Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin

Sherwood, Alexander M.; Halberstadt, Adam L.; Klein, Adam K.; McCorvy, John D.; Kaylo, Kristi; Kargbo, Robert B.; Meisenheimer, Poncho

doi:10.1021/acs.jnatprod.9b01061

Cited by 51 publications

(78 citation statements)

References 34 publications

(76 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although psilocybin is the most popular and the most abundantly produced psychoactive compound/tryptamine derivative in magic mushrooms, other tryptamine derivatives such as psilocin [ 206 ], baeocystin [ 207 ], norbaeocystin [ 207 ], norpsilocin [ 207 ] ( Figure 6 ) and the beta-carbolines such as harmane and harmol [ 208 ], may also enhance the effects of psilocybin and the efficacy of psilocybin treatment [ 208 , 209 ]. Thus, it is likely that these hallucinogenic compounds may work in tandem to produce a synergistic effect [ 208 , 210 , 211 , 212 , 213 ].…”

Section: Psilocybin Synthesismentioning

confidence: 99%

The Therapeutic Potential of Psilocybin

Toyang²,

et al. 2021

View full text Add to dashboard Cite

The psychedelic effects of some plants and fungi have been known and deliberately exploited by humans for thousands of years. Fungi, particularly mushrooms, are the principal source of naturally occurring psychedelics. The mushroom extract, psilocybin has historically been used as a psychedelic agent for religious and spiritual ceremonies, as well as a therapeutic option for neuropsychiatric conditions. Psychedelic use was largely associated with the “hippie” counterculture movement, which, in turn, resulted in a growing, and still lingering, negative stigmatization for psychedelics. As a result, in 1970, the U.S. government rescheduled psychedelics as Schedule 1 drugs, ultimately ending scientific research on psychedelics. This prohibition on psychedelic drug research significantly delayed advances in medical knowledge on the therapeutic uses of agents such as psilocybin. A 2004 pilot study from the University of California, Los Angeles, exploring the potential of psilocybin treatment in patients with advanced-stage cancer managed to reignite interest and significantly renewed efforts in psilocybin research, heralding a new age in exploration for psychedelic therapy. Since then, significant advances have been made in characterizing the chemical properties of psilocybin as well as its therapeutic uses. This review will explore the potential of psilocybin in the treatment of neuropsychiatry-related conditions, examining recent advances as well as current research. This is not a systematic review.

show abstract

Section: Psilocybin Synthesismentioning

confidence: 99%

The Therapeutic Potential of Psilocybin

Toyang²,

et al. 2021

View full text Add to dashboard Cite

show abstract

“… 12 Until this year, there was no general synthetic method for producing useful amounts of the minor psychoactive tryptamines. 13 One of these minor components is aeruginascin, 14 the N -trimethyl analogue of psilocybin. Documented accounts of human exposure to Inocybe aeruginascens , a species of mushroom containing aeruginascin, describe hallucinations that exhibited only euphoric experiences.…”

Section: Introductionmentioning

confidence: 99%

Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity

Chadeayne¹,

Pham

Reid³

et al. 2020

ACS Omega

View full text Add to dashboard Cite

The putative active metabolite of aeruginascin, a naturally occurring tryptamine of “magic mushrooms,” has been synthesized and structurally characterized. Competitive radioligand binding assays demonstrate that it has a high affinity at human serotonin receptors 5-HT 1A , 5-HT 2A , and 5-HT 2B , though it does not bind at the 5-HT 3 receptor, where activity was previously predicted.

show abstract

“…This is the first instance of a synchronous biosynthesis of an active ingredient and the inhibitor of its degradation in a natural psychedelic species (Blei et al, 2020). Psilocin (4-hydroxy-N,N-dimethyltryptamine) is orally active in the absence of MAO inhibitors, indicating that the 4-hydroxy substitution makes the compound more resistant to deamination by MAO (Sherwood et al, 2020). The presence of -carbolines in 'magic mushrooms' and the varied activity of psilocin and DMT bring many questions forward on the nature of cooperative activity among chemicals in psychotropic natural products.…”

Section: Chemical Contextmentioning

confidence: 92%

DMT analogues: N-ethyl-N-propyltryptamine and N-allyl-N-methytryptamine as their hydrofumarate salts

Chadeayne¹,

Pham²,

Golen³

et al. 2020

Acta Cryst E

View full text Add to dashboard Cite

The solid-state structures of the hydrofumarate salts of two N,N-dialkyltryptamines, namely N-ethyl-N-propyltryptammonium (EPT) hydrofumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)propylazanium 3-carboxyprop-2-enoate}, C15H23N2 +·C4H3O4 −, and N-allyl-N-methyltryptammonium (MALT) hydrofumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)(prop-2-en-1-yl)azanium 3-carboxyprop-2-enoate}, C14H19N2 +·C4H3O4 −, are reported. Both compounds possess a protonated tryptammonium cation, and a hydrofumarate anion in the asymmetric unit. The ethyl group of the EPT cation is modeled as a two-component disorder with 50% occupancy for each component. In the extended structure, N—H...O and O—H...O hydrogen bonds generate infinite two-dimensional networks parallel to the (001) plane for both compounds.

show abstract

Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin

Cited by 51 publications

References 34 publications

The Therapeutic Potential of Psilocybin

The Therapeutic Potential of Psilocybin

Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity

DMT analogues: N-ethyl-N-propyltryptamine and N-allyl-N-methytryptamine as their hydrofumarate salts

Contact Info

Product

Resources

About