World Library  
Flag as Inappropriate
Email this Article


Article Id: WHEBN0003181972
Reproduction Date:

Title: 2,5-Dimethoxy-4-chloroamphetamine  
Author: World Heritage Encyclopedia
Language: English
Subject: 2C-E, 2,5-Dimethoxy-4-propylamphetamine, 2C-I, DMMDA, 2C-T-2
Collection: Amphetamines, Chloroarenes, Designer Drugs, Organochlorides, Phenol Ethers, Substituted Amphetamines
Publisher: World Heritage Encyclopedia


Ball-and-stick model of the 2,5-Dimethoxy-4-chloroamphetamine molecule
Systematic (IUPAC) name
Clinical data
Legal status
CAS Registry Number  N
PubChem CID:
ChemSpider  Y
Synonyms 2,5-Dimethoxy-4-chloroamphetamine
Chemical data
Formula C11H16ClNO2
Molecular mass 229.70 g/mol

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved).[1]


  • Chemistry 1
  • Pharmacology 2
  • Dosage 3
  • Effects 4
  • Dangers 5
  • Detection in biological specimens 6
  • Popularity 7
  • Drug prohibition laws 8
    • Canada 8.1
    • Australia 8.2
    • China 8.3
    • New Zealand 8.4
    • Denmark 8.5
    • Germany 8.6
    • Sweden 8.7
    • United Kingdom 8.8
    • USA 8.9
      • US State of Florida 8.9.1
  • See also 9
  • References 10
  • External links 11


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.


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.


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]


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.


Openly available for sale from designer drug vendors as hydrochloride 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. 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]

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.[5]


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)".[6] 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


Listed as a Schedule 1 [7] as it is an analogue of amphetamine.[8] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.[9]


Possible schedule II as an analogue of DOB .[10]


As of October 2015 DOC is a controlled substance in China.[11]

New Zealand



Denmark added DOC to the list of Schedule I controlled substances as of 8.4.2007.[10]


Scheduled in Anlage I since 22.1.2010.[10]


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.[12] 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).[13]

United Kingdom



DOC is not scheduled at the federal level in the United States,[14] but the Department of Justice considers it to be an analogue of DOB[15] and, as such, possession or sale could be prosecuted under the Federal Analogue Act.[16] In the United States, the analogues DMA, DOB, and DOM are Schedule I controlled substances.

US State of Florida

DOC is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess.[17]

See also


  1. ^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978.  
  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. ^ Baselt RC (2014). Disposition of toxic drugs and chemicals in man. Seal Beach, Ca.: Biomedical Publications. p. 2173.  
  6. ^
  7. ^ [4] (English)
  8. ^ [5] (English)
  9. ^ [6] (English)
  10. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015. 
  11. ^
  12. ^
  13. ^ §1308.11 Schedule I.
  14. ^ DEA Resources, Microgram, October 2007
  15. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

External links

  • DOC Entry in PiHKAL
  • DOC Entry in PiHKAL info
  • Erowid DOC Vault
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.