Designer Drug Exposé: Tryptamine Psychedelics
The tryptamines brought us DMT and psilocybin — but this is only the tip of the iceberg. The sheer variety of psychedelic molecules in this chemical group is astonishing.
Most of what we consider "classical psychedelics" fall into the tryptamine family. This includes psilocybin, psilocin, and DMT.
Exceptions include mescaline (from San Pedro and Peyote), MDMA, and 2C-B, which are classified instead as phenethylamines (coming in part 3). LSD and other lysergamides are coming in part 4.
Everything from Bufo toad venom, magic mushrooms, ayahuasca, and iboga owe their psychedelic effects to tryptamine psychedelics.
All of the tryptamines listed above, with the exception of ibogaine, are universally banned. Ibogaine is banned in the US and listed as a prescription drug in Canada and Brazil — but is largely unregulated in the rest of the world.
Arguably, the first designer tryptamine was AMT (alpha-methyltryptamine) — which was invented by Upjohn in the 1960s as an antidepressant. It was discontinued but later revived and used as an entry point for designer drug manufacturers searching for “legal” alternatives to DMT and psilocybin in the ‘80s and ‘90s.
Today, there are hundreds, if not thousands, of designer drugs in the tryptamine family. Many are modeled after psilocybin/DMT (N-methylated tryptamines) — but there are also a few newer groups, such as the n-allyated tryptamines, the alpha-methylated tryptamines, and ibogaine analogs. We cover all of these groups in this article.
From the long list of designer tryptamines we’ll cover below, here are 5 that stand out the most:
4-AcO-DMT — The most popular psilocin prodrug. Its effects are virtually indistinguishable from magic mushrooms.
4-AcO-MET — This compound is similar to psilocin but has a history of producing a more "comfortable" headspace and trippy visuals.
4-HO-DiPT — A psilocin homolog with short action (1-2 hours), rapid onset of effects (~15 minutes) and powerful psychedelic qualities in doses as low as 15 mg.
DiPT — A unique tryptamine that has a minimal visual effect but pronounced auditory hallucinations.
5-MeO-AMT — A potent psychedelic tryptamine with an amphetamine component similar to MDMA (ecstasy).
What Are Tryptamine Psychedelics?
Tryptamines are compounds that feature an indole ring and an amine functional group.
The chemical structure of tryptamines closely resembles the neurotransmitter serotonin. By mimicking this neurotransmitter and binding to places like the 5HT2A receptors, tryptamine psychedelics modulate the brain's signaling pathways — resulting in profound alterations in consciousness and sensory perception.
The effects of these compounds vary significantly, but the general effects share a similar theme. Visual, auditory, and tactile perception are dramatically altered, but new sensory information is not created. Elements in one’s perceptual field are merely reinterpreted or transformed.
Strong psychedelics, like 5-MeO-DMT and N,N,DMT, often lead to profound out-of-body mystical experiences and ego-dissolution. Milder psychedelics, like the many psilocin prodrugs, the alpha-methylated tryptamines, or N-allyated tryptamines can have profound introspective effects too — but are less likely to push users into a state of complete ego dissolution.
Naturally-Occurring Tryptamine Psychedelics
Most of the designer drugs we have today were inspired by the tryptamines produced by various plants, fungi, and animals.
Ayahuasca, for example, is a combination of two plants — Banisteriopsis caapi (source of harmala alkaloids) and one of the many plants that contain DMT. The selection of plant-based DMT varies by region and tradition, but common examples include chacruna (Psychotria viridis) or mimosa (Mimosa pudica).
The Bufo alvarius toad also produces psychedelic tryptamines in the venom glands on its back. It makes 5-MeO-DMT, as well as bufotenin and a variety of other trace tryptamines, several of which are believed to be psychedelic.
Psilocybin mushrooms, such as Psilocybe cubensis, Psilocybe semilanceata, and dozens of other species of magic mushrooms produce psilocin, psilocybin, and baeocystin.
List of naturally occurring psychedelic tryptamines:
5-Bromo-DMT
5-MeO-DMT
5-MeO-NMT
Bufotenin (5-HO-DiPT)
Baeocystin (4-HO-NMT)
N,N,DMT
Psilocybin (4-PO-DMT)
Psilocin (4-HO-DMT)
Legal Status of Tryptamine Psychedelics
LSD was the first psychedelic to get banned by the United States. This happened in 1966. Within just a few years, many other psychedelics, including several tryptamines (DMT, psilocin, and psilocybin), as well as various phenethylamines (mescaline first, followed a few years later with MDMA and 2C-B), were banned under the Controlled Substances Act of 1970. This ban also included psychoactive plants like marijuana and many opioids.
The UN Convention on Psychotropic Substances was established a year later, in 1971. This convention maintained a worldwide ban on all of the classical tryptamine psychedelics known up to that point. Many others have been added in the decades that followed.
Universally banned tryptamines include:
5-MeO-DIPT (also 5-MeO-DPT as recognized isomer)
5-MeO-DMT
AMT
Bufotenine
DET (also MiPT as recognized isomer)
DMT
Psilocin
Psilocybin
Despite the invention of countless new tryptamines within the past two decades, the DEA has had a difficult time placing new psychedelics into the Schedule I grouping in recent years.
For example, in 2022, the DEA tried (and failed) to ban five designer tryptamine psychedelics — 4-HO-DiPT, 5-MeO-AMT, 5-MeO-MiPT, 5-MeO-DET, and DiPT.
On the contrary, many US jurisdictions have been slowly moving in the opposite direction, with states like Colorado and Washington decriminalizing psychedelic substances. Oregon recently legalized natural tryptamine-based psychedelics and established a framework for supervised therapeutic use of psilocybin.
Religious exemptions have also been granted for psychedelics like ayahuasca (União do Vegetal and Santo Daime) and peyote (Native American Church).
DMT Analogs
When people talk about “DMT,” they usually mean either N,N,DMT or 5-MeO-DMT. However, there are actually a few key psychedelics in this group. Psilocybin and psilocin — the active ingredients in magic mushrooms — are also forms of DMT (4-PO-DMT and 4-HO-DMT, respectively).
The acronym “DMT” stands for “dimethyltryptamine” — which means there are two methyl groups (CH3) within the amine. Chemists can play around with this amine to create totally new psychedelics.
A few designer drug examples that contain dimethyltryptamine include 4-AcO-DMT, 4-MeO-DMT, 4,5-DHP-DMT, 5-Chloro-DMT, 5-Ethoxy-DMT, 5-Fluoro-DMT, 7,N,N-DMT, and 4-MeO-DMT.
Alterations to the amide group change the name from "DMT" to something else.
Here are a few examples of designer DMT analogs differentiated by amide group:
DBT (dibutyl) — 5-MeO-DBT
DET (di-ethyl) — 5-Fluoro-DET, 6-Fluoro-DET
DiPT (di-iso-propyl) — 5-HO-DiPT, 5-MeO-DiPT, and 4-HO-DiPT
DMT (dimethyl) — 4-AcO-DMT, 4-MeO-DMT, 4,5-DHP-DMT, 5-Bromo-DMT, 5-Chloro-DMT, 5-Ethoxy-DMT, 5-Ethyl-DMT, 5-Fluoro-DMT, 6-Fluoro-DMT, 7,N,N-DMT, and DMT-N-Oxide
DPT (di-propyl) — 4-AcO-DPT and 4-HO-DPT
DSBT (di-sec-butyl) — 4-HO-DSBT
EPT (propyl) — 4-HO-EPT and 5-Fluoro-EPT
MET (ethyl) — 5-Fluoro-MET, 5-MeO-MET, 7F-5-MeO-MET, 4-AcO-MET
MiPT (methyl-isopropyl) — 5-MeO-MiPT
MPT (methylpropyl) — 4-HO-MPT
NMT (methyl) — 5-MeO-NMT
PiPT (propyl-isopropyl) — 4-HO-PiPT
Pyr-T (tetramethylene) — 4-HO-pyr-T
NOTE: New, equally creative modifications to this portion of the molecule are made all the time, so this list is far from comprehensive.
The effects of different DMT-analogs differ significantly from one compound to another — even the classics, N,N,DMT and 5-MeO-DMT produce distinct psychedelic experiences.
N,N,DMT is known for being very visual and geometric — while 5-MeO-DMT can be described as more “mystical” but less kaleidoscopic in terms of visual experience.
Psilocin from magic mushrooms (4-HO-DMT) is milder and less out-of-body than both N,N,DMT and 5-MeO-DMT but still targets the same receptors and produces similar altered states of consciousness as lower-level 5-MeO or N,N,DMT.
Many tryptamines are inactive. Some, like psilocybin (4-PO-DMT), become active after ingesting them by being converted to an active form by the liver (psilocybin is converted to the active form, psilocin). Other compounds remain inactive or offer only mild psychoactivity. Examples include 5-bromo-DMT (SpongeBob DMT) or 5-MeO-NMT.
Psilocin (4-HO-DMT) Analogs
Psilocin features the same dimethylated tryptamine (DMT) as N,N,DMT and 5-MeO-DMT — the only difference is that it contains a hydroxy group on the fourth carbon of the indole ring (4-HO).
Both psilocin and its naturally occurring prodrug, psilocybin, are included on the UN's list of controlled substances.
Alterations to the psilocin base structure can be made to either the ethylamine chain or the amide group (DMT). These changes usually maintain similar psychoactive effects in the new psilocin-based designer drugs.
Compounds like 4-HO-DiPT are reported by the psychedelic late chemist and esteemed psychonaut Alexander Shulgin to be even stronger than psilocin and feature a rapid onset time of just 15 minutes (orally).
Designer drugs that share close similarities to psilocin include 4-AcO-DMT (most popular), 1-methylpsilocin, 4-AcO-DPT, 4-HO-DPT (inactive), 4-HO-DET (inactive), 4-HO-DSBT, 4-HO-EPT, 4-HO-MPT, 4-HO-PiPT, 4-HO-pyr-T (described as “bizzarre” by Shulgin), 4-HO-MALT, 4-HO-MiPT (strong), and 4-HO-DiPT (very strong).
In terms of subjective effects, the closest designer drugs to psilocin include various produgs like 4-AcO-DMT, 4-MeO-DMT, 4-HO-MET, and 4-AcO-DET — all of which produce effects that are virtually indistinguishable from magic mushrooms.
5-MeO-DMT Analogs
This powerful psychedelic features the same base structure as N,N,DMT but with the addition of a methoxy group on the fifth carbon of the central indole ring (5-MeO).
This compound is found naturally in the Colorado River toad (Bufo alvarius) as well as several species of plants, including Anadenanthera peregrina (yopo), Anadenanthera colubrina, and various species of Virola.
Designer tryptamines that most closely emulate the effects of 5-MeO-DMT include 5-MeO-DiPT (Foxy Methoxy), 5-MeO-DALT (Foxtrot), 5-MeO-AMT, and 5-MeO-MiPT.
Other analogs include 5-Ethoxy-DMT, 5-HO-DiPT, 5-MeO-DBT, 5-MeO-DiPT, 5-MeO-MET, 5-MeO-NBpBrT, 5-MeO-NMT, 5-MeO-PiPT, 5,7-Dihydroxytryptamine, 7F-5-MeO-MET, bufotenidine, and HIOC.
4-Hydroxy-5-methoxydimethyltryptamine (AKA psilomethoxin) is essentially a combination of psilocin and 5-MeO-DMT — featuring both compounds’ functional groups on the 4th and 5th carbons of the central indole ring.
N,N,DMT Analogs
N,N,DMT is the most basic of the dimethylated tryptamines. It features all the generic aspects of a tryptamine, with two methyl groups attached to the terminal nitrogen atom.
N,N,DMT is explicitly included in the UN Convention on Psychotropic Substances and is the active psychedelic ingredient in ayahuasca, changa, and yopo.
The closest designer drugs to N,N,DMT (in terms of subjective effects) are DPT (N,N-dipropyltryptamine), EPT (ethylpropyltryptamine), and MALT (N-methyl-N-allyltryptamine).
DMT-N-Oxide is an inactive form of N,N,DMT that was sold as a DMT-alternative designer drug for a while.
Alpha-Methylated Tryptamines
This group is usually connotated by either an “AMT” or “AET” in the name. For example, 5-MeO-AMT, 6-Fluoro-AMT, 7-Chloro-AMT, AL-37350A (4,5-DHP-AMT), 7-Me-AET (7-Methyl-α-ethyltryptamine), and 4-Me-αET (4-Methyl-α-ethyltryptamine).
Th alpha-methylated tryptamines are differentiated from N-methylated tryptamines by the location of their functional group. Instead of attaching to the terminal nitrogen, they’re attached to the carbon directly before the nitrogen (the alpha position).
This subtle difference gives them a subtle “amphetamine-like” quality, and even looks like an amphetamine with an additional pyrazole ring. The alpha-methylated tryptamines tend to be more stimulating and appear to interact more with dopaminergic systems than other tryptamines.
5-MeO-AMT is a very potent member of this group — with effects often compared to a candy flip (LSD + MDMA). It’s usually taken orally and is active in doses as low as 3 mg and shows signs of toxicity in doses over just 6 mg.
N-Allyated Tryptamines
N-allylated tryptamines are differentiated by the presence of an allyl group. The compounds in this family tend to be less psychedelic than other tryptamines. For example, 5-MeO-DALT (AKA “Foxtrot”) has more of a body high than anything else, and the visuals from 4-HO-MALT have been described as “nice, but forgettable.”
The first member of this group was 5-MeO-DALT, which was created by Alexander Shulgin in his lab sometime in the early 2000s. It was first reported on the designer drug market in 2007. 4-AcO-DALT didn’t appear until 2012, and 4-HO-MALT in 2021.
There are a few different types here, depending on which allyl group is attached:
DALT — 4-AcO-DALT, 5-MeO-DALT (Foxtrot)
MALT — 4-HO-MALT
ALiPT — N-Allyl-N-isopropyltryptamine
There are a few members of this group that overlap with other groups, such as 4-HO-MALT with psilocin and 5-MeO-DALT with 5-MeO-DMT.
Ibogaine Analogs
Ibogaine technically classifies as a tryptamine — but the effects are distinct from basically every other member of the family. The effects of ibogaine can be described as dissociative and oneriogenic with stimulant-like properties.
While most tryptamines rely on their ability to mimic serotonin and bind to the 5HT2A and other serotonin receptors, ibogaine acts more like ketamine — blocking the NMDA (N-methyl-D-aspartate) receptors to produce a dissociative action. Ibogaine only has a weak interaction with the 5HT2A receptors.
Ibogaine also binds to the kappa-opioid receptors, which is the same mechanism of action used by salvinorin-A (Salvia divinorum) to produce its distinct and bizarre flavor of psychedelia. Its effects also owe to a subtle interaction with the nicotinic and sigma receptors.
Ibogaine is not universally banned. In places like Canada and Brazil, it's classified as a prescription medication. It's explicitly banned in countries including the United States, New Zealand, Norway, the United Kingdom, and Sweden.
Most other countries don’t offer any regulatory guidance for ibogaine — allowing the formation of a booming industry around ibogaine therapy and iboga retreat centers.
As far as designer drugs go, there isn’t much available for ibogaine (yet) — this is largely due to a complex pharmacological profile and synthesis process.
One non-psychoactive ibogaine analog, called 18-MC (18-methoxycoronaridine), is currently under development by MindMed. This compound is suggested to offer comparable anti-addictive qualities to ibogaine but doesn't produce its distinct psychedelic actions.
Other synthetic analogs that haven’t been thoroughly explored include 18-MAC (18-methylaminocoronaridine) and ME-18-MC (2-methoxyethyl-18-methoxycoronaridinate).
Designer Drug Series
Part 2: Tryptamine Designer Drugs
Part 8: Sedative Hypnotics & Opioids (Subscribe)
Part 9: Deliriants (Subscribe)
Part 10: Atypical Designer Drugs (Subscribe)
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