Identifying and isolating psychedelic compounds

While once considered taboo, magic mushrooms have recently experienced an increase in popularity and social acceptance.

This renaissance partly stems from new findings about the impact of psilocybin—and its dephosphorylated contemporary psilocin—on the 5-HT2A1-associated serotonin receptor.

New research has suggested that psychedelic compounds can activate this receptor, producing lasting results in patients struggling with depression, anxiety, post-traumatic stress disorder, and alcohol and drug abuse.2

As this body of scientific results increases, there has become an undeniable need for properly identifying and purifying this class of compounds.

It is important that separation is rapid and reliable, and administration of the compounds must be free of contaminates. Toxicological identification of these compounds is also essential for regulatory and safety purposes.

Psychedelics are typically perceived as being linked to feelings of well-being and connectedness.3

Hamilton Company has developed a methodology suitable for the isolation and identification of five common psychedelic compounds employed in disease treatment. Unlike many other methods currently available, the company has opted to isolate the compounds using hexylamine, an alkaline ion-pairing agent.

This eluent additive perfectly complements the PRP-1 stationary phase employed in the isolation.

In the example presented here, the use of the alkaline hexylamine as an eluent for the separation of five tryptamine derivatives demonstrated increased retention on the stationary phase versus acidic eluents while continuing to ensure good baseline resolution and peak shape.

The polymeric stationary phase remained robust under these conditions. There was no degradation of the stationary phase, even under 1,000 injections and over 92,000 column volumes. The peak shape and resolution were also found to be unaffected.

The separation between psilocybin and psilocin was completed over 4 minutes, delivering excellent resolution between the two molecules. It was also noted that investigation of the three later psychedelics was possible while maintaining baseline resolution and good peak symmetry.

Using the PRP-1 from Hamilton Company enables simple, straightforward identification and isolation of this class of molecules.

Chromatogram and compound results

Source: Hamilton Company

Column Information
Packing Material PRP-1, 5 µm
Dimensions 50 x 2.1 mm
P/N 79461
Chromatographic Conditions
Gradient 0.0–15.00 min., 5–35 % B
Temperature Ambient
Injection Volume 10 µL
Detection UV at 290 nm
Eluent A 0.1 % Hexylamine
Eluent B CH3CN + Eluent A
Flow Rate 1.0 mL/min

*-additional peaks are decomposition products from hydrolysis after extended injection number.

Compounds:

  1. 4-Phosphoryloxy-N,N-dimethyltryptamine (Psilocybin)
  2. 4-Hydroxy-N,N-dimethyltryptamine (Psilocin)
  3. 3,4-Methylenedioxymethamphetamine (MDMA)
  4. N,N-Dimethyltryptamine (DMT)
  5. Lysergic Acid Diethylamide (LSD)

Compounds: 1: 4-Phosphoryloxy-N,N-dimethyltryptamine (Psilocybin) 2: 4-Hydroxy-N,N-dimethyltryptamine (Psilocin) 3: 3,4-Methylenedioxymethamphetamine (MDMA) 4: N,N-Dimethyltryptamine (DMT) 5: Lysergic Acid Diethylamide (LSD)

Image Credit: Hamilton Company

Acknowledgments

Produced from materials originally authored by Adam L. Moore PhD. from Hamilton Company.

References and further reading

  1. Stebelska, K. F. Ther. Drug Monit. (2013), 35, 420–2.
  2. Nichols, D.E. Pharmacol. Ther. (2004), 101, 131–181.
  3. Gonzalez-Maeso, J.; Weisstaub, N.V.; Zhou, M.; Chan, P.; Ivic, L.; Ang, R.; Lira, A.; Bradley-Moore, M.; Ge, Y.; Zhou, Q.; et al. Neuron (2007), 53, 439–52.

About Hamilton Company

Hamilton — The Measure of Excellence

Hamilton Company specializes in the development, manufacturing and customization of precision measurement devices, automated liquid handling workstations, and sample management systems. Hamilton's processes are optimized for quality and flexibility. Whether it's a custom needle with a quick delivery time frame, a special length pH sensor, or a comprehensive solution to fully automate your assay workflow, trust that Hamilton products will always meet your needs.

Hamilton Company has been a leading global manufacturer for more than 60 years, with headquarters in Reno, Nevada; Franklin, Massachusetts; Timișoara, Romania; Bonaduz, Switzerland; and subsidiary offices throughout the world.


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Last updated: Oct 3, 2024 at 2:56 PM

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