# Stack Substances

> Stack Substances is the index of the Van Kush Family Research Institute's substance monographs — every plant, compound and enzyme that appears in the Institute's own stacks, formulations and…

Canonical: https://wiki.soapbox.community/wiki/Stack_Substances
Section: Substances and pharmacology
Last updated: 2026-10-20
Publisher: Library of Ashurbanipal (Van Kush Family Research Institute), https://wiki.soapbox.community

**Stack Substances** is the index of the Van Kush Family Research Institute's substance monographs — every plant, compound and enzyme that appears in the Institute's own stacks, formulations and botanical inventory, written up individually so that each can be checked on its own terms.

Every entry states what is **established**, what is **preclinical**, and what is the **Institute's own hypothesis**, separately. Where a substance has a real hazard, the hazard is on the page rather than in a disclaimer.

## Why the interactions are stated in full

These pages carry preparation detail, dose figures where the literature gives them, and interaction and contraindication warnings in full. That is deliberate and it is the Institute's settled position: **withholding preparation, dose and interaction detail from someone who is going to proceed anyway is the harm this library exists to prevent.** Somebody deciding what to do with a pound of *Mucuna* extract is better served by being told plainly that L-DOPA plus an MAOI is a hypertensive-crisis interaction than by being told to consult a professional about a plant most professionals have never handled.

## The endocannabinoid framework

The organising idea across most of the botanical inventory:

- **Cannabinoid Oilahuasca** — the framework itself: potentiate the body's own cannabinoids by inhibiting the enzymes that clear them, on the model of DMT plus an MAO inhibitor
- **MAGL** — the enzyme that clears 2-AG, ~85% of it
- **FAAH** — the enzyme that clears anandamide
- **Anandamide and 2-AG** — the two endocannabinoids, and why they are not two versions of one thing
- **Endocannabinoid Chemistry and 2-AG Metabolism** — 2-AG biosynthesis via DAGL, spontaneous 1,2-acyl migration to 1-AG, Noladin ether, and virodhamine
- **Cannabinoid Adducts and Conjugates** — chlorinated adducts, macromolecular dimers, Phase II fatty acid conjugation, and cyclodextrin complexes

## Organic chemistry and synthetic pharmacology

Monographs detailing laboratory transformations, reaction kinetics, and pharmacology:

- **Cannabinoid Isomerization** — acid-catalyzed pyran ring closure from CBD into Δ9/Δ8-THC, kinetic vs thermodynamic control, SALLE purification, and why kitchen acids fail
- **Cannabinoid and Tryptamine Prodrugs** — esterification of phenolic hydroxyls, Shulgin's 4-AcO vs 4-OH framework, and the lethal ketene gas pyrolysis hazard of vaporized acetates
- **Stereochemistry in Cannabinoid and Psychedelic Synthesis** — natural (-)-trans enantiomeric purity vs flat carbocation synthetic racemates across cannabinoids, amphetamines, and racetams
- **Airway Irritation and Cannabinoid Prodrug Delivery** — TRPA1/TRPV1 airway triggers, monoterpene mucosal stripping, hydrophilic pre-wash protocol, and water-soluble O-phosphate salts
- **Modified Cannabinoids Matrix** — comparative index and monographs of Δ8, Δ9, HHC (9R vs 9S), THC-O, THCp, THCJD, HU-331, and O-phosphate prodrugs
- **Shulgin Ten Essential Amphetamines and Metabolic Chemistry** — the 10 botanical essential oils and their corresponding amphetamines, refutation of the amination hypothesis, and CYP450 cascades
- **Universal Reaction Templates in Cannabinoid Chemistry** — hydration, hydrogenation, hydrolysis, epoxidation, and addition/removal templates for cannabinoids and terpenes
- **Cannabinoid Photochemistry and Degradation** — UV-C cleavage (CBE), UV-B photo-oxidation (HU-331 pink oil), visible-light photoredox single-electron transfer, and solvent peroxide hazards
- **Antioxidants and Cannabinoid Stability** — free-radical oxidation cascades, rosemary's sacrificial carnosic acid/carnosol protection, metal ion chelation, and membrane fluidization
- **Solvent Chemistry and Polarity in Botanical Extraction** — dielectric constants, partition coefficients (log P), phase separation logic, and why ethanol fails as a nucleophile trap
- **Hemp Industry Scale-Up and Legal Synthesis Protocols** — benchtop thermal runaway, fractional freezing of glacial acetic acid, d-limonene green extraction, SALLE quenching, and the hydrophilic plant pre-wash
- **Cannabinoid Quinones and Novel Derivatives** — oxidation of CBD to HU-331, non-cardiotoxic Topoisomerase IIα catalytic inhibition, neuroprotective aminoquinones (VCE-003.2), and N,O-TMS silylation
- **Structure-Activity Relationships in Psychopharmacology** — Shulgin's TIHKAL #55 (α,N,O-TMS) 2-position rule, cross-receptor migration (serotonin to melatonin to dopamine), and the 5-HT1A oxytocin entactogen bridge
- **69Ron and Oilahuasca Chemistry** — 69Ron's non-toxic d-limonene extraction ("DryTek"), enzyme inhibition sequencing, vendor controversies, and the documented lack of classical psychedelic baseline
- **Allylbenzene Metabolism, Oswald Pathway, and Mace** — E.O. Oswald's in vivo tertiary amine alkaloid pathway via vinyl ketones, and why mace eliminates the heavy trimyristin fat of nutmeg
- **Traditional Spiced Formulations and Synergistic Blends** — the biochemical rationale behind the coffee-almond-cinnamon-vanilla-nutmeg blend, Bedouin spiced coffee, Roman/Medieval Hippocras, and South Asian Paan
- **Isomers, the Analogue Act, and Forensic Chemistry** — chemical isomerism vs CSA statutory definitions, the 1986 Analogue Act, Shulgin's aMT entry, and the five-hole salt shaker metaphor
- **Religious Sacraments, RFRA, and the Temple of True Inner Light** — James Madison's conscience doctrine, the Smith crisis, RFRA strict scrutiny, UDV ayahuasca precedent, and Shulgin's DPT reflection on the Temple of True Inner Light
- **Psychotropics Convention and the UDV Precedent** — the 1971 UN treaty, scheduling tiers, the INCB botanical decoction distinction, and Chief Justice Roberts' unanimous rejection of the DEA's treaty defense in Gonzales v. UDV
- **Shulgin Rating Scale** — Sasha and Ann Shulgin's +/- to ++++ qualitative phenomenological scale for standardizing subjective entheogenic bioassays
- **Colloidal Metals, Electrochemistry, and Nanoparticles** — low-voltage electrolysis, Faraday's laws, constant-current regulation, the coin/copper contamination hazard, and argyria toxicology
- **Rasa Shastra and Ancient Indian Nanochemistry** — Ayurvedic iatrochemistry, multi-cycle Puta calcination, Swarna/Rajata Bhasmas, and modern TEM/XRD characterization of ancient gold/silver nanoparticles
- **Laboratory Equipment and Extraction Engineering** — short-path distillation, rotary evaporators, ultrasonic cavitation, microwave-assisted extraction (MAE), C1D1 cleanrooms, and solvent explosion hazards
- **Cannabinoid and Terpene Electrochemistry** — anodic synthesis of HU-331 quinone, cathodic electro-hydrogenation to HHC, room-temperature Kolbe decarboxylation, and transdermal iontophoresis
- **Cannabinoid Chromatography and Genomics** — HPLC active THC formulas, GC thermal artifacts, Centrifugal Partition Chromatography (CPC), the 5 chemotypes, and marker-assisted breeding
- **Bioelectricity, Forensic Genomics, and Alchemical Transmutation** — gel/capillary electrophoresis, electroporation nanopores, morphogenetic bioelectric fields, STR profiling, headspace GC-MS fire forensics, and Paracelsian spagyric nanochemistry
- **Thiols and Oxygen Congeners in Medicinal Chemistry** — sulfur vs oxygen periodic chemistry, cannabis skunk volatile sulfur compounds (32B1T), glutathione quinone trapping, and Shulgin's 2C-T sulfur series
- **Alkaline Earth Metals, Calcium Signaling, and Strontium Mimicry** — hydroxyapatite crystal lattice substitution, strontium ranelate dual action, Strontium-90 bone seeker beta radiation, and presynaptic calcium channel CB1 inhibition
- **Molar Stoichiometry, Powder Density, and Tolerance Kinetics** — moles vs milligrams, the salt factor equation, bulk density variations, the lethal fallacy of eyeballing powders, and beta-arrestin GPCR tolerance kinetics
- **David E Nichols, Entactogen Pharmacology, and Receptor Mapping** — David E. Nichols' academic legacy, MDMA vs 6-APB benzofuran pharmacology, 5-HT2B cardiac valvulopathy hazards, and the Oilahuasca allylbenzene docking model
- **Colorimetric Reagents and Presumptive Chemical Testing** — Marquis, Mecke, Mandelin, Froehde, Simon's secondary amine enamine reaction, Robadope primary amine, Ehrlich indole bis-indolyl dyes, master reaction matrix, and the fatal adulterant masking trap
- **Ecstasy Pill Forensics and Historical Adulteration Trends** — Texas pre-ban era (Starck Club), the heroin-based pill myth vs GC-MS reality, the 2000s piperazine wave (BZP/TFMPP), synthetic cathinones (mephedrone/methylone), European super-pills, and fentanyl cross-contamination

## Enzyme systems, inhibitors, and biological regulators

Monographs detailing enzymatic kinetics, metabolic cascades, synaptic clearance, and macromolecular inhibitors:

- **The Expanded Endocannabinoid System and FAAH Science** — the endocannabinoidome (eCBome), catalytic Ser-Ser-Lys triad, PEA/OEA signaling, BIA 10-2474 forensics, and C385A genetics
- **Cytochrome P450 System Inhibition and Induction** — CYP3A4/2D6/1A2/2C9/2C19 kinetics, mechanism-based suicide inhibition (grapefruit/piperine), PXR/AhR induction, and prodrug vs active drug divergence
- **Bioavailability: Metabolic Enzymes, Transporters, and Synergistic Delivery** — oral bioavailability equations ($F=f_a \times F_g \times F_h$), Ayahuasca MAOI lesson, grapefruit furanocoumarin suicide inhibition, Racetam/Choline/Alpha-GPC kinetics, Phenylpiracetam lipophilicity, Vitamin C redox shielding, and kitchen synergists (vanillin, cinnamaldehyde, turmeric/piperine 2000% boost, S-acetyl glutathione, ethanol)
- **Sublingual Absorption, Salivary Enzymes, and Mucosal Bioavailability** — non-keratinized sublingual mucosa, internal jugular first-pass avoidance, salivary $\alpha$-amylase and lingual lipase, MUC5B/MUC7 barriers, saponin and terpene permeation drivers, and Henderson-Hasselbalch pH partition shifts
- **Ubulawu, African Oneirogens, and Saponin Pharmacokinetics** — Southern African dream root science (*Silene undulata*, *Helinus integrifolius*, *Synaptolepis kirkii* kirkinine), biosurfactant micro-foams, salivary amylase inhibition, and convergence with Oilahuasca, Ukuphahla, Egyptian Head Cones, and Punic Wax
- **Monoamine Oxidase Inhibitors and Neurotransmitter Systems** — MAO-A vs MAO-B, irreversible vs RIMA (harmalas), dietary tyramine cheese effect, and serotonin syndrome pharmacology
- **Cholinergic Neurotransmission and Cholinesterase Inhibition** — why intact ACh has no reuptake pump, AChE velocity, CHT1 rate-limiting bottleneck, galantamine, huperzine A, and organophosphate aging
- **Enzyme Inhibition Kinetics and Molecular Transporters** — Lineweaver-Burk models (competitive, non-competitive, uncompetitive, suicide), the serine hydrolase superfamily, SLC6 transporters (SERT/DAT/NET), and VMAT2
- **Bacteriophages Endolysins and Biological Inhibitors** — phage biology, holin-endolysin lytic machinery ("enzybiotics"), bacterial CRISPR defenses, Anti-CRISPR (Acr) biological protein inhibitors, and phage-antibiotic synergy
- **Virology, Antivenom Immunology, and Aromatic Antimicrobials** — chlorine radical photolysis, active vs passive immunity, F(ab')2 antivenom fragments, convalescent plasma, and Thieves Oil protease / zinc ionophore enzymology

## Compounds

- **Beta-Caryophyllene** — dietary CB2 agonist; the compound running through nearly every plant below
- **8-Prenylnaringenin** — hops; the most potent natural MAGL inhibitor known, and one of the most potent phytoestrogens known
- **L-Methylfolate** — the only folate that crosses the blood-brain barrier; upstream of all three monoamine systems

## Plants

- **Imphepho** — *Helichrysum* spp.; the ukuphahla incense, and the best vaporiser candidate in the inventory
- **Balm of Gilead, Uziza, and Ancient Resinous Synergies** — *Commiphora gileadensis* and *Piper guineense*; oleo-resins, guineensine/piperine FAAH inhibition, and transdermal penetration
- **Apotropaic Magic, Bes Mugs, Syrian Rue, and Egyptian Wax Alchemy** — Bes vases, *Peganum harmala* harmine/harmaline fumigation, Bastet unguent jars, and beeswax-imphepho soap
- **Yin Chen Hao** — *Artemisia capillaris*; sold as a psychoactive, actually a liver medicine
- **Mucuna Pruriens** — velvet bean; 3–7% L-DOPA, and the highest-risk material held
- **Kava** and **Kava Potentiation** — *Piper methysticum*; yangonin binds CB1 and inhibits FAAH; the 5-category potentiation framework, black pepper synergy, and the liver collision
- **Black Pepper** — *Piper nigrum*; four distinct activities from one kitchen spice
- **Maca** — *Lepidium meyenii*; macamides as structural analogues of anandamide
- **White Sage** — *Salvia apiana*; and why the sourcing question is the whole entry
- **Cannabis** and **Cannabis Harm Reduction**

## Nutrients and cofactors

- **Creatine** — the best-evidenced supplement in common use, and the reason it raises serum creatinine without harming the kidney
- **Vitamin K2** — the vitamin that decides whether calcium goes into bone or into arteries; MK-4 vs MK-7 is a half-life question
- **Chelated Minerals** — form governs uptake; and elemental content is where the labels mislead
- **Liposomal Vitamin C** — the SVCT1 absorption ceiling, what encapsulation actually buys, and why splitting the dose beats most of it
- **Silicon and Collagen** — orthosilicic acid, not quartz
- **B-Vitamins** — picamilon, "read your urine", and the B6 neuropathy nobody mentions

## Nootropics

- **The Amplification Framework** — substrate, cofactor amplifier, degradation inhibitor; the model the rest of this section is arranged by
- **Racetams** — piracetam and family; strong in clinical populations, weak in the healthy adults who buy it
- **Choline Donors** — alpha-GPC, citicoline and the rest; not interchangeable, and the TMAO question
- **Galantamine** — the one lucid-dream aid with a randomised trial behind it, and a real cardiac-conduction drug

## Recorded only as a warning

- **Datura** — the single entry in this library where no dose is given, because no accurate dose exists to give; benztropine 1 mg clinical parallels, Sadhu smoke pyrolysis, and Shulgin tasting titration
- **Old World vs. New World Visionary Botanicals: Toxicity, Titration, and the Shulgin Method** — Old World poison plants (henbane, wolfsbane, belladonna, foxglove) vs New World visionary flora (psilocybin, peyote, ayahuasca); Sadhu snake venom smoking on charas; and Shulgin museum-level titration

## Preparation

Vaporisation temperature governs which fraction of a plant is actually delivered, and the bands are narrow enough that temperature control is a formulation decision rather than a comfort setting:

{| class="wikitable"
! Fraction !! Temperature !! Found in
|-
| Monoterpenes (α-pinene, 1,8-cineole) || 155–175 °C || Imphepho, *Artemisia*
|-
| Sesquiterpenes (β-caryophyllene) || 175–200 °C || Imphepho — the CB2-active fraction
|-
| Scoparone || ~200 °C || *Artemisia capillaris*
|-
| Flavonoids || 200–230 °C || most herbs
|-
| **L-DOPA — degrades** || **>200 °C** || Mucuna — not a vaporiser candidate
|}

## The interactions worth knowing before anything else

- **L-DOPA + MAOI** — hypertensive crisis. Mucuna with any harmala-containing preparation, syrian rue, or a prescribed MAOI.
- **MAOIs/RIMAs + Serotonergic agents (SSRIs, SNRIs, MDMA, DXM, Tramadol)** — fatal serotonin toxicity. Requires strict 2-to-5 week drug washout intervals; see Monoamine Oxidase Inhibitors and Neurotransmitter Systems.
- **Irreversible MAOIs + Aged food tyramine ("Cheese Effect")** — severe hypertensive crisis and stroke from displaced peripheral norepinephrine; see Monoamine Oxidase Inhibitors and Neurotransmitter Systems.
- **Piperine / Grapefruit + Prescription medications** — mechanism-based and competitive inhibition of CYP3A4, CYP2D6 and P-glycoprotein causes toxic blood accumulation of narrow-therapeutic-index drugs; see Cytochrome P450 System Inhibition and Induction.
- **Cholinesterase inhibitors (Galantamine, Huperzine A) in cardiac conduction disease** — stimulates cardiac M2 receptors, risking severe bradycardia, AV block, and syncope; see Cholinergic Neurotransmission and Cholinesterase Inhibition.
- **Kava + alcohol, sedatives, or anything hepatic** — see Kava.
- **8-PN in hormone-sensitive conditions** — see 8-Prenylnaringenin.
- **Folate without checking B12** — see L-Methylfolate.
- **B6 above ~100 mg/day** — irreversible sensory neuropathy; see B-Vitamins.
- **Vitamin K2 with warfarin** — direct antagonism of the drug's mechanism; see Vitamin K2.
- **Galantamine with bradycardia, asthma or an anticholinergic** — see Galantamine.
- **Chronic complete MAGL inhibition** causes CB1 desensitisation. More is not better; see MAGL.
- **Vaporizing acetate prodrugs (THC-O-acetate, Vitamin E acetate)** — coil temperatures >200 °C pyrolyze esters into toxic ketene gas (CH2=C=O), causing severe acute chemical pneumonitis and pulmonary edema; see Cannabinoid and Tryptamine Prodrugs and Airway Irritation and Cannabinoid Prodrug Delivery.
- **Unwashed acid-isomerized extracts** — inhaling residual mineral acids (HCl, H2SO4, pTSA) or chlorinated adducts causes acute airway destruction; see Cannabinoid Isomerization and Cannabinoid Adducts and Conjugates.
- **Space Paste or heavy nutmeg abuse** — toxic anticholinergic-like delirium and possible DNA-reactive 1'-hydroxy sulfate metabolites; see Shulgin Ten Essential Amphetamines and Metabolic Chemistry.
- **Open-blasting volatile hydrocarbon solvents (butane/propane)** — catastrophic fuel-air thermobaric explosions; butane pools along floors (vapor density 2.08 g/L) and ignites at just 1.8% LEL from refrigerator relays, static electricity, or pilot lights; see Laboratory Equipment and Extraction Engineering.

## Related

Library of Ashurbanipal · Ubulawu, African Oneirogens, and Saponin Pharmacokinetics · Sublingual Absorption, Salivary Enzymes, and Mucosal Bioavailability · Bioavailability: Metabolic Enzymes, Transporters, and Synergistic Delivery · Balm of Gilead, Uziza, and Ancient Resinous Synergies · Old World vs. New World Visionary Botanicals: Toxicity, Titration, and the Shulgin Method · Apotropaic Magic, Bes Mugs, Syrian Rue, and Egyptian Wax Alchemy · PIHKAL and TIHKAL · Psychedelic and Psychopharmacology Glossary · Modified Cannabinoids Matrix · The Expanded Endocannabinoid System and FAAH Science · Cytochrome P450 System Inhibition and Induction · Monoamine Oxidase Inhibitors and Neurotransmitter Systems · Cholinergic Neurotransmission and Cholinesterase Inhibition · Enzyme Inhibition Kinetics and Molecular Transporters · Bacteriophages Endolysins and Biological Inhibitors · Virology, Antivenom Immunology, and Aromatic Antimicrobials · Laboratory Equipment and Extraction Engineering · Cannabinoid and Terpene Electrochemistry · Cannabinoid Chromatography and Genomics · Bioelectricity, Forensic Genomics, and Alchemical Transmutation · Thiols and Oxygen Congeners in Medicinal Chemistry · Alkaline Earth Metals, Calcium Signaling, and Strontium Mimicry · Molar Stoichiometry, Powder Density, and Tolerance Kinetics · David E Nichols, Entactogen Pharmacology, and Receptor Mapping · Colorimetric Reagents and Presumptive Chemical Testing · Ecstasy Pill Forensics and Historical Adulteration Trends · Food Pyramid and Supplements · Kyphi · Ukuphahla · Head Cone · Punic Wax