4-Bromo-2,5-Dimethoxyphenylisopropylamine, a New Centrally Active Amphetamine Analog

Shulgin, Alexander T.; Sargent, T.; Naranjo, Claudio A.

doi:10.1159/000136181

Cited by 56 publications

(35 citation statements)

References 9 publications

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“…MMDA appears to share the properties of mood-intensification, feelingenhancement and minimal sensory distortion previously described for MDA (8) and 4-bromo-2,5-dimethoxyphenyiisopropylamine (19). We suggest that these compounds represent a new class of psychopharmacologic agents, distinct from the psychotomimetics, which deserve further investigation as useful drugs in treatment of neuroses.…”

Section: Discussionsupporting

confidence: 55%

Animal Pharmacology and Human Psychopharmacology of 3-Methoxy-4,5-Methylenedioxyphenylisopropylamine (MMDA)

Shulgin¹,

Sargent²,

Naranjo³

1973

Pharmacology

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A rationale is presented for the investigation of the synthesis and pharmacology of 3-methoxy-4,5-methylenedioxyphenyl isopropylamine (MMDA) as a potential psychodysleptic compound; these experiments are reported. The chemical synthesis and physical properties of this compound are described. The pharmacologic effects of MMDA in several animal species are presented, as are its clinical effects in man. The animal pharmacology was generally unremarkable, except for a hypotensive effect in the dog, and the therapeutic index (LD₅₀ rat/MED₅₀ human) was 85. The subjective effects of MMDA in man include an enhancement of feeling and of eyes-closed visual imagery, but no hallucinogenesis or other disturbance of the sensorium. Reality testing and environmental contact are not affected except for a tendency to withdraw into a state of drowsiness, or into a world of fantasy and visual imagery. The induced state of increased availability of emotion was easily manipulated in the psychotherapeutic setting used, and appeared to lead to an enhanced insight into subconscious content.

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Section: Discussionsupporting

confidence: 55%

Animal Pharmacology and Human Psychopharmacology of 3-Methoxy-4,5-Methylenedioxyphenylisopropylamine (MMDA)

Shulgin¹,

Sargent²,

Naranjo³

1973

Pharmacology

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“…DOB psychoactive effect is mediated via 5HT 2A/2C receptors interaction in the central nervous system [4,5] and is similar to that exhibited by other hallucinogenic phenylalkylamines, for example, mescalin [6,7]. A clinical human study [8] found that 2 mg oral dose of DOB produced emotional stimulation, perceptual enhancement, but not www.elsevier.com/locate/forsciint Forensic Science International 170 (2007) [94][95][96][97][98][99] perceptual distortions or hallucinations. However, uncontrolled illegal use of potential higher doses may lead to hallucinations, panic state, vasospasms, coma, and even death [1,[9][10][11].…”

Section: Introductionmentioning

confidence: 87%

Distribution profile of 2,5-dimethoxy-4-bromoamphetamine (DOB) in rats after oral and subcutaneous doses

Beránková

Szkutová

Balı́ková

2007

Forensic Science International

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“…Of the 2,5-dimethoxy-4 series of substituted amphetamine hallucinogens, synthesis of DOM was reported first in the scientific literature in 1970, [12] followed later by DOB, [13] and DOI. [14] In their recent book, however, Shulgin et al .…”

Section: A Brief Chemistry and Timeline Of Doimentioning

confidence: 99%

Head‐twitch response in rodents induced by the hallucinogen 2,5‐dimethoxy‐4‐iodoamphetamine: a comprehensive history, a re‐evaluation of mechanisms, and its utility as a model

Canal

Morgan

2012

Drug Testing and Analysis

182

200

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Two primary animal models persist for assessing hallucinogenic potential of novel compounds and for examining the pharmacological and neurobiological substrates underlying the actions of classical hallucinogens, the two-lever drug discrimination procedure and the drug-induced head-twitch response (HTR) in rodents. The substituted amphetamine hallucinogen, serotonin 2 (5-HT2) receptor agonist, 2,5-dimethoxy-4-iodoamphetamine (DOI) has emerged as the most popular pharmacological tool used in HTR studies of hallucinogens. Synthesizing classic, recent, and relatively overlooked findings, addressing ostensibly conflicting observations, and considering contemporary theories in receptor and behavioural pharmacology, this review provides an up-to-date and comprehensive synopsis of DOI and the HTR model, from neural mechanisms to utility for understanding psychiatric diseases. Also presented is support for the argument that, although both the two-lever drug discrimination and the HTR models in rodents are useful for uncovering receptors, interacting proteins, intracellular signalling pathways, and neurochemical processes affected by DOI and related classical hallucinogens, results from both models suggest they are not reporting hallucinogenic experiences in animals.

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4-Bromo-2,5-Dimethoxyphenylisopropylamine, a New Centrally Active Amphetamine Analog

Cited by 56 publications

References 9 publications

Animal Pharmacology and Human Psychopharmacology of 3-Methoxy-4,5-Methylenedioxyphenylisopropylamine (MMDA)

Animal Pharmacology and Human Psychopharmacology of 3-Methoxy-4,5-Methylenedioxyphenylisopropylamine (MMDA)

Distribution profile of 2,5-dimethoxy-4-bromoamphetamine (DOB) in rats after oral and subcutaneous doses

Head‐twitch response in rodents induced by the hallucinogen 2,5‐dimethoxy‐4‐iodoamphetamine: a comprehensive history, a re‐evaluation of mechanisms, and its utility as a model

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