User:WikiLinuz/Psychoactive substances/Classification of serotoninergic hallucinogens

Psychedelics (also serotoninergic hallucinogens) are divided into two main groups based on chemical structure: indoleamines (also indolealkylamines; example, ergolines, including LSD and its analogs, tryptamines, such as N,N-DMT and 5-MeO-DMT) and phenylalkylamines. Phenylalkylamines are highly selective for serotonin 5-HT₂ receptors, while indoleamines are relatively non-selective for 5-HT receptors, displaying moderate to high affinity to 5-HT₁ and 5-HT₂ receptor subtypes.

Phenylalkylamines can further be divided into two subgroups: phenylisopropylamines (analogs of amphetamine; example, DOB and DOM) and phenethylamines (example, mescaline, 2C-x and derivatives).

Prototype of 2C-x series, 2C-B, was first synthesized by Shulgin in 1974; since 2010, a new group of 2C compounds containing an N-(2-methoxy)benzyl (N-benzoylmethoxy) substituent, known as N-(2-methoxybenzyl)phenethylamines (that is, 25x-NBx, 25x-NBOM, or NBOM) has emerged. Structure-activity studies shown that this substituent significantly increases affinity towards 5-HT_2A receptor and its pharmacological activity.

The first of NBOMes was 25B-NBOMe (later 25I-NBOMe and 25C-NBOMe). Since then, potent NBOMes were synthesized by exchanging iodine atom in 25I-NBOMe for other halogens, example, bromine 25B-NBOMe, chlorine 25C-NBOMe, hydrogen 25H-NBOMe, nitro group 25N-NBOMe, or an organic functional group, -methyl 25D-NBOMe, -ethyl 25E-NBOMe, -isopropyl 25iP-NBOMe.
— Jolanta Z, Monika K, and Piotr A (26 February 2020). "NBOMes–Highly Potent and Toxic Alternatives of LSD". Frontiers in Neuroscience. 14: 2. doi:10.3389/fnins.2020.00078.{{cite journal}}: CS1 maint: unflagged free DOI (link)

General classification of serotoninergic hallucinogens based on chemical structure^[1]^[2]

Serotoninergic hallucinogens

Tryptamine

Phenethylamines

Substituted tryptamine

Ergoline

2C-x

25-NB

Mescaline

Unsubstituted

AMT: R_α—methyl; R_N1,N2,4,5—H
DMT: R_N1,N2—methyl; R_α,4,5—H
AET: R_α—ethyl; R_N1,N2,4,5—H
DET: R_N1,N2—ethyl; R_α,4,5—H
DPT: R_N1,N2—propyl; R_α,4,5—H

DiPT: R_N1,N2—isopropyl; R_α,4,5—H

4-Substituted

Psilocin: R_N1,N2—methyl; R_α,4—H; R₅—OH

4-HO-DiPT: R_N1,N2—isopropyl; R_α,5—H; R₄—OH

5-Substituted

5-MeO-DMT: R_N1,N2—methyl; R_α,4—H; R₅—methoxy

5-MeO-AMT: R_α—methyl; R_N1,N2,4—H; R₅—methoxy

LSA
R—H

LSD
R—ethyl

^ Daniela C, Felix C, Anca OD (2021). "Toxicity of psychedelic drugs". Toxicological Risk Assessment and Multi-System Health Impacts from Exposure. Academic Press. pp. 545–556. doi:10.1016/B978-0-323-85215-9.00022-2. ISBN 978-0-323-85215-9.
^ Jolanta Z, Monika K, and Piotr A (26 February 2020). "NBOMes–Highly Potent and Toxic Alternatives of LSD". Frontiers in Neuroscience. 14: 1-12. doi:10.3389/fnins.2020.00078.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[1] Daniela C, Felix C, Anca OD (2021). "Toxicity of psychedelic drugs". Toxicological Risk Assessment and Multi-System Health Impacts from Exposure. Academic Press. pp. 545–556. doi:10.1016/B978-0-323-85215-9.00022-2. ISBN 978-0-323-85215-9.

[2] Jolanta Z, Monika K, and Piotr A (26 February 2020). "NBOMes–Highly Potent and Toxic Alternatives of LSD". Frontiers in Neuroscience. 14: 1-12. doi:10.3389/fnins.2020.00078.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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