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2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike many other substituted amphetamines, however, it is not primarily a stimulant. DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer. In neuroscience research, [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of 5-HT2A serotonin receptors. DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience. The after effects include residual stimulation and difficulty sleeping, which, depending on the dose, may persist for days. While rare, it is sometimes sold as a s

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dbo:abstract
  • 2,5-Dimethoxy-4-iodamphetamin (abgekürzt DOI) ist eine Forschungschemikalie, die aufgrund ihrer Struktur zu den Stoffgruppen der Phenolether und zu den substituierten Amphetaminen zählt.In den Neurowissenschaften wird DOI als Radioligand zur Erforschung der 5-HT2-Serotoninrezeptoren verwendet. (de)
  • 2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike many other substituted amphetamines, however, it is not primarily a stimulant. DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer. In neuroscience research, [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of 5-HT2A serotonin receptors. DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience. The after effects include residual stimulation and difficulty sleeping, which, depending on the dose, may persist for days. While rare, it is sometimes sold as a substitute for LSD, or even sold falsely as LSD, which may be dangerous because DOI does not have the same established safety profile as LSD. (en)
  • 2,5-Dimetoksy-4-jodoamfetamina, DOI – związek jodoorganiczny, psychodeliczna substancja psychoaktywna, pochodna fenyloetyloaminy. Po raz pierwszy została otrzymana przez amerykańskiego chemika Alexandra Shulgina. (pl)
  • 4-Jod-2,5-dimetoxiamfetamin eller DOI (av 2,5-dimethoxy-4-iodoamphetamine) är en psykedelisk drog ur fenetylamin-familjen, som först syntetiserades av Alexander Shulgin. Substansen är narkotikaklassad och ingår i förteckning I i Sverige. Samma sak gäller kloranalogen till DOI, (DOC). Den närbesläktade (icke-joderade) substansen (DMA) ingår även i förteckning P II i 1971 års psykotropkonvention. (sv)
  • 2,5-диметокси-4-иодамфетамин (DOI) — химическое соединение класса амфетаминов. Психоделик, агонист 5-HT2A-рецепторов. Типичная оральная доза составляет 1,5—3 мг, продолжительность действия — 16—30 ч. (ru)
dbo:iupacName
  • 1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine (en)
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  • 2,5-Dimethoxy-4-iodamphetamin (abgekürzt DOI) ist eine Forschungschemikalie, die aufgrund ihrer Struktur zu den Stoffgruppen der Phenolether und zu den substituierten Amphetaminen zählt.In den Neurowissenschaften wird DOI als Radioligand zur Erforschung der 5-HT2-Serotoninrezeptoren verwendet. (de)
  • 2,5-Dimetoksy-4-jodoamfetamina, DOI – związek jodoorganiczny, psychodeliczna substancja psychoaktywna, pochodna fenyloetyloaminy. Po raz pierwszy została otrzymana przez amerykańskiego chemika Alexandra Shulgina. (pl)
  • 4-Jod-2,5-dimetoxiamfetamin eller DOI (av 2,5-dimethoxy-4-iodoamphetamine) är en psykedelisk drog ur fenetylamin-familjen, som först syntetiserades av Alexander Shulgin. Substansen är narkotikaklassad och ingår i förteckning I i Sverige. Samma sak gäller kloranalogen till DOI, (DOC). Den närbesläktade (icke-joderade) substansen (DMA) ingår även i förteckning P II i 1971 års psykotropkonvention. (sv)
  • 2,5-диметокси-4-иодамфетамин (DOI) — химическое соединение класса амфетаминов. Психоделик, агонист 5-HT2A-рецепторов. Типичная оральная доза составляет 1,5—3 мг, продолжительность действия — 16—30 ч. (ru)
  • 2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike many other substituted amphetamines, however, it is not primarily a stimulant. DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer. In neuroscience research, [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of 5-HT2A serotonin receptors. DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience. The after effects include residual stimulation and difficulty sleeping, which, depending on the dose, may persist for days. While rare, it is sometimes sold as a s (en)
rdfs:label
  • 2,5-Dimethoxy-4-iodamphetamin (de)
  • 2,5-Dimethoxy-4-iodoamphetamine (en)
  • 2,5-Dimetoksy-4-jodoamfetamina (pl)
  • 2,5-Диметокси-4-иодамфетамин (ru)
  • 4-Jod-2,5-dimetoxiamfetamin (sv)
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  • DOI (en)
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