2,5-Dimethoxy-4-nitroamphetamine
Encyclopedia
2,5-Dimethoxy-4-nitroamphetamine (DON) is an analogue
of DOM
and DOB
. It is also closely related to 2C-N
, and produces hallucinogenic
, psychedelic
, and entheogen
ic effects.
s, or amphetamine
s and the full chemical name is 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine. It has an active stereocenter
and (R)-DON is the more active isomer. Concentrated solution is dark brown but transparent viscous liquid.
, Alexander Shulgin
lists a dosage of DON as being 3-4.5 mg orally. When dropped into nose, the dose is the same but onset is shorter. Dosages up to 7.5 mg reportedly produce high-intensity psychedelic effect with colorful visuals. There was a report of long-lasting psychosis in a young man after taking 12.5 mg DON hydrochloride. Unlike DOB, DON shows visible stimulation effect, including muscular activity slightly similar to amphetamine. It also has been known to be more visual than most of its psychedelic amphetamine counterparts.
receptors, primarily 5-HT2A
, 5-HT2C
and 5-HT1A
.
, however because of its close similarity in structure and effects to DOM
and DOB
, possession and sale of DON may be subject to prosecution under the Federal Analog Act
. DON is Class A in the UK after the table of contents of Pihkal and Tihkal were added to the schedules.
Analog (chemistry)
In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...
of DOM
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...
and DOB
2,5-Dimethoxy-4-bromoamphetamine
DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...
. It is also closely related to 2C-N
2C-N
2C-N, or 2,5-Dimethoxy-4-nitrophenethylamine, is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.-Chemistry:The full name of the chemical is 2-ethanamine....
, and produces hallucinogenic
Psychedelics, dissociatives and deliriants
This general group of pharmacological agents can be divided into three broad categories: psychedelics, dissociatives, and deliriants. These classes of psychoactive drugs have in common that they can cause subjective changes in perception, thought, emotion and consciousness...
, psychedelic
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
, and entheogen
Entheogen
An entheogen , in the strict sense, is a psychoactive substance used in a religious, shamanic, or spiritual context. Historically, entheogens were mostly derived from plant sources and have been used in a variety of traditional religious contexts...
ic effects.
Chemistry
DON is in a class of compounds commonly known as alpha-methyl phenethylaminePhenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
s, or amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
s and the full chemical name is 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine. It has an active stereocenter
Stereocenter
A stereocenter or stereogenic center is an atom, bearing groups such that an interchanging of any two groups leads to a stereoisomer.A chirality center is a stereocenter consisting of an atom holding a set of ligands in a spatial arrangement which is not superposable on its mirror image...
and (R)-DON is the more active isomer. Concentrated solution is dark brown but transparent viscous liquid.
Effects
DON produces psychedelic and entheogenic effects that last up to 8–30 hours. In his book PiHKAL (Phenethylamines i Have Known And Loved)PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...
, Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
lists a dosage of DON as being 3-4.5 mg orally. When dropped into nose, the dose is the same but onset is shorter. Dosages up to 7.5 mg reportedly produce high-intensity psychedelic effect with colorful visuals. There was a report of long-lasting psychosis in a young man after taking 12.5 mg DON hydrochloride. Unlike DOB, DON shows visible stimulation effect, including muscular activity slightly similar to amphetamine. It also has been known to be more visual than most of its psychedelic amphetamine counterparts.
Pharmacology
The mechanism that produces the hallucinogenic and entheogenic effects of DON is similar to that of DOB and other analogs, this being agonist activity at a number of serotoninSerotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
receptors, primarily 5-HT2A
5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
, 5-HT2C
5-HT2C receptor
The 5-HT2C receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gq/G11 and mediates excitatory neurotransmission. HTR2C denotes the human gene encoding for the receptor, that in humans is located at the...
and 5-HT1A
5-HT1A receptor
The 5-HT1A receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gi/Go and mediates inhibitory neurotransmission...
.
Legality
DON is unscheduled and unregulated in the United StatesUnited States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
, however because of its close similarity in structure and effects to DOM
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...
and DOB
2,5-Dimethoxy-4-bromoamphetamine
DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...
, possession and sale of DON may be subject to prosecution under the Federal Analog Act
Federal Analog Act
The Federal Analog Act, , is a controversial section of the United States Controlled Substances Act which allowed any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were also listed in those schedules, but only if intended for human...
. DON is Class A in the UK after the table of contents of Pihkal and Tihkal were added to the schedules.