2,5-Dimethoxy-4-iodoamphetamine

• DOI
• 1 - (4 -iodo-2 ,5- dimethoxyphenyl) -propan- 2-amine

• 42203-78-1 [( RS ) - ( ±)- hydrochloride ]
• 99665-05-1 [( S) - ( )- hydrochloride ]
• 82864-02-6 [( R) - ( -)- hydrochloride ]
• 64584-34-5 [( RS ) - ( ±)- Base ]
• 99665-04-0 [( S) - ( )- Base ]
• 82864-06-0 [( R) - ( -)- Base ]

White crystals ( hydrochloride)

• 321.15 g.mol -1 ( base)
• 357.62 g.mol -1 (hydrochloride)

Fixed

201 ° C ( hydrochloride)

Attention

Template: Infobox chemical / molecular formula search available

2,5-dimethoxy -4- iodamphetamin (abbreviated DOI ) is a research chemical, which is, on account of their structure to the substance groups of the substituted phenol ethers, and amphetamines. In neuroscience DOI is used as a radioligand for the study of 5 -HT2 serotonin receptors.

History

The American chemist Alexander Shulgin synthesized DOI for the first time and mentioned synthesis, dose and effect in his book PiHKAL. Various radionuclides of iodine were installed in DOI, the [ 125I ] -R -(-) - DOI was first developed by the American pharmacologists David E. Nichols.

Pharmacological properties

Pharmacokinetics

Shulgin gives the orally effective threshold dose for psychedelic effects with 600 micrograms, for the full psychedelic effect, a dose of 1.5-3 mg is given. The duration of action is 16-30 hours.

Effect

In high doses DOI acts of LSD, which was partly due to the action as an agonist at the serotonin receptors 5-HT2A/2C; the casting time is doubled, however. In cell experiments with psychedelic doses below the threshold dose, a potent anti-inflammatory effect was observed, with the DOI strongly inhibits tumor necrosis factor TNF- α over a longer period.

Legal status

• Germany