2,5-dimethoxy-4-iodoamphetamine

DOI
Chemical name	1-(2,5-dimethoxy-4-iodophenyl)- propan-2-amine
Chemical formula	C11H6INO2
Molecular mass	321.15 g/mol
Melting point	201 °C (hydrochloride)
CAS numbers	64584-34-5, 82830-53-3, 82864-06-0, 99665-04-0
SMILES	N[C@H](C)CC1=C(OC)C=C(I)C(OC)=C1 (R-isomer)

DOI or 2,5-dimethoxy-4-iodoamphetamine is a psychedelic hallucinogenic drug 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. [¹²⁵I]-R-(-)-DOI is used as a radioligand. DOI is active at a dosage of 1.5 - 3.0 mg and has an extremely long duration of 16 - 30 hours.

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 receptor.

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.

See also

• DOM
• DOB
• PiHKAL

External references

• Erowid about DOI
• The Lycaeum about DOI
• TiHKAL entry

Categorization