DOB
DOB is a psychedelic amphetamine of the DOx family, first synthesized by Alexander Shulgin in 1967 and later documented in depth in his 1991 book PiHKAL. It was for many years considered the most potent known phenethylamine psychedelic.1 DOB is characterized by its unusually long duration of action and notably slow onset, which can take up to three hours — a property that increases the risk of accidental redosing.
Contents
Dosage & Duration
Dosage
The onset of DOB is characteristically slow, with full effects often not manifesting until one to two hours after ingestion. Attempting to redose before this onset period has concluded substantially elevates the risk of overdose. Physical stimulation and difficulty sleeping frequently outlast the main psychedelic effects and can continue for an extended period, sometimes reaching 36 hours following larger doses.
Duration
Subjective Effects
Effects vary widely by individual, dose, and context.
Physical
The physical effects of DOB can be broken down into five components all of which progressively intensify proportional to dosage.
Cognitive
The head space of DOB is described by many as one of mental stimulation and a powerful enhancement of a person's current mental state. Many users report that it may not be as deep as other traditional psychedelics such as LSD or Psilocin and that it is comparatively empty in terms of its insightfulness.
Visual
Distortions
DOB presents a full and complete array of possible visual distortions.
Enhancements
DOB presents a full and complete array of possible visual enhancements.
Geometry
The visual geometry that is present throughout this trip can be described as more similar in appearance to that of LSD, 25I-NBOMe or 2C-B than that of Ayahuasca, Psilocin or 2C-E. They can be comprehensively described as unstructured in their organization, algorithmic in geometric style, intricate in complexity, small in size, fast and smooth in motion, colourful in scheme, glossy in colour, sharp in their edges and equally rounded and angular in their corners. They give off a synthetic feel to them that at higher dosages are significantly more likely to result in states of Level 7A visual geometry over Level 7B.
Hallucinatory States
DOB is capable of producing a full range of low and high level hallucinatory states in a fashion that is significantly less consistent and reproducible than that of many other commonly used psychedelics.
Auditory
The auditory effects of DOB are common in their occurrence and exhibit a full range of effects.
Reagent Testing
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Pharmacology
Pharmacodynamics
DOB acts as a partial agonist at the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, with its psychedelic effects primarily mediated through 5-HT2A activation.2 It displays notable selectivity for the 5-HT2 receptor subfamily and demonstrates high efficacy in triggering downstream 5-HT2 receptor-mediated signaling.2 DOB is also a very weak agonist at the human trace amine-associated receptor 1 (TAAR1). The compound is typically encountered as a racemate, with R-(−)-DOB serving as the more pharmacologically active enantiomer.2
Pharmacokinetics
DOB is extensively metabolized, with only a small amount of unchanged drug excreted. Metabolism proceeds through O-demethylation (at least partly catalyzed by CYP2D6),34 oxidative deamination, and reduction to corresponding alcohols.4 DOB has been reported to weakly inhibit CYP2D6, though likely not to a degree sufficient to cause significant drug interactions.3 Following intravenous administration, the drug initially accumulates in the lungs before distributing to the liver and brain;5 after oral administration, a similar distribution pattern is observed without the initial pulmonary concentration. It has been suggested that DOB may function as a prodrug that undergoes metabolism in the lungs.6
Dangerous
Highest riskThese combinations are considered extremely harmful and should always be avoided. Reactions to these drugs taken in combination are highly unpredictable and have a potential to cause death.
Unsafe
AvoidThere is considerable risk of physical harm when taking these combinations, they should be avoided where possible.
Caution
Use cautionThese combinations are not usually physically harmful, but may produce undesirable effects, such as physical discomfort or overstimulation. Extreme use may cause physical health issues. Synergistic effects may be unpredictable. Care should be taken when choosing to use this combination.
Tolerance
Serotonergic psychedelics, 5-HT2A agonists
Harm Potential
Addiction & Dependence
Psychological
Extremely LowDOB is not habit-forming and the desire to use it typically decreases with use. It is most often self-regulating, with many users experiencing a naturally limiting quality to the substance.
Physical
Extremely LowDOB is not physically addictive and does not produce physical dependence or withdrawal symptoms.
Toxicity
Severe vasoconstriction is the primary toxicity concern, developing progressively and peaking several hours into intoxication; at overdose levels this has resulted in diffuse arterial spasm, peripheral vasospasm, and in extreme cases gangrene requiring amputation of extremities.7
Overdose can produce convulsions and seizure activity, typically occurring alongside other severe symptoms such as coma, metabolic acidosis, and cerebral edema; at typical recreational doses, the primary concerns are confusion, attention lapses, and sleep disturbances.8
Psychosis Risk
The long duration and stimulating nature of DOB increase the risk of psychological disturbance. Use can trigger latent psychoses, and frequent use carries risk of loss of reality that may manifest as anxiety states or schizophrenic traits. As sleep deprivation accumulates during extended experiences, stimulant psychosis may emerge with external hallucinations blending into psychedelic visuals around the 16-24 hour mark. Overdose can produce bizarre, delusional, and sometimes violent behavior.
Seizure Risk
Seizures are primarily a concern at overdose levels rather than at typical recreational doses. Convulsive activity has been documented in multiple overdose case reports, sometimes contributing to fatal outcomes.8 The seizure threshold may be lowered when combined with other substances such as tramadol.
History & Culture
Discovery and Early Research
DOB was first synthesized by Alexander Shulgin in 1967 as part of research examining how 4-position substitutions affect metabolic stability in phenethylamine compounds. The first published scientific report appeared in 1971, documenting toxicology findings and initial pharmacological…
Trip Reports
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Legality
International
1961 Single Convention: DOB is not individually scheduled.
1971 Convention on Psychotropic Substances: DOB is scheduled in Schedule I.
1988 Convention: DOB is not listed in precursor Tables I or II.
By Country
References
Source Pages
Citations
- Shulgin, A., & Shulgin, A.. (1991). PiHKAL: #62 DOB. PiHKAL: A Chemical Love Story. https://erowid.org/library/books_online/pihkal/pihkal062.shtml1
- (2005). Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. https://doi.org/10.1111/j.1471-4159.2005.03477.x123
- Dinger, J., Meyer, M. R., & Maurer, H. H.. (2008). 2,5-Dimethoxyamphetamine-derived designer drugs: studies on the identification of cytochrome P450 (CYP) isoenzymes involved in formation of their main metabolites and on their capability to inhibit CYP2D6. Toxicology Letters, 183(1-3), 52-57. https://doi.org/10.1016/j.toxlet.2008.09.01412
- Ewald, A. H., Fritschi, G., Bork, W. R., & Maurer, H. H.. (2006). Designer drugs 2,5-dimethoxy-4-bromo-amphetamine (DOB) and 2,5-dimethoxy-4-bromo-methamphetamine (MDOB): studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. Journal of Mass Spectrometry, 41(4), 487-498. https://doi.org/10.1002/jms.100712
- Nakagawa, T., & et al.. (2007). Distribution profile of 2,5-dimethoxy-4-bromoamphetamine (DOB) in rats after oral and subcutaneous doses. Forensic Science International, 170(2-3), 94-99. https://doi.org/10.1016/j.forsciint.2007.03.0231
- Shulgin, Alexander. (2005-05-03). DOB and Other Possible Prodrugs. Ask Dr. Shulgin Online. http://www.cognitiveliberty.org/shulgin/blg/2005/05/dob-and-other-possible-prodrugs.html1
- (1983). Diffuse Vascular Spasm Associated With 4-Bromo-2,5-Dimethoxyamphetamine Ingestion. https://doi.org/10.1001/jama.1983.0333035005302812
- Balikova M. (2005). Nonfatal and fatal DOB (2,5-dimethoxy-4-bromoamphetamine) overdose. 153(1), 85-91. https://doi.org/10.1016/j.forsciint.2005.04.022123
- Shulgin, A.T., Sargent, T., & Naranjo, C.. (1971). 4-Bromo-2,5-Dimethoxyphenylisopropylamine, a New Centrally Active Amphetamine Analog. Pharmacology, 5(2), 103-107. https://doi.org/10.1159/00013618112
- (1973). Controlled Substances Act Schedule I - Hallucinogenic Substances: 4-Bromo-2,5-dimethoxy-alpha-methylphenethylamine (4-bromo-2,5-DMA). Drug Enforcement Administration (DEA). https://isomerdesign.com/Cdsa/scheduleUS.php?schedule=1§ion=41
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Further Reading
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