AL-LAD
(6aR,9R)-N,N-diethyl-7-prop-2-enyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
Overview
AL-LAD belongs to Psychedelics / Ergolines.
Effects
- Broadly LSD-like, but frequently described as more clear-headed and less anxiety-provoking: 'lacking the vaguely sinister push' sometimes attributed to LSD
- Visuals are bright, colourful and cartoon-like, slow and smooth in motion, with somewhat less visual distortion than an equivalent dose of LSD
- A stimulating, euphoric body high with tingling. A shorter overall duration than LSD and a long, gentle come-down
Dosing & duration
Oral. Shulgin's TiHKAL account lists an oral range of roughly 80–160 µg. Community harm-reduction sources describe a common range around 100–225 µg. AL-LAD is about equipotent with LSD and active at ~100 µg, so dose it as carefully as LSD: volumetric dosing of a solution is strongly recommended for accuracy.
Dose ranges
~20 µg
50–100 µg
100–225 µg
225–350 µg
Duration
20–60 min
2.5–5 h
7–10 h
Chemical & Physical Properties
| Formula | C22H27N3O |
| Molar mass | 349.5 g/mol |
| State | Not reported |
| Melting point | Not reported |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 3.6 (predicted, XLogP3) |
| Solubility | Not reported |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 65527-61-9 |
| CAS (enantiomer) | |
| PubChem CID | 15227511 |
| InChIKey | JCQLEPDZFXGHHQ-OXQOHEQNSA-N |
| InChI | InChI=1S/C22H27N3O/c1-4-10-25-14-16(22(26)24(5-2)6-3)11-18-17-8-7-9-19-21(17)15(13-23-19)12-20(18)25/h4,7-9,11,13,16,20,23H,1,5-6,10,12,14H2,2-3H3/t16-,20-/m1/s1 |
| SMILES | CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)CC=C |
Synonyms
- ALLAD
- Allyl-LAD
- 6-Allyl-6-nor-LSD
- N6-allyl-6-norlysergic acid diethylamide
- 9,10-Didehydro-6-allyl-N,N-diethylergoline-8β-carboxamide
Pharmacodynamics & Biochemistry
A semi-synthetic lysergamide: the N6-allyl analogue of LSD (6-allyl-6-nor-LSD). Like LSD it acts as a potent full agonist at the serotonin 5-HT2A receptor, the target most closely linked to classic psychedelic effects. Binding work on the N6-substituted norlysergamides reports high 5-HT2/5-HT2A affinity (Kᵢ in the low single-digit-to-~8 nM range). AL-LAD is also described as interacting with other serotonin subtypes (5-HT1, 5-HT2C) and with dopamine D1 and D2 receptors, consistent with LSD's promiscuous lysergamide profile. In animals AL-LAD fully substitutes for LSD in drug-discrimination and produces the 5-HT2A-mediated head-twitch response. It is roughly 3.5× more potent than LSD in rat drug-discrimination yet only slightly less potent than LSD in the mouse head-twitch assay (ED₅₀ 174.9 vs 132.8 nmol/kg), and is reported to be about equipotent with LSD in humans.
Biological targets
- 5-HT2A
- D2
- D1
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| 5-HT2A receptor | Ki 8.1 nM | Rat |
| D2 receptor | Ki 12 nM | Rat (striatum, [³H]spiperone) |
| D1 receptor | Ki 189 nM | Rat (striatum, [³H]SCH23390) |
| 5-HT1B receptor | Ki 16 nM | Rat |
Pharmacokinetics
| Bioavailability | Not reported |
| Tmax | Not reported |
| Half-life | Not established in humans |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Presumed extensive hepatic metabolism typical of the lysergamides. The in-vitro metabolism of AL-LAD has been characterised analytically, but human pharmacokinetics, including a formal elimination half-life, have not been established. Its overall duration of action (~7–10 h) is somewhat shorter than that of LSD |
| Excretion | Not reported |
Toxicology & Safety
Not reported
AL-LAD is a potent psychedelic active at roughly 100 µg: accurate low dosing (ideally volumetric) is essential. Dedicated human safety and toxicity data are very limited. Risks are inferred from its close structural and pharmacological similarity to LSD. Expect a long experience (about 7–10 hours) with the psychological risks common to strong serotonergic psychedelics: anxiety, confusion, transient blood-pressure and heart-rate increases, and the possibility of precipitating or worsening psychosis in vulnerable people. As with all serotonergic drugs, combining it with other serotonergic agents can add to serotonergic load. Limited data must never be read as evidence of safety.[1]
Legal Status
US: Not federally scheduled. UK: Class A. DE: NpSG
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- Research.
- Recreational.
Sources & Evidence
- Nichols DE (2016). Psychedelics. Pharmacol Rev 68:264-355.
PMID 26841800 · doi:10.1124/pr.115.011478
- Pfaff RC, Huang X, Marona-Lewicka D, et al. (1994). Lysergamides revisited. NIDA Res Monogr 146:52-73.
PMID 8742794
- Watts VJ, Lawler CP, Fox DR, et al. (1995). LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors. Psychopharmacology (Berl) 118:401-9.
PMID 7568626 · doi:10.1007/BF02245940
- Brandt SD, Kavanagh PV, Westphal F, et al. (2017). Return of the lysergamides. Part II: Analytical and behavioural characterization of N(6) -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ). Drug Test Anal 9:38-50.
PMID 27265891 · doi:10.1002/dta.1985
- Halberstadt AL, Chatha M, Klein AK, et al. (2020). Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species. Neuropharmacology 167:107933.
PMID 31917152 · doi:10.1016/j.neuropharm.2019.107933
- PsychonautWiki: AL-LAD (dosage, duration & effects) CC BY-SA 4.0
- Wikipedia: AL-LAD CC BY-SA 4.0
- PubChem computed properties (CID 15227511)