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 amin ...
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 classificat ...
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-methylenedioxymethamph ...
, and was described in his book ''
PiHKAL'' (''Phenethylamines i Have Known And Loved'').
Chemistry
DOC is a
substituted 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 , whic ...
-
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 many ...
ated
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 amin ...
, a class of compounds commonly known as
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 ...
s. The phenethylamine equivalent (lacking the alpha-methyl group) is
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-HT2A,
5-HT2B, and
5-HT2C 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 antagonistic e ...
. 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 ...
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 of ...
" (#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 edema, liquid accumulation in the parenchyma, tissue and pulmonary alveolus, air spaces (usually alveoli) of the lungs. It leads to impaired gas exchange and may cause hypoxemia an ...
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 se ...
, 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 b ...
and in capsules was reported in late 2005 and again in late 2007. According to the
DEA
The Drug Enforcement Administration (DEA; ) is a United States federal law enforcement agency under the U.S. Department of Justice tasked with combating drug trafficking and distribution within the U.S. It is the lead agency for domestic en ...
'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 (
Ehrlich's reagent) 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 bl ...
, 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" r ...
.
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 primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territorie ...
,
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 v ...
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,
DOB, and
DOM Dom or DOM may refer to:
People and fictional characters
* Dom (given name), including fictional characters
* Dom (surname)
* Dom La Nena (born 1989), stage name of Brazilian-born cellist, singer and songwriter Dominique Pinto
* Dom people, an et ...
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 Single C ...
.
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 C ...
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 to ...
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 ...
.
See also
*
2,5-Dimethoxy-4-Substituted Amphetamines
*
DODC
*
ZDCM-04
References
External links
DOC Entry in PiHKALDOC Entry in PiHKAL infoErowid DOC Vault
{{DEFAULTSORT:Dimethoxy-4-chloroamphetamine, 2, 5-
Substituted amphetamines
Chlorobenzenes
2,5-Dimethoxyphenethylamines
Designer drugs