Designer Drug Exposé: Psychedelic Phenethylamines
Designer Drug Exposé: Psychedelic Phenethylamines
Mescaline is the king of the psychedelic phenethylamines — but it's just the tip of the iceberg. Psychedelic families covered includes 2CX, DOX, NBX, & other mescaline-analogs.
The phenethylamine family is so big we’ve had to break it down into two parts — the psychedelic phenethylamines, which we’ll explore below, and the amphetamines — a massive subgroup of phenethylamines we’ll be exploring in part 5 of this series.
Hands down, the most famous member of the phenethylamine group is mescaline, the active ingredient in two species of cactus — peyote (Lophophora williamsii) and San Pedro (Echinopsis pachanoi).
Over several decades, chemists have played with the base structure of mescaline, adding and removing functional groups to create thousands of brand new designer psychedelics, stimulants, and even a few empathogens.
Most of the designer phenethylamines available today come from the work of the late psychedelic chemist Alexander Shulgin. Throughout the 70s and 80s, Shulgin systematically altered the chemical structure of mescaline. Over several decades he created over 230 new psychedelic substances — nearly 200 of which are classified as phenethylamines.
Today, many of his creations remain obscure research chemicals sought out only by fervent psychonauts. Exceptions include most of the 2C-X group (2C-B, 2C-T-2, 2C-T-7, 2C-E), some NBOMes, as well as DOX compounds like DOB and DOM — all of these drugs are now universally prohibited.
Some designer phenethylamines that stand out include:
Benzofurinated 2CX Drugs — such as 2C-B-FLY, 2C-B-DRAGONFLY, and 2C-B-BUTTERFLY.
Proscaline — a close analog of mescaline with similar effects. Also, the closely related isoproscaline.
DOC & Other Unexplored DOX Compounds — a very strong, very long-lasting group of psychedelics.
The Phenethylamines: Part Stimulant, Part Psychedelic
Phenethylamines are a bit of a mixed bag when it comes to their effect profiles. Many produce psychedelic visuals similar to LSD (lysergic acid diethylamide) and magic mushrooms; some have a more substantial effect on the body, and some are exclusively considered stimulants, with minimal psychedelic qualities.
All phenethylamines, by definition, feature a dopamine molecule — which is embedded in their base chemical structure.
The integration of a dopamine molecule allows many of these compounds to bind with dopamine receptors in the brain (D1 and D2 subtypes).
Some of these compounds are also able to bind to the serotonin receptors (5HT2A, 5HT2B, and 5HT2C subtypes).
The specific effects of an individual compound depends on which receptors it binds with.
Psychedelic phenethylamines such as mescaline, proscaline, 2C-X drugs, DOX, and NBOMes, generally have a higher affinity for serotonin receptors — which is what allows them to produce similar psychedelic qualities to tryptamines like LSD, psilocybin, and DMT which work through the same receptors.
Other phenethylamines, such as the amphetamine subgroup as well as some DOX compounds, have a higher affinity for the dopamine receptors — giving them powerful stimulant effects and only mild psychedelic qualities.
Most phenethylamines fall somewhere in the middle, producing a blend of stimulant (dopaminergic) and psychedelic (serotonergic) qualities. This is why phenethylamine psychedelics tend to be more energizing than their tryptamine counterparts.
Very few (if any) phenethylamines are considered “relaxing” or “couch-locking” in the way that magic mushrooms, 5-MeO-DMT, or 4-HO-MET can be. They all have some stimulant effects that give people the desire to get up and move around throughout the trip. They also tend to produce more “body load” than tryptamines — which refers to uncomfortable physical effects, like griping, muscle cramping, or general discomfort.
Mescaline Analogs
Most of the compounds we’ll explore below can be categorized as “mescaline-analogs.” Mescaline has been used as a starting point for hundreds of designer drug molecules, including the entire 2C-X family and several DOX compounds, which we’ll explore in more detail later.
There are several mescaline analogs that classify as designer drugs that don’t quite fit into the other categories. This includes:
Proscaline (3,5-dimethoxy-4-propyloxyphenethylamine) — A very close, unregulated alternative to mescaline.
Methallylescaline (3,5-dimethoxy-4-methallyloxyphenethylamine) — Invented by Alexander Shulgin. The effects of this compound are inconsistent but long-lasting (12–14 hours).
Allylescaline (3,5-dimethoxy-4-allyloxyphenethylamine) — Invented by Otakar Leminger in the 70s. Produces a “warm” entactogenic effect similar to MDMA (albeit much milder).
Escaline (3,5-dimethoxy-4-ethoxyphenethylamine) — The phenethylamine analog of 3C-E.
Isoproscaline (4-isopropoxy-3,5-dimethoxyphenethylamine) — Invented by David E. Nichols and his team at Purdue. Closely related to proscaline.
3-TME (3,4,5-trimethoxyamphetamine) — An amphetamine analog of mescaline
There are also several analogs that were thought to produce psychedelic effects similar to mescaline but have proven themselves impotent. An example of this is a compound called buscaline (4-butoxy-3,5-dimethoxyphenethylamine), which was invented by Alexander Shulgin in the 1970s. Buscaline has no psychoactive effects — only adverse physical side effects like rapid heart rate, anxiety, and diarrhea. Other examples like this include 4-TME and 5-TME.
Surprisingly, most of these mescaline analogs are not on the DEA or UN-restricted substances lists. Only Sweden has taken independent steps to ban specific mescaline analogs. Currently, only escaline is explicitly included under the Schedule I standing in the US.
Proscaline, allylescaline, isoproscaline, and 3-TME aren't technically included and, therefore, qualify as designer drugs. All four may be considered illegal under the Federal Analogue Act due to their structural similarities to mescaline, but this law has not been well enforced in recent decades.
2C-X Compounds
The 2C-X family contains the majority of the psychedelic phenethylamines (the amphetamine group is more extensive, but most aren't considered psychedelic).
There are 70 known compounds in this family, but the possibilities for new functional groups, and therefore new members, is nearly endless.
The 2C-X group challenges the conventional definition of "designer drug" because most have been on the Schedule I drug list in the US since 1995. 2C-B, 2C-C, 2C-D, 2C-E, 2C-N, 2C-H, 2C-I, 2C-T-2, and 2C-P are all explicitly mentioned as Schedule I drugs.
A few examples of members that aren't on the list include all the substituted benzofuran versions, including 2C-B-BUTTERFLY, 2C-B-DRAGONFLY, 2C-B-FLY, and 2C-C-FLY, 2C-D-FLY, as well as 2C-F, 2C-G, 2C-iP, 2C-O, 2C-V, HOT-7, BOD, BOB, βk-2C-B, and others.
The effects of most 2C-X psychedelics can be described as a combination of MDMA and LSD (lysergic acid diethylamide). They exhibit varying intensities of psychedelic, empathogenic, and stimulant qualities.
The 2C-X family is highly dose-dependent — meaning the effects of lower doses produce dramatically different effects than high doses (in most cases).
Lower doses of 2C-X compounds tend to feel more stimulating and euphoric, while higher doses are much more psychedelic. Many of these compounds produce a strong "body load" in higher doses.
There are many members of this group, each with key differences in qualitative effects and potency. Some drugs, like 2C-I, are incredibly potent — active in doses as low as 2 mg. Others, such as 2C-T-3, are virtually inactive. The most popular member of this group — 2C-B — is active in doses starting around 5 mg (oral).
NBX Compounds (N-Benzylphenethylamines)
The NBX compounds are a subclass of phenethylamines with a unique benzyl group attached to the nitrogen molecule. There are several different subgroups of the NBX class.
NBX functional groups are usually added to the base structure of 2C-X drugs (such as 2C-B, 2C-D, or 2C-I ), but they can also be combined with mescaline (ex: mescaline-NBOMe), DOX (ex: DOB-NBOMe), and various others.
Examples of NBX subgroups include:
25X-NBOMe
25X-NBOH
25X-NBBr
25X-NBMD
25X-NBF
25-X-NBMeOH
Some examples of NBX compounds that aren't listed on the DEA or UN's restricted substances list include 2CBCB-NBOMe, 25B-NB23DM, 25B-NB25DM, 25B-NBF, 25B-NBOH, 25C-NBF, 25C-NBOH, 25D-NBOMe, 25E-NBOMe, 25I-NBF, 25I-NBMD, 25I-NBOH, 25iP-NBOMe, 25H-NBOMe, 25N-NBOMe, 25P-NBOMe, and Mescaline-NBOMe.
NBOMes
By far, the most popular members of the NBX class are the NBOMes, which were initially created by Dr. Shulgin. In this group, 25I-NBOMe, 25C-NBOMe, and 25B-NBOMe are all explicitly banned in the US, Canada, Australia, and Europe.
Most of the other members of this class remain unscheduled but are unpopular within the designer drug community due to their negative and often dangerous side effects.
The addition of an NBOMe group to other psychedelics dramatically increases its potency.
Here are a few examples comparing the standard psychoactive dose of NBOMes with their 2C-X analogs:
25I-NBOMe (0.5–0.7 mg) | 2C-I (10–20 mg) | NBOMe is 20–40X Stronger
25B-NBOMe (0.3–0.5 mg) | 2C-B (15–25 mg) | NBOMe is 30–80X Stronger
25C-NBOMe (0.3–0.7 mg) | 2C-C (30–50 mg) | NBOMe is 40–166X Stronger
These 3 NBOMes feature similar potency to LSD. They're one of the few psychedelic classes active in submilligram doses. Most psychedelics, including the entire 2C-X group, as well as mescaline, DMT, and psilocybin analogs, all require several miligrams to achieve an active dose. Some, like mescaline or MDMA, require over 100 mg.
Because of the similarities in effects and potency and the high cost of manufacturing LSD (all precursor ingredients are highly controlled), NBOMes are a common ingredient used to make fake acid.
The problem is that, while the effects are similar, NBOMes are NOT a safe alternative to LSD.
NBOMes take a physical toll on the body, and most of them are considered toxic. This, combined with a slow onset (1–2 hours), makes them especially dangerous. Thinking it's acid, users often take one tab, wait an hour, then and after nothing happens, they double down on a second one. Once both tabs take effect, it can very quickly lead to overdose.
NBOMe overdose has led to many deaths over the years and put countless more in the hospital.
NBOMes are the number one reason why you should always test a sample of your LSD before you take it.
Some people enjoy using NBOMes, but if users want to take these compounds, they need to be especially careful when it comes to dosing. This may not be the case with acid where it’s common (and general considered safe) to consume more than one tab at a time.
Fortunately, there's another way to detect if your tab contains NBOMes (though this method is not nearly as effective as a reagent test). NBOMes have an acrid bitter taste, while LSD is flavorless. If you detect bitterness in your acid, spit it out immediately.
NBOH
The 25X-NBOH group shares many similarities with NBOMes but tend to have a shorter duration of effects and are generally milder. They're also exceptionally potent (active in doses below 1 mg) and toxic. The difference between a psychoactive dose and a fatal overdose is minuscule.
Some people suggest the NBOH compounds have less body load than NBOMes, but this likely comes from their lower potency rather than any particular difference in effects. Equivalent doses of NBOH feel nearly identical to NBOMes — this is the case for both the good parts and the bad parts.
Overall, the NBOH class has never achieved widespread popularity. They've been around since at least 2012 but remain in use only by the most fervent psychonauts. This likely stems from their negative health risks and lack of any distinctive advantages over conventional psychedelics. You’re much better off just taking LSD or other lysergamides instead.
There is no explicit mention of NBOH compounds on either the DEA restricted substances list or the UN Convention on Psychotropic Substances.
Some examples of NBOH drugs include 25B-NBOH (2C-B analog), 25C-NBOH (2C-C analog), 25I-NBOH (2C-I analog), 25D-NBOH (2C-D analog), and 25E-NBOH (2C-E analog).
DOX Compounds
The DOX family sits at the intersection where psychedelics and stimulants meet. They're a subgroup of amphetamines, but due to their psychedelic qualities, I've decided to cover them here, too.
The effects of this group are somewhat similar to the 2CX family — featuring unique cartoon-like vibrancy, a dramatic boost in energy, and deep psychedelic introspection. They're also very stimulating, which makes them a popular party drug at raves.
Early members of the DOX family were first synthesized and tested by Alexander Shulgin in the 1970s. Shulgin published his findings, along with the first recorded trip reports for these substances, in his first book (co-authored by his wife, Ann), PiHKAL. One of these drugs, DOM — also known as “STP” (“Serenity, Tranquility, and Peace”) — even made it into the couple’s “magical half-dozen” — which was a shortlist of their favorite psychedelics of all time.
DOM is active at doses as low as 1 mg and lasts between 18 and 36 hours. This compound was initially sold as a designer drug alternative to LSD after it was prohibited in 1965. DOM itself was banned about a decade later.
DOX drugs take a notoriously long time to kick in. While most drugs take about 30-60 minutes, it’s common for users taking DOX drugs to have to wait 3-6 hours before feeling any of the effects.
On the flip side, these compounds last significantly longer than usual — with most remaining in full force 24 hours later.
DOX compounds are also shockingly potent. Drugs like DOB and DOI produce profound psychedelic effects in doses under 1 mg. The only other classes of drugs potent enough to be active doses this low are lysergamides, benzodiazepines, and NBOMes.
Only a few DOX compounds are explicitly listed on the DEA’s restricted substances list. This includes DOM, DOB (the DOX version of 2C-B), DOET, Aleph-2 (and other Aleph analogs), and TMA analogs.
Unregulated examples include DOAM, DOB-5-hemifly, DOB-FLY, DOBU, DOBZ, DOC, DOCN, DODC, DODFM, DOEF, DOF, DOI, DOI-2-hemifly, DOiP, DOiPR, DOMOE, DOMOM, DON, DOPF, DOPR, DOTFE, DOTFM, DOTHFM, DOYN, and numerous others.
Structurally, DOX compounds are most similar to 2CX drugs. They look nearly identical, except for an additional alpha-methyl group. This extra group shares some resemblance with amphetamines and presumably allows them to interact more strongly with dopamine (which produces more stimulant and entactogenic qualities).
Designer Drug Series
This has been part 3 in an 8-part series on designer drugs. Read some of our past series using the link below, or subscribe to receive new posts as they’re released in upcoming weeks:
Part 3: Psychedelic Phenethylamines
Part 8: Sedative Hypnotics & Opioids (Subscribe)
Part 9: Deliriants (Subscribe)
Part 10: Atypical Designer Drugs (Subscribe)
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