Cl)OC)N
| 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 =
}}

'''2,5-Dimethoxy-4-chloroamphetamine''' ('''DOC''') is a [[psychedelic]] drug and a substituted [[amphetamine]] of the [[phenethylamine]] class. It is known for its potent [[hallucinogenic]] effects and long duration of action.

== Chemical Structure and Properties ==
DOC is chemically classified as a substituted [[amphetamine]], with the chemical formula C11H16ClNO2. It features a [[methoxy]] group at the 2 and 5 positions of the [[benzene]] ring, and a [[chloro]] group at the 4 position. The [[amphetamine]] backbone is characterized by a [[phenyl]] ring bound to an [[ethylamine]] chain.

== Pharmacology ==
DOC acts primarily as a [[serotonin receptor]] agonist, particularly at the [[5-HT2A receptor]], which is believed to be responsible for its psychedelic effects. It also has affinity for other [[serotonin receptors]], including [[5-HT2B]] and [[5-HT2C]].

== Effects ==
The effects of DOC can last from 12 to 24 hours, depending on the dose. Users report intense [[visual hallucinations]], altered perception of time, and profound changes in thought processes. Due to its potency and long duration, it is often considered a substance that should be used with caution.

== Legal Status ==
The legal status of DOC varies by country. In some jurisdictions, it is classified as a controlled substance, while in others it remains legal or unregulated. Users should be aware of the legal implications of possessing or using DOC in their respective countries.

== History ==
DOC was first synthesized by [[Alexander Shulgin]] and described in his book ''[[PiHKAL]]'' (''Phenethylamines I Have Known And Loved''). It has since gained popularity in the [[psychedelic community]] for its powerful effects and long duration.

== See Also ==
* [[2,5-Dimethoxy-4-bromoamphetamine]] (DOB)
* [[2,5-Dimethoxy-4-iodoamphetamine]] (DOI)
* [[Phenethylamine]]
* [[Psychedelic drug]]

== References ==
{{Reflist}}

== External Links ==
{{Commons category|2,5-Dimethoxy-4-chloroamphetamine}}

[[Category:Psychedelic phenethylamines]]
[[Category:Substituted amphetamines]]
[[Category:Serotonin receptor agonists]]
[[Category:Chlorobenzenes]]
[[Category:Phenethylamines]]
[[Category:Chemical compounds found in PiHKAL]]
[[Category:Medicine]]

{{medicine-stub}}