# Essential Oil Provenance of the Remaining Amphetamines

> Essential Oil Provenance of the Remaining Amphetamines traces the botanical ancestry of the PIHKAL (Alexander Shulgin, 1991) compounds the general accounts leave out: DMMDA-2, MMDA-2, MMDA-3a, TMA-5,…

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**Essential Oil Provenance of the Remaining Amphetamines** traces the botanical ancestry of the *PIHKAL* (Alexander Shulgin, 1991) compounds the general accounts leave out: DMMDA-2, MMDA-2, MMDA-3a, TMA-5, TA and IM on the ring side, and MAL, PROPYNYL, IP, PE, MP, MPM, G-5 and FLEA on the side chains grown from those rings. The framework itself — which oil maps to which amphetamine, and why the *in vivo* amination hypothesis turned out to be wrong — is in Shulgin Ten Essential Oils and Shulgin Ten Essential Amphetamines and Metabolic Chemistry, not here. This article separates two things constantly confused: compounds whose **precursor** was an oil, and the larger number whose **ring pattern** was inherited from one while the molecule came out of a flask.

## The epistemic standing of this record

Stated once. Every human observation below is **unblinded self-report**, escalated by hand, with no placebo arm and no blinding — and here several key numbers were not generated by Shulgin at all. DMMDA-2's whole reputation rests on one threshold figure from a taster who was not him, with the synthesis notes lost. He says so in the entry.

## Two kinds of provenance

  DIRECT  : oil ──isomerise──► nitration/oxidation ──reduce──► the amphetamine
            dillapiole ─────────────────────────────────────► DMMDA-2
            apiole     ─────────────────────────────────────► DMMDA

  INHERITED : oil ──► ring pattern ──► synthesised from scratch, oil never touched
            elemicin  ──► 3,4,5-trimethoxy ──► mescaline ──► IP, MAL, PE, MP, PROPYNYL
            asarone   ──► 2,4,5-trimethoxy ──► TMA-2 ────► MEM, MPM
            safrole   ──► 3,4-methylenedioxy ──► MDA ─────► FLEA

Conflating the two produces the common error of imagining a spice cabinet one step from a laboratory shelf.

## Direct provenance: dill, croweacin, and the tetramethoxy oil

### DMMDA-2 (entry 59) — dillapiole, from Oil of Dill

The cleanest direct case in the set, and the most honest confession of thin data in the book — the apiole route run on a different oil:

:"*The procedure used was exactly the same as that described for DMMDA, except that the starting material was dillapiole rather than apiole. The dillapiole was obtained by the careful fractionation of Oil of Dill (as opposed to the isolation of apiole from the careful fractionation of Oil of Parsley). Isomerization to isodillapiole, nitration with tetra-nitromethane... and its reduction with LAH in ether... proceeded in a precisely analogous manner.*"

Dill and parsley are the same chemistry with the oxygens rearranged. The pharmacology is one number from one person:

:"*I was not the taster, and can only quote what I had been given. This same observer found a threshold at 28 milligrams... the activity level was called for in a large review article, and on the basis of the above, both its initials and the value of 5x the potency of mescaline were permanently enshrined in the published literature. What is it really like? I don't know.*"

**Permanently enshrined** on the strength of one threshold: a figure cited for decades traces to a single unrepeated observation by an unnamed person, and the author of the citation says plainly he does not know what the drug does. Yet "*it might be quite a winner if the dosage and the duration were known. It is, after all, one of the ten essential amphetamines.*"

A programme that never happened is recorded too: the TMAs ran six possible isomers, six done; the MMDAs five of six; the DMMDAs stopped at two, because "*the remarkable and totally unexpected activity of DOM*" was "*a much more tempting direction to follow. The remaining four possible DMMDA's have been left to that famous time, a future rainy day.*"

### MMDA-3a (entry 134) — croweacin

MMDA is methoxy (M) + methylenedioxy (MD) + amphetamine (A), with six ring placements numbered to match the TMA convention. Two of them are both "number 3", because the groups can occupy three oxygens in a row in two orientations — hence "*With two possible MMDA-3's it becomes reasonable, in fact essential, to name one of them 'a' and the other 'b'.*" (There is no MMDA-6: a methylenedioxy needs two adjacent oxygens, and TMA-6's 2,4,6 pattern has none.)

Its oil is **croweacin**, 1-allyl-2-methoxy-3,4-methylenedioxybenzene, making MMDA-3a an Essential Amphetamine on the classical reading — with the caveat that "*croweacin is certainly not a practical starting material in synthesis*". Ancestry is not supply.

The human record is three trials at **80 mg** and one at **100 mg**, from clinical work Shulgin calls sketchy, with both quantity and quality compared to **100 micrograms of LSD**. And then:

:"*One subject had a spontaneous peak experience five days after the experiment, and another made a symbolic suicide attempt.*"

The entry's caveat is that these "may or may not be related to the trials". Both halves are the report: the events are recorded, no causal claim is made.

The two-carbon analogue (2C-3a) behaves completely differently: a hint of a psychic energiser at 40 mg, pleasant mood elevation at 65 mg, a brief paresthetic twinge at 80 mg, and at 120 mg "*about the same at one hour, then nothing*". His inference from the flatness: "*such a modest change of effect over a three-fold range of dosage suggests that this compound might have some merit as an anti-depressant*" — "*It would be interesting to know if it blocks serotonin reuptake!*"

### TA (entry 145) — the tetramethoxy oil

2,3,4,5-Tetramethoxyamphetamine qualifies by the same rule: "*Since 1-allyl-2,3,4,5-tetramethoxybenzene is one of ten essential oils, amination would make TA one of the Ten Essential Amphetamines.*" It should work structurally — "*an overlay of TMA (active) and TMA-2 (even more active)*" — but the dose "*might well be in the many tens of milligrams*", and the data behind even that is almost nothing: "*This is pretty thin stuff from which to go out into a world that is populated by pharmacological sharks and stake out claims as to psychedelic potency.*"

## Ring patterns without a named oil: MMDA-2, TMA-5

**MMDA-2** (entry 133), 2-methoxy-4,5-methylenedioxyamphetamine, is "*the second possible methoxy-MDA*" — "*the complete MDA molecule, with the addition of a methoxy group*". What it inherits from MDA is not a precursor but a reputation for splitting opinion: "*Some like it much, and some like it not at all.*" Shulgin adds the worry that the resemblance may be an artefact of knowing the structure: "*It is hard to separate that which is intellectualized from that which is felt.*"

Its neighbours: the two-carbon analogue showed no effects up to 2.6 mg; the four-carbon analogue "*has never even been tasted*"; and the ethoxy "Tweetio" homologue EMDA-2 gave eyes-closed visuals at **135 mg** and, at **185 mg**, "*marvelous eyes-closed visuals (the colors were incredible)*" with body tingles and rushes, lasting about **12 hours** with sleep impossible afterwards — about a third the potency of MMDA-2.

**TMA-5** (entry 161), 2,3,6-trimethoxyamphetamine, is the corpus's worked example of how a shaky number becomes a literature value. It has been "*superficially explored*" by two people, whose reports "*together no more than hint at the possibility that it might be active in the several tens of milligrams*" — yet the published claims are that it is psychedelic at roughly ten times mescaline's potency, in a 30–50 mg range. His verdict on his own published figure is the model for flagging such things: "*Both statements may be true, but confidence in these conclusions must await more extensive trials.*"

## IM, and the ring pattern that was supposed to run backwards

IM (entry 91) is 2,3,4-trimethoxyphenethylamine — mescaline's three oxygens walked one position around the ring. "*Some fifty years ago this material was given the name 'reciprocal mescaline' in that it was believed to exacerbate the clinical symptoms in schizophrenic patients.*" The original claim, as quoted in the entry:

:"*Mescaline, the 3,4,5-trimethoxy-beta-phenethylamine, produces in the normal subject a much stronger over-all intoxication than in the schizophrenic patient, whereas 2,3,4-trimethoxy-beta-phenethylamine has quite the opposite effect. It has little action in healthy individuals, being almost without intoxicating properties, but it is very potent in the schizophrenic.*"

The conclusion drawn at the time was "*an extremely remarkable dependency of the intoxicating action upon the position of the three methoxy groups*". The promised follow-up never appeared. Shulgin does not endorse the claim; he objects to its disposal without replication — "*This is a pretty rich offering, and one that the present medical community has no qualms about discarding*" — notes a modern radiolabelling result in which schizophrenic subjects under methionine loading showed lesser demethylation, and then names what he thinks is in the way: "*But maybe these findings are valid... What must be addressed are the present regulatory restrictions and the Federal law structure. And these are formidable obstacles.*"

## Inherited pattern, built outward: mescaline's 4-oxygen

All of these keep elemicin's 3,4,5-trimethoxy skeleton and vary what hangs off the 4-oxygen. No oil is involved in making them.

{| class="wikitable"
! Code !! 4-substituent !! What the corpus reports
|-
| **MAL** (99) || methallyloxy || "*This testimony can be accurately described as a mixed bag!*"; leads largely to **visual imagery**
|-
| **PROPYNYL** (143) || propargyloxy || "*No experiments have been performed that describe the action of this drug at full level*"
|-
| **IP** (92) || isopropoxy || "*It has proven to be a completely fascinating phenethylamine*"
|-
| **PE** (141) || phenethyloxy || A threshold effect only; "*There is not much there*"
|-
| **MP** (137) || propoxy, on the *meta* oxygen || Inactive; killed the whole meta-position line
|}

**MAL** carries the group's central lesson. A hybrid of AL (an olefin) and CPM (an isostere — same carbon positions, different bonds), it sits among four close relatives that do four different things: CPM leads largely to fantasy, MAL largely to visual imagery, AL is twice as potent as either but shows neither, and PROPYNYL is almost without action at all. Hence:

:"*Although all of them have extremely close structural similarities, there are such great differences in action that one does not dare to generalize.*"

The entry also carries a warning about names, from a bad experience with a differently-named compound: "*The only word that I can use to describe my response to it is to say that I felt I had been poisoned*", and "*From this I warned myself to beware (and to believe in) whatever common name a drug might have been given.*" MAL, he notes with relief, "*did not live up to its name (at least for me)*". One abandoned branch is recorded too: the 2-methoxyethoxy compound gave a yield so bad the project was dropped, while the same grouping with sulfur gave 2C-T-13, potent and interesting.

**IP** unties a recurring confusion: "*In general, the term 'iso' means the other one of two possibilities.*" In isoproscaline the *side chain* rearranges while the ring stays 3,4,5; in isomescaline the *ring pattern* goes from 3,4,5 to 2,3,4 — same prefix, different thing moved, so "*The term 'iso' must always be interpreted in precise context.*" The unmade amphetamine 3C-IP is predicted at "*maybe in the 30 milligram area*".

**PE** states why a threshold report is not a dose estimate — it "*cannot be used to predict with any confidence just what level (if any) would produce psychological effects*" — and closes "*PE may be active at very high levels, and I am not sure just how to get there safely.*" Its benzyloxy homologue Shulgin deliberately names **BZ**, colliding with the military designation for quinuclidin-3-yl benzilate, an incapacitating chemical-warfare agent of which the entry notes 20,000 pounds then in storage. **MP** (metaproscaline) closes its own line: two carbons to three on the *meta* oxygen lost the activity, the isopropyl version MIP was carried as far as the aldehyde and abandoned, and "*There were other fish to fry.*"

## Inherited pattern: asarone's 2,5-dimethoxy shelf, and two outliers

**MPM** (entry 138), the 4-propoxy homologue of TMA-2 and MEM, "*is clearly less active, and this has discouraged me from putting too much more effort in this direction.*" Three homologues went with it: MIPM (never assayed), MBM (no effects up to **12.0 mg**), and MAM (up to **16 mg**: heaviness in chest and head at two hours, no cardiovascular disturbance, no mydriasis — "*This was called an inactive level*").

**G-5** (entry 84) is the extreme of the same ring: a norbornyl bridge across the 3,4-positions of a 2,5-dimethoxyamphetamine, "*about as bulky as has ever been put onto a centrally active molecule*". It is "*as potent as any of the three-carbon Ganesha compounds, but it somehow lacks a little something*" — chiefly "*the generally commented upon absence of visual and related sensory entertainment*". Its hazard note is a negative one, rare enough to record: "*There seems to be no bodily threat to discourage further exploration, but there simply was not the drive to explore it much.*"

**FLEA** (entry 81) sits on safrole's methylenedioxy ring and modifies the nitrogen instead: N-hydroxy-N-methyl-MDA. Dosages and durations are almost identical to MDMA, with a consensus that it is "*not quite as enabling for closeness with others*", moves more towards introspection, and brings slightly increased discoordination in thought — "*Were MDMA unknown, this material would have played its role completely.*" Behind it is the N-hydroxy rule: MDOH is equipotent with MDA, and HOT-2, HOT-7 and HOT-17 are all active analogues of 2C-T-2, 2C-T-7 and 2C-T-17 — which, Shulgin notes, would let almost any marketed amine be reworked outside its patent: "*Remember, Mr. Eli Lilly and Company; you read about it first, right here!*"

## What the provenance is actually worth

1. **The oils fixed the rings, not the molecules.** Calling a compound an "essential amphetamine" is a claim about ring geometry, not about where the material came from.
1. **Oil ancestry predicts nothing about activity.** DMMDA-2, MMDA-3a and TA are all Essential Amphetamines by the rule; one rests on a single borrowed threshold, one produced two adverse events at 80–100 mg, and one has never been given a reliable dose at all. The most interesting compounds here — IP, MAL, FLEA — have no botanical precursor whatsoever.
1. **The metabolic story behind the classification does not hold.** The *in vivo* amination hypothesis is corrected in Shulgin Ten Essential Amphetamines and Metabolic Chemistry; MMDA-3a's entry still carries the original framing, and reads as 1991 reasoning rather than current pharmacology.

## See also

- Shulgin Ten Essential Oils · Shulgin Ten Essential Amphetamines and Metabolic Chemistry — the framework and the metabolic correction
- Allylbenzene Metabolism · Oilahuasca — what the oils actually do in a human liver
- Urine Testing and the Long Search for a Psychiatric Biomarker — the discarded-biomarker pattern behind IM
- Shulgin Structure Activity Relationships Ring Substitution and Potency · Chain Length the Bushy End and the Duration of Action · Cactus Alkaloid Catalogue and the Mescaline Reference Standard
- Shulgins Open Problems Compounds Left at the Aldehyde and Nitrostyrene Stage · Naming the Compounds Codes Greek Names and Shulgin Nomenclature
- Idiosyncratic Responders Inter-Individual Variance and the Street Market — 4-MA, from estragole and anethole
- PIHKAL and TIHKAL · Psychedelic and Psychopharmacology Glossary · Shulgin Rating Scale