2,5-dimethoxy-4-iodamphetamine

from Wikipedia, the free encyclopedia
Structural formula
Structure of the two enantiomers of 2,5-dimethoxy-4-iodamphetamine
( R ) shape (left) and ( S ) shape (right)
General
Surname 2,5-dimethoxy-4-iodamphetamine
other names
  • 1- (4-iodo-2,5-dimethoxyphenyl) -propan-2-amine ( IUPAC )
  • DOI
Molecular formula C 11 H 16 INO 2
Brief description

white crystals (hydrochloride)

External identifiers / databases
CAS number
  • 64584-34-5 [( RS ) - (±) -Base]
  • 99665-04-0 [( S ) - (+) - Base]
  • 82864-06-0 [( R ) - (-) - Base]
  • 42203-78-1 [( RS ) - (±) -hydrochloride]
  • 99665-05-1 [( S ) - (+) - hydrochloride]
  • 82864-02-6 [( R ) - (-) - hydrochloride]
PubChem 1229
ChemSpider 1192
Wikidata Q209251
properties
Molar mass
  • 321.15 g mol −1 (base)
  • 357.62 g mol −1 (hydrochloride)
Physical state

firmly

Melting point

201 ° C (hydrochloride)

solubility
  • Water: 10 mg / mL
  • Ethanol: 2 mg / mL
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,5-Dimethoxy-4-iodamphetamine (abbreviated DOI ) is a research chemical which, due to its structure, belongs to the phenol ethers and substituted amphetamines . In neuroscience , DOI is used as a radioligand to research the 5-HT 2 serotonin receptors .

history

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

Pharmacological properties

Pharmacokinetics

Shulgin gives the orally effective threshold dose for psychedelic effects as 600 µg. 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 has a similar effect to LSD , which is based, among other things, on its effect as an agonist on the serotonin receptors 5-HT 2A / 2C ; however, the casting time is doubled. In cell experiments with doses below the psychedelic threshold dose, a strong anti-inflammatory effect was observed, with the DOI strongly inhibiting the tumor necrosis factor TNF-α over a longer period of time.

Legal status

In Germany, DOI is a marketable , but not a prescription drug, because it is listed in Appendix II BtMG .

See also

literature

  • Alexander Shulgin, Ann Shulgin: PiHKAL - A Chemical Love Story Transform Press, ISBN 0-9630096-0-5 .

Web links

Individual evidence

  1. ↑ a b c d PiHKAL # 67 DOI
  2. ↑ a b c d data sheet (±) -DOI hydrochloride from Sigma-Aldrich , accessed on December 12, 2011 ( PDF ).
  3. ↑ Gisela Braun, Alexander T. Shulgin, Thornton Sargent III: Synthesis of 123 I-labeled 4-iodo-2,5-dimethoxyphenylisopropylamine . In: Journal of Labeled Compounds and Radiopharmaceuticals . 14, No. 5, 1978, pp. 767-773. doi : 10.1002 / jlcr.2580140515 .
  4. ↑ Pablo R. Moya, Kelly A. Berg, Manuel A. Gutiérrez-Hernandez, Patricio Sáez-Briones, Miguel Reyes-Parada, Bruce K. Cassels, William P. Clarke: Functional Selectivity of Hallucinogenic Phenethylamine and Phenylisopropylamine Derivatives at Human 5- Hydroxytryptamine (5-HT) 2A and 5-HT 2C Receptors , in: Journal of Pharmacology and Experimental Therapeutics , 2007 , 321 (3) , 1054-1061; doi : 10.1124 / jpet.106.117507 .
  5. ↑ Bangning Yu, Jaime Becnel, Mourad Zerfaoui, Rasika Rohatgi, A. Hamid Boulares and Charles D. Nichols: Serotonin 5-Hydroxytryptamine2A Receptor Activation Suppresses Tumor Necrosis Factor-α-Induced Inflammation with Extraordinary Potency . In: Journal of Pharmacology and Experimental Therapeutics . 327, No. 2, 2008, pp. 316-323. doi : 10.1124 / jpet.108.143461 . PMID 18708586 .