2,5-Dimethoxy-4-iodoamphetamine

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DOI
Chemical name	1-(2,5-dimethoxy-4-iodophenyl)- propan-2-amine
Chemical formula	C₁₁H₁₆INO₂
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. DOI is used recreationally, and is often confused with LSD by unexperienced users. However, the trip is somewhat more energetic than an LSD trip, and often the visuals are less intense. The after effects include a difficulty getting to sleep and communicating. Depending on the amount taken, these symptoms may persist for days.

1 Pharmacology
2 History
3 See also
4 External references
5 Categorization

[edit] 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. The solubility of DOI-hydrochloride in H2O is 10 mg/ml, and in ethanol 2 mg/ml (source: www.sigmaaldrich.com MSDS)

[edit] 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.

[edit] See also

[edit] External references

[edit] Categorization

Hallucinogenic phenethylamines edit
2C-B, 2C-B-FLY, 2C-C, 2C-D, 2C-E, 2C-G, 2C-I, 2C-N, 2C-O, 2C-O-4, 2C-P, 2C-T, 2C-T-2, 2C-T-4, 2C-T-7, 2C-T-8, 2C-T-9, 2C-T-21, 2C-TFM, 3C-E, 3C-P, Br-DFLY, DESOXY, DMMDA-2, DOB, DOC, DOET, DOI, DOM, DON, Escaline, Isoproscaline, Lophophine, MDA, MMDA, Macromerine, Mescaline, Proscaline, TMA