2,5-Dimethoxy-4-chloroamphetamine

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2,5-Dimethoxy-4-chloroamphetamine
DOC2DACS.svg
Systematic (IUPAC) name
1-(4-chloro-2,5-dimethoxy-phenyl)propan-2-amine
Clinical data
Legal status Unscheduled (AU) Schedule III (CA) Class A (UK) Unscheduled (US)
Identifiers
CAS number 123431-31-2 N
ATC code ?
PubChem CID 542036
ChemSpider 472008 YesY
ChEMBL CHEMBL8100 YesY
Synonyms 2,5-dimethoxy-4-chloroamphetamine
Chemical data
Formula C11H16ClNO2 
Mol. mass 229.70 g/mol
 N (what is this?)  (verify)

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was presumably first synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved).[1]

Chemistry[edit]

DOC is a substituted alpha-methylated phenethylamine, a class of compounds commonly known as amphetamines. The phenethylamine equivalent (lacking the alpha-methyl group) is 2C-C. DOC has a stereocenter and R-(-)-DOC is the more active stereoisomer.

Pharmacology[edit]

DOC acts as a selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist. Its psychedelic effects are mediated via its actions on the 5-HT2A receptor.[citation needed]

Dosage[edit]

A normal average dose of DOC ranges from 0.5–7.0 mg[2] 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[2][3]

Effects[edit]

Unlike simple amphetamines, DOC is considered a chemical that influences cognitive and perception processes of the brain. The strongest supposed effects include open and closed eye visuals, increased awareness of sound and movement, and euphoria. In the autobiography PiHKAL, Alexander Shulgin refers to DOC as an "archetypal psychedelic" (#64); its presumed full-range visual, audio, physical, and mental effects show exhilarating clarity, and some overwhelming, humbling, and "composting"/interweaving effects.

Dangers[edit]

Openly available for sale and shipment worldwide from Research Chemical vendors for several years as high purity hcl salt, not only does the dosage require precision to the milligram, it is easily laid onto blotter paper and misrepresented as LSD, which creates significant additional danger in the chance of poly-substance use. The toxicity of DOC is not known, but nausea, chest pains, and vasoconstriction have been reported by some users. There has been at least one case of anion gap metabolic acidosis with respiratory failure requiring care in an intensive care unit following ingestion of the drug, as well as a fatality via respiratory depression currently awaiting autopsy to check for a possible drug combination interaction.[citation needed] In April 2013, a case of death due to DOC was reported. The source does not specify whether the drug alone caused the death.[4]

Popularity[edit]

Although rare on the black market, it has been available in bulk and shipped worldwide by select elite "Grey Market" Research Chemical suppliers for several years. Sales of DOC on blotting paper and in capsules was reported in late 2005 and again in late 2007. According to the DEA [ December Microgram], 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 LSD 'blotter acid'". They added "Unusually, the paper appeared to be hand-lined using two pens, in squares measuring approximately 6 x 6 millimeters. The paper displayed fluorescence when irradiated at 365 nanometers; however, color testing for LSD with para-dimethylaminobenzaldehyde (PDMAB) 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)".[5] 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 hypertension, as amphetamine compounds are known to cause sharp increases in systolic blood pressure.

Drug prohibition laws[edit]

Canada[edit]

Listed as a Schedule 1 [6] as it is an analogue of amphetamine.[7] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.[8]

Australia[edit]

Scheduled.[9]

New Zealand[edit]

Scheduled.[9]

Denmark[edit]

Denmark added DOC to the list of Schedule I controlled substances as of 8.4.2007.[9]

Germany[edit]

Scheduled in Anlage I since 22.1.2010.[9]

Sweden[edit]

Sveriges riksdag 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 Medical Products Agency in their regulation LVFS 2007:10 listed as DOC, 4-klor-2,5-dimetoxi-amfetamin.[10] DOC was first classified by Sveriges riksdags health ministry Statens folkhälsoinstitut as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (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).[11]

United Kingdom[edit]

Scheduled.[9]

USA[edit]

DOC is unscheduled in the United States. The Department of Justice considers it to be an analogue of DOB[12] and, as such, sales for human consumption or possession with the intent to ingest could be prosecuted under the Federal Analogue Act.[9] In the United States, the analogues DMA, DOB, and DOM are Schedule I controlled substances.

See also[edit]

References[edit]

  1. ^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5. Archived from the original on 3 January 2010. Retrieved 30 November 2009. 
  2. ^ a b "Erowid DOC Vault : Dosage". Archived from the original on 2 May 2008. Retrieved 22 April 2008. 
  3. ^ "Erowid Online Books : "PiHKAL" - #64 DOC". Retrieved 17 November 2005. 
  4. ^ Bucks, Jonathan (25 April 2013). ""Moment of madness": rare drug implicated in student death". The Saint. Retrieved 25 April 2013. 
  5. ^ http://www.justice.gov/dea/pr/micrograms/2007/mg1207.pdf
  6. ^ [1] (English)
  7. ^ [2] (English)
  8. ^ [3] (English)
  9. ^ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf
  10. ^ http://www.notisum.se/rnp/sls/sfs/20040486.pdf
  11. ^ DEA Resources, Microgram, October 2007

External links[edit]