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DOI
IUPAC name	1-(2,5-dimethoxy-4-iodophenyl)- propan-2-amine
Identifiers
CAS number	64584-34-5, 82830-53-3, 82864-06-0, 99665-04-0, 82864-02-6
SMILES	N[C@H](C)CC1=C(OC)C=C(I)C(OC)=C1 (R-isomer)
Properties
Molecular formula	C11H16INO2
Molar mass	321.15 g/mol
Melting point	201 °C (hydrochloride)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

DOI or 2,5-dimethoxy-4-iodoamphetamine is a psychedelic drug and a substituted amphetamine of the phenethylamine family. Despite being a substituted amphetamine it is not 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-HT_2A serotonin receptors. When ingested recreationally, DOI is active at a dosage of 1.5 - 3.0mg (orally) and has a duration of 16 - 30 hours (approximately twice as long as LSD). 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. It is often 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. Unlike LSD, the psychedelic amphetamines (including DOI) can have harmful and potentially fatal physical effects in overdose. Although there have been no known deaths due to DOI ingestion, it is relatively new on the recreational scene so long-term effects are not known.

Pharmacology

The hallucinogenic effect of DOI is mediated by its partial agonistic activity at the 5-HT_2A serotonin receptor, but DOI also has a high binding affinity for the 5-HT_2B and the 5-HT_2C serotonin receptors. DOI is often used as a tool compound in research when studying the 5-HT₂ receptor family. The solubility of DOI hydrochloride in H₂O is 10 mg/ml, and in ethanol 2 mg/ml ¹.

History

DOI was first synthesized by Alexander Shulgin. The radioactive iodine-125 form of DOI was first developed in the lab of David E. Nichols. In January 2007, British Police reported that 3 young men had taken ill, reportedly, after taking DOI at a rave in Biggleswade, near Milton Keynes, and warned others who had taken it to seek medical attention. This would appear to be the first indication that DOI has found more widespread use as a recreational drug in the UK. ²

See also

• DOM
• DOB
• PiHKAL

References

External links

• Erowid about DOI
• The Lycaeum about DOI
• PiHKAL entry

Categorization

Wikipedia content modification information:

• This page was last modified on 19 November 2008, at 00:24.

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