2,5-Dimethoxy-4-chloroamphetamine (DOC) is a

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace am ...

and

amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classificati ...

es. It was presumably first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymetha ...

, and was described in his book '' PiHKAL'' (''Phenethylamines i Have Known And Loved'').

Chemistry

DOC is a

substituted A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions ar ...

alpha Alpha (uppercase , lowercase ; grc, ἄλφα, ''álpha'', or ell, άλφα, álfa) is the first letter of the Greek alphabet. In the system of Greek numerals, it has a value of one. Alpha is derived from the Phoenician letter aleph , whi ...

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ...

ated

, a class of compounds commonly known as

s. The phenethylamine equivalent (lacking the alpha-methyl group) is

2C-C 2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', Shulgin lists the dosage range as 20–40 mg. 2C-C ...

. DOC has a

stereocenter In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups c ...

and (''R'')-(−)-DOC is the more active

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

Pharmacology

DOC acts as a selective 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonis ...

. Its psychedelic effects are mediated via its actions on the 5-HT_2A receptor.

Dosage

A normal average dose of DOC ranges from 0.5–7.0 mg 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.

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 closed eye visuals, increased awareness of sound and movement, and euphoria. In the autobiography PiHKAL, Alexander Shulgin included a description of DOC as "an

archetypal The concept of an archetype (; ) appears in areas relating to behavior, historical psychology, and literary analysis. An archetype can be any of the following: # a statement, pattern of behavior, prototype, "first" form, or a main model that o ...

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...

" (#64); its presumed full-range visual, audio, physical, and mental effects show exhilarating clarity, and some overwhelming, humbling, and "composting"/interweaving effects.

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. 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

pulmonary edema Pulmonary edema, also known as pulmonary congestion, is excessive liquid accumulation in the tissue and air spaces (usually alveoli) of the lungs. It leads to impaired gas exchange and may cause hypoxemia and respiratory failure. It is due ...

and a

subgaleal hemorrhage Subgaleal hemorrhage, also known as subgaleal hematoma, is bleeding in the potential space between the skull periosteum and the scalp galea aponeurosis. Symptoms The diagnosis is generally clinical, with a fluctuant boggy mass developing over the ...

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.

Popularity

Although rare on the

black market A black market, underground economy, or shadow economy is a clandestine market or series of transactions that has some aspect of illegality or is characterized by noncompliance with an institutional set of rules. If the rule defines 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

blotting paper Blotting paper, called bibulous paper, is a highly absorbent type of paper or other material. It is used to absorb an excess of liquid substances (such as ink or oil) from the surface of writing paper or objects. Blotting paper referred to as ...

and in capsules was reported in late 2005 and again in late 2007. According to the DEA'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

LSD Lysergic acid diethylamide (LSD), also known colloquially as acid, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, vi ...

'blotter acid'". They added "Unusually, the paper appeared to be hand-lined using two pens, in squares measuring approximately 6 x 6

millimeters 330px, Different lengths as in respect to the electromagnetic spectrum, measured by the metre and its derived scales. The microwave is between 1 meter to 1 millimeter. The millimetre (American and British English spelling differences#-re, -er, ...

. The paper displayed fluorescence when irradiated at 365

nanometers 330px, Different lengths as in respect to the molecular scale. The nanometre (international spelling as used by the International Bureau of Weights and Measures; SI symbol: nm) or nanometer (American and British English spelling differences#-re ...

; however, color testing for LSD with

para-dimethylaminobenzaldehyde ''para''-Dimethylaminobenzaldehyde is an organic compound containing amine and aldehyde moieties which is used in Ehrlich's reagent and Kovac's reagent to test for indoles. The carbonyl group typically reacts with the electron rich 2-position ...

(

Ehrlich's reagent Ehrlich's reagent or Ehrlich reagent is a reagent containing ''p''-dimethylaminobenzaldehyde (DMAB) and thus can act as an indicator to presumptively identify indoles and urobilinogen. Several Ehrlich tests use the reagent in a medical test; so ...

) 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)". 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 Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high b ...

, as amphetamine compounds are known to cause sharp increases in systolic

blood pressure Blood pressure (BP) is the pressure of circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term "blood pressure ...

Drug prohibition laws

Canada

Listed as a

Schedule 1 Schedule 1 may refer to: * Schedule I Controlled Substances within the US Controlled Substances Act * Schedule I Controlled Drugs and Substances within the Canadian Controlled Drugs and Substances Act * Schedule I Psychotropic Substances within t ...

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

Australia

Unscheduled but can be controlled as schedule II as an analogue of DOB.

China

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

New Zealand

Scheduled.

Denmark

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

Germany

Scheduled in Anlage I since 22.1.2010.

Sweden

''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. 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).

United Kingdom

Class A.

United States

DOC is not scheduled or controlled at the federal level in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...

, but the

Department of Justice A justice ministry, ministry of justice, or department of justice is a ministry or other government agency in charge of the administration of justice. The ministry or department is often headed by a minister of justice (minister for justice in a ...

considers it to be an analogue of DOB and, as such, possession or sale could be prosecuted under the

Federal Analogue Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ...

. In the United States, the analogues

DMA DMA may refer to: Arts * DMA (magazine), ''DMA'' (magazine), a defunct dance music magazine * Dallas Museum of Art, an art museum in Texas, US * Danish Music Awards, an award show held in Denmark * BT Digital Music Awards, an annual event in the U ...

, DOB, and DOM are Schedule I

controlled substances A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Si ...

US State of Florida

DOC is a Schedule I

controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Single ...

in the state of

Florida Florida is a state located in the Southeastern region of the United States. Florida is bordered to the west by the Gulf of Mexico, to the northwest by Alabama, to the north by Georgia, to the east by the Bahamas and Atlantic Ocean, and ...

making it illegal to buy, sell, or possess.

United Nations

In December 2019, the

UNODC The United Nations Office on Drugs and Crime (UNODC; French: ''Office des Nations unies contre la drogue et le crime'') is a United Nations office that was established in 1997 as the Office for Drug Control and Crime Prevention by combining the ...

announced scheduling recommendations placing DOC into Schedule I alongside another several

research chemicals Research chemicals are chemical substances used by scientists for medical and scientific research purposes. One characteristic of a research chemical is that it is for laboratory research use only; a research chemical is not intended for human o ...

References

External links

DOC Entry in PiHKAL

DOC Entry in PiHKAL info

Erowid DOC Vault
{{DEFAULTSORT:Dimethoxy-4-chloroamphetamine, 2, 5- Substituted amphetamines Chlorobenzenes 2,5-Dimethoxyphenethylamines Designer drugs