Allylescaline

# Research Output: Allylescaline

**Substance:** Allylescaline (AL)  
**PSX ID:** PSX-0095  
**Research date:** 2026-05-10  
**Provenance ID:** 31867516-095a-4c7a-a1f9-44e83641e1c2  

---

## Chemical Identity

**Verified against PubChem CID 44719469 [Ref 3] and IsomerDesign PiHKAL database [Ref 21]:**

| Property | Value | Source |
|---|---|---|
| Molecular formula | C₁₃H₁₉NO₃ | PubChem CID 44719469 [Ref 3] |
| Molecular weight | 237.29 g/mol | PubChem [Ref 3]; IsomerDesign [Ref 21] |
| IUPAC name | 2-(3,5-dimethoxy-4-prop-2-enoxyphenyl)ethanamine | PubChem [Ref 3] |
| Canonical SMILES | NCCc1cc(OC)c(c(c1)OC)OCC=C | IsomerDesign [Ref 21] |
| InChIKey | JNUAYHHGCXYBHX-UHFFFAOYSA-N | PubChem [Ref 3]; IsomerDesign [Ref 21] |
| PubChem CID | 44719469 | PubChem [Ref 3] |
| CAS (free base) | 39201-75-7 | Cayman Chemical [Ref 20] |
| CAS (HCl salt) | 39201-76-8 | Cayman Chemical [Ref 20] |
| HCl MW | 273.8 g/mol | Web sources |

**Common synonyms:** AL (Shulgin code), allylmescaline, 4-allyloxy-3,5-dimethoxyphenethylamine, 3,5-dimethoxy-4-allyloxyphenethylamine

**Brief data verification:** All chemical identity fields in the seed brief (formula C₁₃H₁₉NO₃, MW 237.29, IUPAC name, PubChem CID blank) are confirmed correct by PubChem [Ref 3]. The brief was missing PubChem CID (44719469), SMILES, and InChIKey — all now confirmed.

**Physical form:** Hydrochloride salt is a crystalline solid; purity typically >95% in research-grade samples (Cayman Chemical [Ref 20]). Approximate solubility of HCl salt in ethanol ~10 mg/mL; ~3 mg/mL in DMSO (web sources; not peer-reviewed). No melting point data found in peer-reviewed literature.

**Structural description:** Allylescaline is a member of the "scaline" subgroup of phenethylamines — mescaline analogues retaining the 3,5-dimethoxy substitution pattern but replacing mescaline's 4-methoxy group with an ether-linked substituent. In allylescaline, that substituent is a prop-2-en-1-yl (allyloxy) group, making it the allyl homolog of escaline (4-ethyloxy) and proscaline (4-propyloxy).

---

## Pharmacology

### Mechanism of Action

No published binding affinity data (Ki or EC50 values) exists for allylescaline at any receptor. All receptor pharmacology below is inferred from structural class.

**By structural class inference:**
Allylescaline belongs to the phenethylamine psychedelic class, which acts primarily as agonists at serotonin 5-HT₂A receptors expressed on neocortical pyramidal cells (Nichols 2004 [Ref 16]). Activation of 5-HT₂A receptors leads to increased cortical glutamate levels, presumably via presynaptic receptor-mediated release from thalamic afferents [Ref 16]. The compound is also inferred to act at 5-HT₂C receptors, consistent with mescaline class pharmacology.

The parent compound mescaline is a full agonist at 5-HT₂A receptors — the 3,5-methoxy groups of the ring must remain conformationally mobile for receptor activation, as conformational restriction of these groups abolishes activity (Monte et al. 1997 [Ref 5]). Allylescaline's 4-allyloxy modification of the central (para) position, rather than the flanking 3,5 positions, is predicted to be pharmacologically tolerated based on the SAR of mescaline analogs (McLean et al. 2006 [Ref 6]).

**Potency comparison (user-report data only):**
Allylescaline is reported to be approximately 10-fold more potent than mescaline (Wikipedia [Ref 15], corroborated by Leminger's self-reports [Ref 1] and PiHKAL dose range [Ref 2]). Among Leminger's scaline series, the potency ranking was allylescaline > proscaline > escaline [Ref 1]. The allyloxy substituent's greater lipophilicity relative to the ethyloxy (escaline) and propyloxy (proscaline) groups may contribute to enhanced CNS penetration or receptor affinity, but this is not confirmed by published binding studies.

**FLAG for human review:** No published in vitro binding data (Ki, EC50) exist for allylescaline at 5-HT₂A, 5-HT₂C, or any other receptor. All receptor pharmacology statements rely on structural analogy. This represents a significant gap.

### Pharmacokinetics

No published pharmacokinetic data exists for allylescaline. The following is inferred from the closest studied analog (mescaline) and from class data on structurally related dimethoxyphenethylamines:

**By mescaline analog inference (Mueller et al. 2025 [Ref 7]):**
- Route of administration: oral (sole reported ROA for allylescaline)
- Mescaline is absorbed from the GI tract following oral administration
- The 2025 human PK/PD study of oral mescaline HCl provides the first controlled pharmacokinetic dataset for the scaline class parent compound [Ref 7]

**Metabolism (class inference):**
Dimethoxyphenethylamines are primarily metabolized via monoamine oxidase (MAO)-mediated deamination and cytochrome P450-mediated O-demethylation. For structurally related dimethoxyphenethylamines (NBOMe series), CYP3A4 and CYP2D6 have been identified as the major metabolic enzymes (Nielsen et al. 2017 [Ref 12]). For allylescaline specifically, the allyloxy group at position 4 introduces a metabolic vulnerability at the double bond (epoxidation, allylic oxidation) that is absent in escaline and proscaline, but no published metabolic studies exist for allylescaline.

**FLAG for human review:** All PK data for allylescaline is class-level inference. No published Tmax, Cmax, half-life, bioavailability, or urinary recovery data exists for allylescaline.

---

## History

### Discovery and First Description

Allylescaline was first synthesized and self-experimented upon by **Otakar Leminger**, a Czechoslovakian industrial chemist based near Ústí nad Labem on the Elbe River north of Prague (CountYourCulture/Chapman 2012 [Ref 14]). Upon retirement in the early 1970s, Leminger published his synthesis and self-experimentation results:

> Leminger O. "A Contribution to the Chemistry of Alkoxylated Phenethylamines." *Chemický průmysl* (Chemical Industry), vol. 22, p. 553, 1972. [Ref 1]

This 1972 paper describes the synthesis of five novel phenethylamines — allylescaline, proscaline, escaline, MAPEA (3-methoxy-4-allyloxy-phenethylamine), and MEPEA (3-methoxy-4-ethoxy-phenethylamine) — and reports self-experimentation across all of them [Ref 1].

Leminger reported that at 20 mg, allylescaline produced: vertigo, pleasant excitation, warm color perception, plastic-appearing objects, colorful hallucinations in a dark room, "breathing" of surfaces, and restless sleep lasting more than 12 hours [Ref 1, Ref 14]. He described allylescaline as "the most active compound that he had studied" [Ref 2].

### Alexander Shulgin and PiHKAL

Leminger's paper was brought to Alexander Shulgin's attention approximately ten years after its publication by a researcher named Stanislov Wistupkin (CountYourCulture/Chapman 2012 [Ref 14]). Shulgin subsequently included allylescaline in his 1991 book *PiHKAL: Phenethylamines I Have Known and Loved*, as **entry #2, code AL** (Shulgin & Shulgin 1991 [Ref 2]).

In PiHKAL, Shulgin documented:
- Dosage: 20–35 mg
- Duration: 8–12 hours
- Three qualitative self-reports:
  - At 24 mg: onset within 10 minutes; "clear-headedness and an abundance of energy"; creative, free-flowing states; smooth comedown
  - At 24 mg: onset at 50 minutes, peak at 75 minutes; "wholly social in nature" with fluid speech; no visual or sensory enhancement; sleep required medication; lingering effects the following day
  - At 35 mg: "+1" effects at 35 minutes, "+2" by one hour; dissociated feel; persistent hangover; head congestion unaffected
- Commentary: attribution to Leminger; note that the corresponding amphetamine homolog (3C-AL) was "both unsynthesized and unexplored" as of 1991

PiHKAL remains the only English-language primary published source documenting human self-experimentation with allylescaline.

### Research Chemical Market

Allylescaline was encountered as a novel designer drug on the European research chemical market in 2013, and was notified to the EMCDDA during that period [Ref 15]. NMR spectroscopic characterization of grey-market allylescaline samples from North American and European vendors was conducted by Chapman & Avanes in 2015 (PeakAL report [Ref 4]).

---

## Subjective Effects

Published descriptions of allylescaline's effects derive exclusively from two primary sources: Leminger's 1972 Czech paper [Ref 1] and Shulgin's 1991 PiHKAL [Ref 2]. No controlled human studies exist. The effect profile below is reconstructed from these self-reports.

### Effects documented in primary literature

**From Leminger 1972 at 20 mg [Ref 1]:**
- Vertigo
- Pleasant excitation
- Warm color perception
- Objects appearing plastic or malleable
- Colorful hallucinations in darkness
- Visual breathing effects
- Restless sleep lasting >12 hours

**From PiHKAL 1991 [Ref 2] (three reports, 24–35 mg):**
- Onset ranging from 10 to 50 minutes across reports
- Peak at approximately 75 minutes (24 mg report)
- Energized, "clear-headed" quality at lower doses
- Primarily social/communicative effects; at least one report noted absence of visual/sensory enhancement at 24 mg
- "+2" effects (Shulgin scale) at 35 mg, characterized as somewhat dissociative in quality
- Hangover sensation noted at 35 mg
- Sleep difficulty; sleep required medication in one report
- Effects persisting into the following day

**Duration:** Consistently described as 8–12 hours in Shulgin's documentation [Ref 2]; Leminger's 20 mg self-experiment lasted >12 hours [Ref 1].

**FLAG for human review:** The dose/duration seed data in the brief (threshold 15 mg, light 20–30 mg, common 30–40 mg, strong 40–60 mg, heavy 60+ mg) is not directly sourced from Shulgin's PiHKAL (which gives only 20–35 mg range). The extended dose range (especially 40–60 mg "strong" and 60+ mg "heavy") has no published primary source — Shulgin explicitly noted doses above 35 mg "remain unexplored" [Ref 2]. Dose ranges above 35 mg rely entirely on community extrapolation, not published data.

**Onset discrepancy:** The brief states onset of 45–240 minutes. PiHKAL reports onset ranging from 10–50 minutes across three user reports [Ref 2]. The 45–240 minute range in the brief is substantially broader and slower than PiHKAL-documented onset. This warrants editorial review — it may reflect community-gathered data extending Shulgin's small sample, but the upper bound of 240 minutes is not sourced to any published record.

### Effect taxonomy mapping (seed data assessment)

The 37 seed effect slugs are all tagged as "community_consensus_large/medium" provenance with null intensity/frequency values. No controlled studies exist to confirm, refute, or quantify any of these effects for allylescaline specifically. The effects listed are plausible for a mescaline-class 5-HT₂A agonist psychedelic and broadly consistent with the published self-reports in PiHKAL and Leminger. Notable points:

- **Visual effects** (geometry, drifting, color-enhancement, internal-hallucinations, etc.): consistent with psychedelic phenethylamine class and with Leminger's description of "colorful hallucinations" [Ref 1]; however, one PiHKAL report at 24 mg noted *no* visual enhancement — suggesting visual effects may be dose-dependent and present primarily at higher doses
- **Stimulation, cognitive-euphoria, spontaneous-body-sensations**: consistent with Shulgin reports at 24–35 mg [Ref 2]
- **Empathy-enhancement, emotional-enhancement**: plausible for mescaline-class; not explicitly documented in published allylescaline reports
- **Entity-contact, unity-and-interconnectedness**: possible at higher doses but no published documentation for allylescaline
- **Sexual-arousal-enhancement**: no published documentation
- **Delusions**: no published documentation; potentially an artifact of very high dose extrapolation

---

## Safety & Toxicity

### Published toxicity data

No LD50 data, no toxic dose data, and no overdose case reports exist for allylescaline in published literature. Cayman Chemical's product page explicitly states: "the physiological and toxicological properties of this compound are not known" [Ref 20].

The brief correctly notes: "toxic dose is unknown."

### Class-level safety data (mescaline analog inference)

The most relevant class-level adverse event data comes from a systematic review of mescaline (Shaw et al. 2026 [Ref 19]), which identified hypertension, headache, nausea, and vomiting as the most commonly reported adverse effects across 66 studies. These AEs are expected to be relevant to allylescaline given its structural similarity to mescaline.

The 2C-series phenethylamine toxicology review (Dean et al. 2013 [Ref 8]) identified the following AEs in the broader ring-substituted phenethylamine class: hallucinations, agitation, aggression, dysphoria, hypertension, tachycardia, seizures, hyperthermia, and excited delirium in fatal cases. Five deaths have been reported in the literature attributed to 2C-series drugs — however, these involve the 2,5-dimethoxy substituted 2C series, not the 3,5-dimethoxy scaline series, and are not directly comparable to allylescaline.

The designer drug review by Luethi & Liechti (2020 [Ref 13]) notes that serotonergic psychedelics can produce serotonin toxicity-like presentations, especially in combination with serotonergic drugs.

### Psychological risks

No published documentation of persistent psychological adverse effects specific to allylescaline. Class risks include psychedelic-induced perceptual disturbances (HPPD), anxiety, and paranoia — common to the phenethylamine psychedelic class (Nichols 2004 [Ref 16]).

### Case reports

No case reports of adverse events, intoxication, or overdose specific to allylescaline were found in any database (PubMed, web search).

---

## Harm Reduction

No published harm reduction protocols specific to allylescaline exist. The following reflects class-level evidence:

**Set and setting:** Standard psychedelic precautions apply. A comfortable, safe environment and trusted companions are strongly recommended given the 8–12 hour duration [Ref 2].

**Start low:** The published dose range starts at 20 mg with documented activity [Ref 1, Ref 2]. Doses above 35 mg are explicitly unexplored in published literature [Ref 2].

**Drug interactions (CLASS WARNING — no allylescaline-specific data):**
- **MAOIs:** Monoamine oxidase inhibitors are generally contraindicated with phenethylamines; MAO normally metabolizes phenethylamines, and MAO inhibition can lead to dramatically elevated blood levels and serotonergic toxicity (class inference; no allylescaline-specific data)
- **Lithium:** Lithium combined with serotonergic psychedelics has been associated with seizure risk in case reports in the broader literature
- **Serotonergic drugs (SSRIs, SNRIs, triptans):** Risk of serotonin toxicity; SSRIs may also blunt or eliminate psychedelic effects via 5-HT₂A downregulation

**Testing:** Reagent testing is recommended (Marquis, Mecke, Simon's reagent). Allylescaline samples from grey-market sources were characterized by NMR in the 2015 PeakAL study [Ref 4], confirming structural identity of samples circulating in the research chemical market.

**FLAG for human review:** All drug interaction contraindications for allylescaline are based on class-level inference, not substance-specific data. A safety-critical "interactions" section must be clearly labelled as class-level/extrapolated.

---

## Tolerance & Dependence

### Tolerance

**Seed data values:** Buildup "almost immediately after ingestion"; half-life 3 days; full reset 7 days; cross-tolerance with "psychedelic" class.

These values are consistent with the known pharmacology of phenethylamine psychedelics but are not specifically published for allylescaline. The mechanism involves:

- **Rapid tachyphylaxis:** Psychedelic 5-HT₂A agonists develop rapid tolerance; de la Fuente Revenga et al. (2022 [Ref 17]) demonstrated tolerance in mice after a single administration of DOI within 24 hours
- **5-HT₂A downregulation:** Repeated psychedelic 5-HT₂A agonist exposure produces cortical 5-HT₂A receptor downregulation (Buckholtz et al. 1990 [Ref 18]); however, mescaline at standard doses did NOT reduce 5-HT₂ binding in this study, possibly suggesting the mescaline-class tolerance mechanism may differ from indole hallucinogens
- **Cross-tolerance:** Cross-tolerance between psychedelic 5-HT₂A agonists (DOI and LSD) is established in mice (de la Fuente Revenga et al. 2022 [Ref 17]); allylescaline would be expected to exhibit cross-tolerance with other serotonergic psychedelics

**FLAG for human review:** The specific tolerance half-life values (3-day half-life, 7-day full reset) in the seed data are likely extrapolated from the broader serotonergic psychedelic class and are widely used in harm reduction literature, but are not published specifically for allylescaline or mescaline.

### Dependence

Hallucinogens including phenethylamine psychedelics are considered physiologically safe and do not produce physical dependence or addiction (Nichols 2004 [Ref 16]). The seed data characterizes allylescaline as "not habit-forming" — this is consistent with published class pharmacology. No published allylescaline-specific dependence data exists.

---

## Interactions

No published drug interaction data specific to allylescaline exists. Known interactions from the seed data are blank. The following reflects class-level pharmacological inference:

**Serotonin syndrome risk:**
- **MAOIs (irreversible and reversible):** High risk — MAO inhibition blocks primary metabolic pathway of phenethylamines, dramatically increasing bioavailability and duration; concurrent use is potentially life-threatening (class inference)
- **SSRIs/SNRIs:** May reduce psychedelic effects via 5-HT₂A downregulation; serotonin syndrome risk at high doses
- **Triptans:** Serotonergic; additive risk

**CNS stimulation risk:**
- **Stimulants (cocaine, amphetamines, MDMA):** Cardiovascular and CNS additive risk
- **Lithium:** Case reports of seizures with lithium + classical psychedelics in literature

**FLAG for human review:** All interactions are class-level inference. No allylescaline-specific pharmacokinetic interaction data (CYP inhibition/induction profiles) exists. The allyloxy group's metabolism is unpublished — potential CYP3A4/CYP2D6 involvement by analogy with NBOMe series [Ref 12].

---

## Legal Status

| Jurisdiction | Status | Details | Source |
|---|---|---|---|
| United States | Unscheduled | Not explicitly listed in DEA schedules; potential Federal Analogue Act (FAA) applicability as mescaline structural analog | Web search |
| United Kingdom | Prohibited | Covered by Psychoactive Substances Act 2016 (in force 26 May 2016) | UK legislation [web] |
| Sweden | Controlled narcotic | Explicitly listed; effective January 26, 2016 | Web sources [Ref 15] |
| Switzerland | Controlled | Listed in Verzeichnis E of narcotics legislation | Web sources [Ref 15] |
| Germany | Controlled | Covered under analogue provisions of BtMG | Web sources |
| Japan | Controlled | Listed as controlled substance | Web sources [Ref 15] |
| Canada | Uncontrolled | Not listed in Controlled Drugs and Substances Act as of 2025 | Web sources |
| Australia | Status unclear | No specific scheduling found; covered under general analogue provisions in some states | Research gap |

**FLAG for human review:** The Australian and EU-member-state-specific (beyond Sweden/Germany/Switzerland) legal statuses were not confirmed from authoritative sources. The US Federal Analogue Act applicability has not been adjudicated in any published case.

---

## Clinical Trials

**No clinical trials found.** A search of ClinicalTrials.gov for "allylescaline" returned zero results. No trials are anticipated given the compound's unscheduled/under-researched status and absence of any IND or equivalent application in published sources.

---

## Community Feedback Analysis

**No community feedback was submitted in Part A2 of the brief.**

Standard procedure: no community feedback items to investigate or report.

---

## Gaps & Flags

### Critical data gaps

1. **No published binding affinity data:** No Ki or EC50 values at any receptor (5-HT₂A, 5-HT₂C, dopamine, adrenergic, etc.) have been published for allylescaline. All pharmacological class statements are structural analogy inferences. **[SAFETY-CRITICAL FLAG]**

2. **No published pharmacokinetic data:** No Tmax, Cmax, t½, bioavailability, urinary recovery, or metabolite data has been published for allylescaline in any species. PK section relies entirely on class-level mescaline data [Ref 7] and CYP inference from related phenethylamines [Ref 12].

3. **No published toxicity data:** LD50 unknown. Toxic dose unknown. No case reports of adverse events, intoxication, or overdose. Cayman Chemical's research product page states "physiological and toxicological properties not known" [Ref 20]. **[SAFETY-CRITICAL FLAG]**

4. **No published drug interaction data:** All drug interactions are class-level extrapolation. **[SAFETY-CRITICAL FLAG]**

5. **Dose range above 35 mg unsupported:** The seed data dose tiers extending to 60+ mg ("heavy") have no published primary source. Shulgin explicitly noted doses above 35 mg were "unexplored" [Ref 2]. The extended ranges likely derive from community reports, not controlled documentation. **[SAFETY-CRITICAL FLAG — doses above 35 mg have no published human safety data]**

6. **Onset discrepancy:** Brief states 45–240 minutes onset. PiHKAL self-reports document 10–50 minutes onset at 24–35 mg [Ref 2]. The lower bound (45 min) is already higher than Shulgin's fastest-onset report (10 min). The 240-minute upper bound has no published primary source. This discrepancy should be editorially reviewed.

7. **Leminger 1972 primary source unavailable:** The Leminger paper (*Chemický průmysl* 22:553, 1972) is a pre-digital Czech chemistry journal not indexed in PubMed or Crossref. It cannot be programmatically verified. All Leminger data is mediated through the CountYourCulture secondary source [Ref 14] and Shulgin's PiHKAL [Ref 2]. The original Czech text has not been located in translation.

8. **Mechanism of allylescaline's enhanced potency vs. mescaline:** The reported ~10× potency advantage over mescaline is based on self-reports, not controlled pharmacological studies. The mechanism (lipophilicity, receptor affinity, oral bioavailability differences) is unknown.

9. **Physical properties:** No melting point data found. Solubility data from non-peer-reviewed vendor sources only.

10. **Australian and non-UK/Sweden/Switzerland EU legal status:** Not confirmed from authoritative national sources. Research gap remains.

### Data relying on structural analogy (not substance-specific)

- All receptor pharmacology (5-HT₂A, 5-HT₂C agonism)
- All pharmacokinetic values (Tmax, half-life, metabolic pathways)
- All drug interactions (MAOIs, SSRIs, lithium, stimulants)
- Tolerance mechanism and timecourse
- Safety and adverse event profile

### Seed data confirmations

- Chemical identity (formula, MW, InChIKey, IUPAC name): ✅ Confirmed against PubChem
- PubChem CID: ✅ Confirmed (44719469; was blank in brief)
- SMILES: ✅ Confirmed (was blank in brief)
- Dose range 20–35 mg: ✅ Consistent with PiHKAL [Ref 2]
- Duration 8–12 hours: ✅ Confirmed by PiHKAL [Ref 2]
- Oral as primary and only ROA: ✅ Consistent with published records

### Seed data requiring editorial attention

- Onset 45–240 min: ⚠️ Inconsistent with PiHKAL (10–50 min) — needs review
- Dose tiers above 35 mg: ⚠️ No published primary source — generation agent should note this explicitly
- "Characterization: emerging" designation: ✅ Appropriate — very sparse published literature