2,5-Dimethoxy-4-bromoamphetamine
Encyclopedia
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. In his book PiHKAL (Phenethylamines i Have Known And Loved)
, Shulgin lists the dosage range as 1 to 3 mg for the racemate. The enantiopure compound dosage is at least half of that. DOB is generally taken orally. According to Shulgin, the effects of DOB typically last 18 to 30 hours. Onset of the drug is also long, sometimes taking up to three hours. The substance has been described as a more lucid, more amphetamine
-like version of LSD
, albeit far longer lasting.
and R-(–)-DOB is the eutomer
. This is an important finding as it is suggestive that it is targeting different receptors relative to most other phenethylamines (e.g. MDMA) where the R-isomer serves as the distomer
. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction
of the extremities. DOB is one of the most potent compounds in PiHKAL; while the active dose is similar to that of DOI
, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors, making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action. Omission of the amphetamine related α-methyl leads to 2C-B
, a vastly safer compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist.
(DOB racemate) DOSAGE: 1.0 - 3.0 mg. DURATION: 18 - 30 h.
There was a report of a death of a young lady following the snorting of an amount of DOB so massive, over nine milligrams of the drug was recovered from her body tissues in the postmortem examination. It was said that she and her companion had thought that the drug they were using was MDA and, taking a dosage appropriate for this, effectively overdosed themselves. He survived, following convulsions and an extended period (several weeks) of being in a comatose state. Tragic examples have been reported that involve arterial vascular spasm. But in most overdose cases ascribed to DOB, the identity of the drug has remained unestablished.
, 5-HT2B
, and 5-HT2C receptor
partial agonist
. Its psychedelic effects are mediated by its agonist
ic properties at the 5-HT2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily.
It has been suggested that DOB is a prodrug
metabolized in the lungs.
or Bromo-DragonFLY
). However, blotter paper may have a taste regardless of the chemical on it, due to ink or solvent used.
.
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...
hallucinogenic drug
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...
and a substituted amphetamine
Substituted amphetamine
Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
of the phenethylamine
Phenethylamine
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...
class of compounds, which can be used as an 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...
. DOB was first synthesized by 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...
in 1967. 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...
, Shulgin lists the dosage range as 1 to 3 mg for the racemate. The enantiopure compound dosage is at least half of that. DOB is generally taken orally. According to Shulgin, the effects of DOB typically last 18 to 30 hours. Onset of the drug is also long, sometimes taking up to three hours. The substance has been described as a more lucid, more 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,...
-like version of LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
, albeit far longer lasting.
Chemistry
The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has a stereocenterStereocenter
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-(–)-DOB is the eutomer
Eutomer
The eutomer is the molecular chiral enantiomer having the desired bioactivity, e. g. as as an active ingredient in a drug. On the other hand the enantiomer of the eutomer having the undesired bioactivity is called distomer....
. This is an important finding as it is suggestive that it is targeting different receptors relative to most other phenethylamines (e.g. MDMA) where the R-isomer serves as the distomer
Distomer
The distomer is an enantiomer in an optically active compound. It is often the case that only a single one of the enantiomers contains all of the wanted bioactivity, the distomer is often less active, has no disired activity or may even be toxic....
. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction
Vasoconstriction
Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, particularly the large arteries, small arterioles and veins. The process is the opposite of vasodilation, the widening of blood vessels. The process is particularly important in...
of the extremities. DOB is one of the most potent compounds in PiHKAL; while the active dose is similar to that of DOI
2,5-Dimethoxy-4-iodoamphetamine
2,5-dimethoxy-4-iodoamphetamine is a psychedelic drug and a substituted amphetamine of the phenethylamine family. It is also a powerful anti-inflammatory that is effective at doses on the order of 100 micrograms in humans, far below its effective dose as a psychedelic. Despite being a substituted...
, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors, making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action. Omission of the amphetamine related α-methyl leads to 2C-B
2C-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...
, a vastly safer compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist.
(DOB racemate) DOSAGE: 1.0 - 3.0 mg. DURATION: 18 - 30 h.
There was a report of a death of a young lady following the snorting of an amount of DOB so massive, over nine milligrams of the drug was recovered from her body tissues in the postmortem examination. It was said that she and her companion had thought that the drug they were using was MDA and, taking a dosage appropriate for this, effectively overdosed themselves. He survived, following convulsions and an extended period (several weeks) of being in a comatose state. Tragic examples have been reported that involve arterial vascular spasm. But in most overdose cases ascribed to DOB, the identity of the drug has remained unestablished.
Pharmacology
DOB is a 5-HT2A5-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-HT2B
5-HT2B receptor
5-hydroxytryptamine receptor 2B, also known as HTR2B, is a 5-HT2 receptor, but also denotes the human gene encoding it.-Function:...
, and 5-HT2C receptor
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...
partial agonist
Partial agonist
Partial agonists bind and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist...
. Its psychedelic effects are mediated by its agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
ic properties at the 5-HT2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily.
It has been suggested that DOB is a prodrug
Prodrug
A prodrug is a pharmacological substance administered in an inactive form. Once administered, the prodrug is metabolised in vivo into an active metabolite, a process termed bioactivation. The rationale behind the use of a prodrug is generally for absorption, distribution, metabolism, and...
metabolized in the lungs.
Misrepresentation as LSD
DOB has been sold on blotter paper (and presumably represented as LSD). Misrepresentation as LSD could be potentially dangerous, as DOB does not have the known safety profile of LSD: unlike LSD, DOB can have physically harmful (if not fatal) effects in overdose. The misrepresentation as LSD has been described by the periodical "High Times," helping some users to identify what they are actually taking. Since the mid 1980s, DOB has appeared on blotter paper and has been accidentally (or purposefully) sold as LSD. Upon tasting the chemical, if one notices a highly bitter or "chemically" taste, this should serve as a warning sign that the drug is not LSD, but likely a psychedelic amphetamine (DOB, DOC, DOIDOI
DOI or DoI may refer to:* Doi , a Japanese surname* The Bengali term for Yoghurt* Doi , or Camera no Doi, a Japanese company* Digital object identifier, a persistent identifier given to objects...
or Bromo-DragonFLY
Bromo-DragonFLY
Bromo-DragonFLY is a psychedelic hallucinogenic drug related to the phenethylamine family. Bromo-DragonFLY is considered an extremely potent hallucinogen, only slightly less potent than LSD with a normal dose in the region of 200 μg to 800 μg, and it has an extremely long duration of action up to...
). However, blotter paper may have a taste regardless of the chemical on it, due to ink or solvent used.
Legality
Internationally, DOB is a Schedule I drug under the Convention on Psychotropic SubstancesConvention on Psychotropic Substances
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, benzodiazepines, and psychedelics signed at Vienna on February 21, 1971...
.