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User:WikiLinuz/Psychoactive substances/Classification of serotoninergic hallucinogens

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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-HT2A 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
TryptaminePhenethylamines
Substituted tryptamineErgoline2C-x25-NBMescaline
Unsubstituted

AMT: Rα—methyl; RN1,N2,4,5—H
DMT: RN1,N2—methyl; Rα,4,5—H
AET: Rα—ethyl; RN1,N2,4,5—H
DET: RN1,N2—ethyl; Rα,4,5—H
DPT: RN1,N2—propyl; Rα,4,5—H

DiPT: RN1,N2—isopropyl; Rα,4,5—H
4-Substituted

Psilocin: RN1,N2—methyl; Rα,4—H; R5—OH

4-HO-DiPT: RN1,N2—isopropyl; Rα,5—H; R4—OH
5-Substituted

5-MeO-DMT: RN1,N2—methyl; Rα,4—H; R5—methoxy

5-MeO-AMT: Rα—methyl; RN1,N2,4—H; R5—methoxy
LSA
R—H
LSD
R—ethyl
  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)