View source for 4-Chloro-2,5-dimethoxyamphetamine

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{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em"
|-----
! colspan="2" bgcolor="#cccccc" | DOC
|-----
| [[IUPAC nomenclature|Chemical name]]
| 4-chloro-2,5-Dimethoxy-amphetamine or<br>1-(4-chloro-2,5-dimethoxyphenyl)-2-aminopropane
|-----
| [[Chemical formula]]
| C<sub>11</sub>H<sub>16</sub>NO<sub>2</sub>
|-----
| [[Molar mass]]
| 229.70628 <math>\begin{matrix} \frac{g}{mol} \end{matrix}</math><br>266.16692 <math>\begin{matrix} \frac{g}{mol} \end{matrix}</math> (hydrochloride salt)
|-----
| [[Melting point]]
| 187-188 °C and 193-194.5 ([[hydrochloride]])
|-----
| [[CAS registry number|CAS numbers]] ||         ?        
|-----
| [[Simplified molecular input line entry specification|SMILES]]
| COc1cc(C[C@@H](C)N)c(cc1Cl)OC
|}
{{SI}}

==Overview==
'''4-Chloro-2,5-dimethoxyamphetamine''' or '''2,5-dimethoxy-4-chloroamphetamine'''  or '''4-Chloro-2,5-DMA''' or '''DOC''' is a [[psychedelic]] [[hallucinogenic drug]] of the phenethylamine family.  Used by some as an [[entheogen]], DOC was presumably first synthesized by [[Alexander Shulgin]].  The drug is generally taken orally, but some users have been known to [[insufflate]] or [[smoke]] the pure powder.

==Chemistry==

DOC is a substituted alpha-[[methyl]]ated [[phenethylamine]], a class of compounds commonly known as [[amphetamine]]s.  The full name of the chemical is 2,5-di[[methoxy]]-4-[[chloro]]-amphetamine. DOC has a [[stereocenter]] and ''R''-(-)-DOC is the more active [[stereoisomer]].  DOC is the 3-[[carbon]] chain [[homologous series|homologue]] of the psychedelic [[2C-C]].

==Dosage==

A normal average dose of DOC ranges from .5-8.0 mg; the former producing threshold effects, and the latter producing extremely strong effects. Doses up to 10mg have been known to send the user into a restless stupor. Onset of the drug is 1-3 hours, peak and plateau at 4-8 hours, and a gradual come down. After effects can last well into the next day.

==Effects==

Unlike simple amphetamines, DOC is a psychedelic that resembles [[LSD]], [[2,5-Dimethoxy-4-bromoamphetamine|DOB]], and [[mescaline]].  These effects include open and closed eye visuals, increased awareness of sound and movement and euphoria.

==Pharmacology==

The mechanism of DOC’s hallucinogenic effects is unknown, but like DOB and DOI, it may be mediated by partial [[agonist]]ic activity at the 5-HT<sub>2A</sub> [[5-HT receptor|serotonin receptor]], and [[binding]] [[affinity]] for the 5-HT<sub>2B</sub> and the 5-HT<sub>2C</sub> [[serotonin]] [[receptor (biochemistry)|receptor]].

==Dangers==

The toxicity of DOC is not known, but nausea, [[chest]] [[Pain and nociception|pains]], and [[vasoconstriction]] have been reported by some users.  In June 2006 four teenagers were admitted to a hospital in Metropolitan Detroit, Michigan after accidentally overdosing DOC.[http://www.detnews.com/apps/pbcs.dll/article?AID=/20060603/METRO/606030332&SearchID=73247070138485]  To date, there have been no deaths attributed to DOC.  However, DOC is an extremely potent [[psychoactive]], and the risk of overdose is great if unknown or extreme dosages are taken.

==Popularity==

Although rare on the black market, sales of DOC on [[blotting paper]] and in capsules was reported in late 2005.  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.

==Legality==

4-chloro-2,5-dimethoxyamphetamine is unscheduled in the United States. It is likely that it would be considered an analogue (of DOB or DOM), in which case, sales for human consumption or possession with the intent to ingest could be prosecuted under the Federal Analogue Act. In the United States, the analogues 2,5-dimethoxyamphetamine, 4-bromo-2,5-dimethoxyamphetamine, and 4-methyl-2,5-dimethoxyamphetamine are Schedule I controlled substances.  DOC is scheduled in many other countries including Canada, Germany, New Zealand, Sweden and the UK.

==See also==

*[[2,5-Dimethoxy-4-iodoamphetamine|DOI]]
*[[2,5-Dimethoxy-4-bromoamphetamine|DOB]]
*[[PiHKAL]]

==External links==
*[http://www.erowid.org/library/books_online/pihkal/pihkal064.shtml DOC Entry in PIHKAL]
*[http://www.erowid.org/chemicals/doc/doc.shtml Erowid DOC Vault]

==Categorization==
{{Hallucinogenic phenethylamines}}
{{PiHKAL}}

[[Category:Amphetamines|Chloro-2,5-dimethoxyamphetamine, 4-]]
[[Category:Psychedelic phenethylamines|Chloro-2,5-dimethoxyamphetamine, 4-]]
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